Randy Roberts and Donna McKechnie
2026-03-30 20:00 - 23:00 (America/New_York) | The Studios of Key West, 533 Eaton St, Key West, FL, 33040, United States
Randy Roberts and Donna McKechnie

Spotlight Cabaret curated by Randy Roberts
Two showstoppers share one unforgettable stage. Broadway legend Donna McKechnie, Tony® Award winner for A Chorus Line, joins master entertainer Randy Roberts for an evening of song, dance, and sparkle. Together they celebrate the music, stories, and legacy of Broadway’s golden era for a night of pure theatrical joy.

My Maria - By Andrew Russell
2026-04-03 - 2026-04-04 | The Studios of Key West, 533 Eaton St, Key West, FL, 33040, United States
My Maria

By Andrew Russell

Directed by Morgan Green

Fri Apr 3 & Sat Apr 4, 8pm
A bold and highly theatrical play set in a fictional southern Midwest town, where Chuck, a sixty-year-old school resource officer, falls in love with a mysterious woman named Maria through country line dancing. When his actions during a mass shooting call his courage into question and bring his world tumbling down, can their love survive?

Annual Conch Republic Independence Celebration
2026-04-17 - 2026-04-26
Annual Conch Republic Independence Celebration!

It’s Fun FOR ALL And ALL For FUN
The 44th Anniversary of Our Independence!

Calling Conch Republic Patriots, Pirates and Partiers – Declare Your FUN-dependence!

The Founding of the Conch Republic
The Conch Republic was born on April 23, 1982, in response to a United States Border Patrol Blockade of the Florida Keys. Since the United States insisted on treating the Keys like a foreign country, Mayor Dennis Wardlow seceded from Union. Today we stand proudly as a community of who have “Sovereign State Of Mind” and as the “People who seceded where others have failed”.

All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Key West Pride
2026-06-03 - 2026-06-07
2026 Dates – JUNE 3rd – 7th
CELEBRATE ONE HUMAN FAMILY

The Key West Pride event is one of the largest and most popular LGBTQ celebrations in the United States. Full of vibrant energy, spectacular events, and fun Key West activities, this is an event not to be missed whether you’re a member of the LGBTQ community, a friend or simply looking to support the event’s One Human Family philosophy.
Support the Key West Community
Key West’s gay community dates back to the 1940s, when Tennessee Williams arrived to the little island with his longtime partner, Frank Merlo. Williams is credited for establishing Key West as an official gay vacation destination, and the Key West Business Guild, which has been promoting LGBTQ Travel to Key West since 1978, is a testament to his legacy.
2026 SCHEDULE OF EVENTS!
All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Kicking off Pride Week – Saturday, May 30th

6:30 pm – Key West Pride Follies at the Key West Theater
Join us for an outrageous, unforgettable night as the legendary Key West Pride Follies returns, bolder than ever with Dominic Paolillo and new co-host, Claire Caplan! This precursor to Pride tradition is one you won’t want to miss, featuring local talent showcasing a variety of acts, including singers, dancers, and more! Wear your favorite rainbow color and come ready to have a fantastic time! Tickets are now available HERE.

Key West Pride Begins – Wednesday, June 3rd.

Noon – Key West Business Guild Membership Luncheon: Pride Edition
More info coming soon!
5-8 pm – The GOLD Party @ Island House for Men
No clothing required, but wear something GOLD! Come celebrate 50 Years of Fabulous at the Best Gay Resort in The World! Gold crowns, tiaras, body paint, sequins, spandex- you name it- just make it GOLD! Tons of free appetizers served by Golden pool boys, free shots, giveaways, and 2-4-1 on all cocktails! $20 Donation benefits our friends @ Womankind. All gay, bi, queer, trans + brothers welcome.
5:30 pm –KEY WEST PRIDE KICK-OFF – The Key West Cooking Show – 291 Front Street (inside The Shops of Mallory Square, up the escalator) Presented by the Key West Business Guild and Gay Key West, this year’s Pride event carries the overarching theme of “Color the Island: A Celebration of Identity Through Color & Creativity.” Join us for a vibrant kick-off to Pride 2026 as we transform the island into a living canvas of self-expression, artistry, and community. Color the Island is more than an event; it’s an immersive celebration of identity, where every hue tells a story, and every voice adds to the theme. The celebration features local DJ Mr. Enjoy, local vendors, delicious food, and unlimited drinks! All included with your entry! Come ready to color the island with pride! This event is 21+ only. Tickets available HERE

Thursday, June 4th.

Noon – 4 pm – Rainbow Runway: Poolside Glam-Off at the Lighthouse Hotel – 902 Whitehead St
Celebrate Pride poolside in full color at our Rainbow Runway: Poolside Glam-Off. DJ Rude Girl will be setting the vibe. Calling all main-character energy only. Arrive ready to showcase your style because at 3pm, we crown the Best Poolside Look, followed by a champagne spray finale you won’t forget. Glitter optional. SPF required. Pride mandatory. 21+ event. Free entry.
6 pm – Key West Pride Annual Tea on the Sea on Fury Watersports – Opal Key Marina 241 Front St. Hop aboard Fury Water Adventures for one of Key West Pride’s most iconic traditions, a floating Tea Dance that sails straight into the sunset! With DJ Mr. Enjoy spinning grooves, you’ll dance across the deck as the sky lights up in rainbow hues. Your ticket includes unlimited beer, wine, champagne, margaritas, and tasty appetizers—so come thirsty, come hungry, and come ready to slay at sea. Check-in by 5:45 pm, for a 6 pm departure. Tickets available HERE
9 pm – Key West Local Bartender Competition at Bourbon St. Pub – 724 Duval St
Local bars are competing to be crowned the ultimate bartender champion for Pride 2026, along with earning bragging rights! Which bar will take home the prize this year? All are welcome. 21+ event. Free entry.

Friday, June 5th.

11 am – Key West Pride Brunch Sail & Swim aboard the Argo Navis – 0(Zero) Duval St.
Come out sailing in support of Gay Key West and Key West Pride Week! We’re hosting a brunch, sail, & swim at this festive fundraiser ~ a portion of every ticket sold goes back to Gay Key West! Come in your favorite color or representation of the rainbow to celebrate this year’s Pride theme, “Color the Island”, and you just might be crowned the 2026 winner of Argo’s Annual Pride Cossie Contest! Guests enjoy a delicious light brunch, Bottomless Mimosas, Bloody Marys, house made Sangria and Cocktails along with Miller Lite and local craft brews. During our first hour, we sail along the historic Key West shoreline, giving you a great vantage point to take in the sights of the island. Then we anchor the boat and get ready for fun in the sun and playtime in the water! After swim time enjoy a fresh water rinse, an ice cold towel for your face and a piece of pineapple to rinse the salt taste from your mouth. Finish the afternoon with another cool drink and a sweet treat– a perfect end to the day! Tickets are available HERE
12 pm – ALL WELCOME “RU WET” Annual Pool Party at Alexander’s Guesthouse – 1118 Fleming St.
We’re turning up the heat with Ms. Bouvee on hand serving fierce looks and fabulous fun for Drag Bingo you won’t want to miss. Enjoy poolside drag bingo, live musical performances, comedy, and audience interaction. Plus drink specials and a live DJ playing the latest hits!
12-5pm – Sausage Fest at Island House for Men – 1129 Fleming St.
The title says it all! Join the boyz of Island House for a naked sausage fest like no other! Gourmet sausages from around the world, served by our friendly pool boyz. Savor signature Stoli frozen drinks, & food specials! All gay, bi, queer, trans + brothers welcome.
4 pm – A Mojito Masterclass at Tropicado in La Concha Key West – 430 Duval St.
Join us at Tropicado Mojito Bar at La Concha Hotel for an immersive, hands-on mojito experience in the heart of Key West!
Shake, “slap”, and sip your way through the art of crafting the perfect mojito as you explore Papa’s rum, fresh ingredients, and the vibrant spirit of Havana. This interactive class is a must-do for cocktail enthusiasts, curious beginners, and anyone looking to elevate their island experience. 21+ event limited to 25 people. Ticket link coming soon!

8 pm – BERTHA: Grateful Drag hosted by Beatrix Dixie at the Key West Theater – 512 Eaton St
The world’s first Grateful Drag band, BERTHA is an all-star collective of queer and allied East Nashville talent coming together in wigs and full face for a good cause. Fronted by a harmony trio of Berthas and backed by a rocking all-Bertha band. Find out why Rolling Stone Magazine said “Nashville’s Bertha, gives The Dead an irreverent, joyful maker.”, and JamBase said “BERTHA: Grateful Drag is far from a gimmick. These musicians are the real deal and have some of the best harmonies and vocals of any Grateful Dead tribute act.” Doors open 7:00 pm. Tickets Available HERE
10 pm –Midnight Mass: A Heated Confession @ Island House for Men – 1129 Fleming St.
A party that has grown infamous since it’s inception. Swings, communal alter, huge projector screen. Lose your inhibitions and look your fantasy right in the eyes. Safe, sane, and smoking hot. All gay, bi, trans, queer + brothers welcome.

Saturday, June 6th.

11:30 am – Paint the Town Proud Pub Roll starting at Bobby’s Monkey Bar – 900 Simonton St.
Join us on the Old Town Trolley Tour for the “Paint the Town Proud Pub Roll”, an exciting adventure outside Key West’s historic and vibrant Gayborhood. This unique event celebrates the island’s LGBTQ+ cultural heritage while you enjoy specially curated Pride-themed drinks at each stop. Be sure to dress in your favorite color of the rainbow to win best dressed! We’ll kick off the tour at Bobby’s Monkey Bar, where you can enjoy delicious breakfast bites and a welcome drink. A cash bar is also available for mimosas, Bloody Marys, or any other drinks you might want to have before the tour begins!
The tour departs promptly at 1:00 PM. This event is 21+ only. Tickets available HERE

4 pm – “Celebration of Identity Through Color & Creativity” Street Fair on the 700-900 blocks of Duval Street
Celebration of Identity Through Color and Creativity Street Fair is a vibrant gathering honoring the beauty of self-expression, community, and love in all its forms. Stroll through a lively open-air festival filled with vendors, live music and dance performances. Enjoy delicious food from diverse vendors, connect with community organizations, and discover safe spaces designed for conversation, inspiration, and celebration. Whether you come to dance, create, learn, or simply soak in the joyful atmosphere, this event welcomes everyone to show up exactly as they are.
Bring your brightest outfits, your loudest cheers, and your truest self because when we celebrate identity through color and creativity, we paint a future rooted in pride, unity, and love. All welcome, family friendly event. VENDOR APPLICATION IS NOW OPEN!
10 pm – All Welcome Purgatory Party at Bourbon St. Pub – 724 Duval St.
Adult themed pool party where bad boys and bad girls come play. Purgatory is a fetish and poolside party. Fetish attire is encouraged. This event is 21+ and has a cover charge at the door.

Sunday, June 7th.

10 am – MCC Church Pride Service – 1215 Petronia St.
10 am – Unity of the Keys Pride Service – 1011 Virginia St.
11:30 am – Key West Pride Drunken Drag Brunch at Mangoes Key West – 700 Duval St.
Mangoes Drag Brunch has been proudly voted Top 10 Drag Brunch Shows in the USA by the Miami Herald. This high-energy, crowd-favorite event will be featured in their air-conditioned Ricky Ricardo Private Event Space, complete with a private bar and private bathrooms; the perfect setting to enjoy an unforgettable brunch experience in comfort and style. Mangoes offers a special à la carte brunch menu, featuring delicious brunch favorites available for purchase. After the show, stick around for a meet-and-greet and the opportunity to take photos with our local stunning drag queens. Ticket Options: VIP Tickets – VIP tickets include access to the fabulous drag show, the best seats in the house, and exclusive VIP swag take-home gifts. General Admission Tickets – General Admission tickets include access to the fabulous drag show with regular admission seating.
Important Information: This event is 21+ only due to current Florida state laws. No one under the age of 21 will be admitted. No refunds. Please double-check your purchase before clicking the buy button. All tickets are non-refundable, no exceptions.
Noon – HOT NAKED SUNDAY at the Island House for Men 1129 Fleming St.
After church, and before tea dance, comes Island House! A Gay Key West tradition for over 20 years! All gay, bi, queer, trans + brothers welcome.
7 pm – Color the Island Pride Parade
Join us as we celebrate the closing of Key West Pride 2026 with our annual Parade! The parade route will begin at the Quay at Truman Waterfront, continue down Whitehead Street to Front Street, turn right onto Duval Street, and finish at United Street. After the parade, we’ll make our way to La Te Da for the “last dance.” The parade line-up will begin at 5 pm. Participants interested in joining the parade MUST complete the application available on the website above.

Daily Activities

Museums: Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum, Audubon House, Oldest House and Garden Museum, USCGC Ingham Museum, Tennessee Williams Museum, Hellings Curry Museum/ Home of the Key West Woman’s Club, Ernest Hemingway Home & Museum
Land Activities: Key West Food Tours, iWitness True Crime Tours, Fort Zachary State Park, West Martello Tower, KW Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery, Key West Fine Wine, Key West Wildlife Center, Tart Tales.
Water Activities: Argo Navis, Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling, Hindu Charters, Land Boat Charters, Namaste All Day Key West , Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom III

CORALPALOOZA
2026-06-04 - 2026-06-07
A GLOBAL MOVEMENT FOR OUR CORAL REEFS!
To celebrate World Oceans Day every year, Coral Restoration Foundation mobilizes thousands of ocean lovers in Florida and around the world to take action to restore our planet’s disappearing coral reefs. Coral reefs are a vital part of our planet’s life support system, providing food and coastal protection for millions. Yet, they are vanishing at an alarming rate, threatening marine ecosystems and human communities worldwide.
Year after year, Coralpalooza makes waves with large scale action taking place over three days in Florida, and with reef-saving activities happening around the world as part of the Coralpalooza Community.
Recognized by the UN Decade on Ecosystem Restoration, and listed as a UN Ocean Decade event, we are shining a light on the urgent need for collaborative efforts to restore our planets’ coral reefs.
Dive Days in the Upper and Lower Keys are scheduled for June 4th, 5th and 6th. These are open to the public with a minimum SCUBA certification of Open Water.
(2026 Dive Days are SOLD OUT!)

Upper Keys Events
DIVE DAYS

Thursday, June 4th – AM & PM Dives
Friday, June 5th – AM Dive
Saturday, June 6th – AM & PM Dives

Coralpalooza Community Night & Bazaar
Friday, June 5 | 6 PM – 8 PM
New this year! The celebration continues in the Upper Keys with our Community Night & Bazaar—also serving as our annual dive social—at the iconic Caribbean Club. Connect with divers, conservationists, and ocean lovers while shopping sustainably minded local vendors, meeting marine nonprofits, and enjoying food trucks, lawn games, and live music at sunset.

Lower Keys Events
DIVE DAYS

Friday, June 5th – PM Dive
Saturday, June 6th – AM Dive

Coralpalooza Social – Key West
Saturday, June 6 | 6 PM – 8 PM
Join our Lower Keys divers and snorkelers as we celebrate the hard work accomplished underwater at the Southernmost Pint Brew Pub. Registered participants will receive a food ticket, and all are welcome to come learn more about Coralpalooza and connect with the community.
Coralpalooza at Key West Aquarium
Sunday, June 7 | 10 AM – 4 PM
Family fun! Coralpalooza wraps up in Key West with a special celebration of the Key West Aquarium’s 90th anniversary. Explore reef ecosystems and enjoy interactive presentations. Catch the swashbuckling Captain Coral show at 12 PM and 2 PM.

Summer Solstice Celebration
2026-06-08 - 2026-06-21 | Key West, Florida, Key West, FL, 33040, United States
JUNE 8-21, 2026

Join us for our 2026 summer solstice celebration

For two weeks, the Sunset Celebration transforms into a vibrant Solstice Festival filled with live entertainment, local art, interactive experiences, island-inspired food, and local non-profit
organizations. Celebrate the season with nightly festivities, community traditions, and
unforgettable sunsets in the heart of Key West.

Key Lime Festival
2026-07-01 - 2026-07-05 | Key West, Florida, Key West, FL, 33040, United States
2026 DATES – JULY 1 -5th
Welcome to the Key Lime Festival: America’s Favorite Citrus Celebration! In the Florida Keys we like to celebrate the things that make our islands unique. Citrus, eccentrics, people & pie. Our celebrations are fun, odd & unforgettable. Our people are too. Come on down to the birthplace of Key Lime Pie for a little taste and you’ll see what we mean. Love & Limes!

2026 SCHEDULE OF EVENTS!
All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Wednesday, July 1st
Key Lime Kick Off! Live Music & Spirited Key Lime Entertainment!
The Avalon | 1317 Duval St | 5 – 8PM
Welcome keynote speech by Key Lime Festival co-founder and Key Lime Pie Historian & Cookbook author, David L. Sloan. Toast with cocktails on the veranda and kick up your heels on Duval Street to our Americana band. FREE TO ATTEND! Full Cash Bar & Festival Merchandise Available For Sale.
Key Lime SPIRIT Pageant!
Help us cheer on the contestants in our 1st annual – “Key Lime Spirited Pageant!’ – OR enter the competition yourself if you’ve got the ZESTE! Individuals will compete to be crowned the Key Lime Festival Emperor or Empress! To enter the pageant, please email aandrade@southernmostresorts.com.
Living The Key Lime Life Dinner
Kaya Island Eats cordially invites you to join us for a celebration of the Key lime life we all enjoy here in paradise! A beautiful 4 course meal prepared by Chef Scott Taylor and the Kaya culinary team.
1st Course : Hurricane seasoned fresh Key west pinks and key lime cocktail sauce
2nd Course : Cuban Hand Roll / mojo Roast pork /Swiss cheese /pickle/ egg roll cilantro key lime sauce
3rd Course : Floribbean Fish – Locally caught fish, Jamaican jerk seasoned Mahi Mahi, Fresh Pineapple/mango salsa, Goat cheese / coconut saffron rice
*Chicken or Portobello options available
4th Course : Made from scratch Key lime pie
After dinner join us for live entertainment in the backyard bar.
5-9PM
$75/Person + Tax
Text or Call to book your reservation (305) 395-0213
Tropicado’s Havana Nights – Key Lime Cocktail Party
NEWLY REMODELED Tropicado @ Historic La Concha Hotel, 430 Duval St
Keep that Key Lime energy going! Salsa, rumba, and cha-cha the night away while you enjoy some specialty crafted key lime cocktails.
7-10PM
FREE

Thursday, July 2nd
Key Lime Bike Tours
Join Key Lime Bike Tours for an unforgettable ride through the island’s iconic landmarks and see the sights of the city from a local’s perspective! Hear captivating stories of old-time sailors and discover hidden gems. Cool off with a dip in the Atlantic, and savor a slice of award-winning key lime pie, the most famous dessert in all of the keys! Finish your ride with a champagne toast. Don’t miss this unique opportunity to explore the history and beauty of Key West—grab your tickets today for an adventure you won’t forget!
Tour starts at 9:30AM | 122 Ann St
Key Lime Pie & Champagne Toast included on the tour
$55

TICKETS

Key Lime Pie Hop
CHECK-IN LOCATION : Pilar Rum – Hemingway Social Club
Join your friends for a leisurely stroll through the town where Key Lime Pie was born with stops to sample variations of Key West’s favorite dessert. From classic to creative, your taste buds are guaranteed a good time on this popular culinary event. Sample the best of the best of our island’s Key Lime Pie!
Check-in 20 minutes prior to tour time
Tour Start Times:
• 11AM
• 11:30AM
• Noon
• 12:30PM
• 1PM
• 1:30PM
$55.00 *includes pie samples and a FREE Key Lime Festival T-shirt!

TICKETS

Truman Waterfront Farmers Market – Key-Lime-O-Rama
1-6PM
21 E Quay Rd, Truman Waterfront
Get ready for Key-Lime-O-Rama, a citrus-filled celebration at the Truman Waterfront Farmers Market timed perfectly with The Key Lime Festival week. Vendors will feature bright, tangy creations and Key lime-inspired specialties throughout the market—from desserts and beverages to creative culinary twists on the island’s signature flavor. You’ll also find fresh produce grown in Homestead, gorgeous orchids & native plants, artisan selection of seafood, meats and cheeses, pickles, honey, natural soaps, amazing sunsets and a great selection of Key West crafts, gifts and art. Come sample, shop, and enjoy a refreshing afternoon of local flavor along the waterfront.
Visit the Coast Guard booth for boater safety information, games, and giveaways!

US Coast Guard

Sunset Cocktails on The Cutter Ingham
21 Quay Rd, Truman Waterfront
6PM: Experience a live Search & Rescue Demonstration
7-9PM: music by the United States Coast Guard Band and a Sunset Reception on the USCG Cutter Ingham!
Enjoy Key Lime Cocktails and sample Key Lime desserts prepared by the United States Coast Guard Culinary Professionals.
*DONATION SUGGESTED

Wheeling & Dealing Hot Wheels Race
Mary Ellen’s Bar, 420 Applerouth Ln
Test your driving skills on our Applerouth Track. Epic thrills and revving creativity. Do you have what it takes to win the race?!?
4 – 6PM
Final Heat @ 5:30!
$10 **includes (1) FREE BEER and (1) FREE Key Lime Festival Bandana

TICKETS

Sloppy Joe’s Ultimate Key Lime Pie Smash Party!
Vote with Donations & Bid in our Live Auction to have some of your favorite Key West Local Celebrities and Sloppy Joe’s Staff get a Key Lime Pie to the face. Donations to benefit The Sloppy Joe’s Foundation!
Sloppy Joe’s is “Still The Best Party In Town!”
5:30 – 9:30PM
Pub Style Trivia with a Key Lime Twist
Southernmost Beach Resort on the Dewey Deck, 1319 Duval St
Join us for this one-of-a-kind trivia experience as teams of 6 or less battle it out to win prizes and earn the title of WISEST on the ISLAND!
Space is limited (50 players MAX) sign up NOW!
6PM Sharp
$20 – includes 5 rounds of trivia + (1) complimentary cocktail & chances to win prizes

TICKETS

Friday, July 3rd
5-Alarm Pie Challenge!
Alex Vega Key West Firehouse Museum, 1024 Grinnell Street
Stop by the historic and haunted Alex Vega Key West Firehouse Museum for a free sample of the hottest Key lime pie on the island. Specially prepared by Key West Key Lime Pie Cookbook author, David L. Sloan, the pie includes cayenne graham cracker crumbs, habanero cream, and a jalapeño topper. Bring your smartphone to check out the museums new haunted history audio tour or discover the fascinating history of firefighting in Key West.
10AM – 2PM
FREE – Donations are appreciated to support the museum
Key Lime-Tastic Pool Party
Blue Flamingo Resort, 3820 N Roosevelt Blvd
Break out your most key lime-y swim suit and get ready for the ZEST time of your life! The bar will be rocking Keylicious Food and Drink Specials all day. The DJ is bringing the tunes. Grab your bestie for a zesty photo shoot in the booth. There’s no lime-it to the amount of fun you’re going to have at this LIME-TASTIC Pool Party!
11AM – 2PM
FREE
Key Lime Sip & Stroll
If you like to drink & judge, this is the event for you! Decide who makes the best Key Lime cocktail on the island as multiple bars compete for your vote with the finest key lime margaritas and key lime ‘open’ cocktail in Key West.
* Check-in at our Key Lime Festival Hub: First Flight Restaurant, 301 Whitehead St. *
3 – 7PM
$55.00

TICKETS

A Citrus Affair at Four Flamingos, a Richard Blais Key West Kitchen
One-Night-Only Waterfront Key Lime Dinner Experience
Join us for an unforgettable evening of flavor and ambiance as renowned Chef Leo Minelli presents a four-course, Key lime-inspired menu at one of the region’s most breathtaking waterfront sunset locations.
From vibrant starters to the iconic Key lime pie, each dish is a bold celebration of tropical zest and culinary creativity. Let the flavors transport you—this is more than a meal, it’s an experience.
1st Course : Fresh Local Mahi-Mahi with Key Lime Leche de Tigre, Pickle Daikon and Cilantro
2nd Course : Miss Key West Pink Shrimp on Phyllo Spaghetti Dough with Habanero Labneh and Black Key Lime powder.
3rd Course : Creamy Risotto Loaded with Tender Lobster, Sweet Crab and Seared Scallops, Coconut and Fresh Key Lime Gremolata Add Local Catch of the day +$20 or Beef Tenderloin+ $25
4th Course : Key Lime Bourbon Espresso Martini garnished with our house made Key Lime Pie.
5-9PM
$85/Person + Tax & Gratuity
***Four Flamingos regular Menu will be available during regular business hours. Visit our website for menus.
Reserve your seat today and savor the zest of the summer.

Book A Reservation

Saturday, July 4th
Rotary Club of Key West 4th of July 5K Run/Walk
Join the Rotary Club of Key West for their annual 4th of July 5K!
All proceeds will benefit the Edward B. Knight Scholarship Fund providing vocational scholarships to Monroe County Students.
Race begins and ends at the Edward B. Knight Pier located at 1801 White Street.
Race Starts @ 7:30AM
$30 Kids 12 and under
$45 until June 30th @ Midnight
$50 July 1st – Race Day
NEW THIS YEAR : ALL PARTICIPANTS WILL RECEIVE A RACE T-SHIRT!

REGISTER HERE

Matt’s Stock Island Key Lime Brunch
Enjoy an unforgettable culinary experience at our dockside restaurant with unobstructed views of our state-of-the-art marina, good vibes, and your favorite cocktails.
Try our new Key Lime inspired menu items thoughtfully crafted for all the Key Lime lovers out there.
8AM-2PM

BOOK RESERVATION

Key Lime Vendor Village
10AM – 4PM | Southernmost Beach Resort – 508 South St
A Key Lime Lovers favorite place to be! Celebrate all things Key lime! Discover handcrafted goods, tropical art, and local treats while joining the fun of the world-famous Key Lime Pie Eating Contest. It’s sweet, tart, and uniquely Key West.
Be sure to pop in at Southernmost Beach Cafe for a cool beverage and some yummy food!
10AM – 2PM
Want to be a vendor at our Key Lime Vendor Village? Follow the link below:
https://keylimefestival.com/key-lime-vendors
World Famous Key Lime Pie Eating Championship
Southernmost Beach Café, 1405 Duval St. 10AM – 2PM
Do you have what it takes to be crowned the World Key Lime Pie Eating Champion? Register if you think you can devour a 9″ Key Lime Pie faster than the competition.
Registration at 10AM
Contest at 1:30 PM
FREE to Watch | PRE-REGISTRATION = $30 to enter the Championship | Day of Entry = $50
( ONLY 25 SPOTS AVAILABLE )
*If you are entering the championship, you must pay the entry fee and fill out the contestant form below.
ALL CONTESTANTS MUST BE 18 YEARS OR OLDER TO COMPETE.
All contest forms should be emailed to: keylimefest@gmail.com

REGISTER HERE

CONTESTANT FORM

NEW THIS YEAR! Key Lime Kid Zone
Southernmost Beach Café, 1405 Duval St. 10:30AM – 2PM
Slime Making & Slime decorating, Sing A-longs/Music, Story Telling & Reading, Crafting/Coloring, LEGOS, Beach Games and MORE….
@ 11:15 AM – Conch Shell Blowing Lessons so you can help us summon a Mermaid to the Shore! Bring your cameras, and get ready for some true Key West magic & Mermaid Photo Ops!
Dante’s 4th of July Pool Party!
Dante’s Key West Pool Bar & Restaurant, 955 Caroline St
Stars and Stripes rule the day! Grab your star spangled swim suits & head over for a day of drinks, live music and all the fun! A DJ will be spinning the jams from Noon – 6PM.
Doors open at 11AM | Party Starts at NOON.
FREE
The Rotary Club of Key West Presents:
Patriotic Grill Out Under the Fireworks
Indigenous Park, 1801 White St.
Bring the whole family to the Patriotic Party by the Ed Knight Pier.
Enjoy food, music, and of course, fireworks!
Grilling Hot Dogs and Burgers for purchase – Cash Bar Available
Food and Bar @ 4:30PM | Fireworks @ Dark

Sunday, July 5th
Matt’s Stock Island Key Lime Brunch
Enjoy an unforgettable culinary experience at our dockside restaurant with unobstructed views of our state-of-the-art marina, good vibes, and your favorite cocktails.
Try our new Key Lime inspired menu items thoughtfully crafted for all the Key Lime lovers out there.
8AM-2PM

BOOK A RESERVATION

Key West Artisan Market : Red, White, Blue & Green Edition
10AM – 2PM | Indigenous Park @ Higgs Beach, 1801 Atlantic Blvd
Keep the holiday weekend going at the Key West Artisan Market’s Independence Weekend pop-up. Stroll the market featuring island artists, handcrafted goods, local authors, and flavorful food vendors while enjoying live music and cool drinks by the water. It’s a festive way to wrap up the Fourth of July/Key Lime Festival weekend with community, creativity, and island vibes.
Free entry | Free parking | Pet friendly | Walking and Biking encouraged!
BYOB (Bring Your Own Bags)

VENDOR REGISTRATION COMING SOON!

Key Lime Pie Drop
Key West Lighthouse, 938 Whitehead St.
Come out to see Key West’s most creative minds attempt to outsmart gravity by finding a way to drop a Key Lime Pie from the top of the lighthouse to the ground… without damaging the pie. Try dropping your own pie, or just enjoy the spectacle from the ground.
11AM – 2PM
Check in for Pie Droppers is from 11AM-NOON.
Pie Drop starts promptly at NOON.
FREE to Watch | FREE to Enter the competition
Winner will take home CASH MONEY $$$
*If you plan to drop your homemade contraption from atop the Lighthouse, you must register below and fill out your contestant form describing what you’ve built!
All contest forms should be emailed to: keylimefest@gmail.com

REGISTER HERE

CONTESTANT FORM

JF Haden’s Battle of the Bartenders
Starboard @ The Marker Hotel, 200 Williams St
Get into the spirit of summer with JF Haden’s Key Lime Pie Liqueur and refreshing tropical cocktails at our Battle of the Bartenders event. This battle takes 6 amazing bartenders out of their “home” bars and puts them poolside where they will compete head-to-head. This competition highlights the best of bartending. You don’t want to miss this!
Battle begins at 2PM | Pool Party & LIVE MUSIC 2-5PM
FREE
Frozen Pie Pick-Up & Ship
Take Key West home with you.
Kermit’s Key Lime Pie Shoppe – 200 Elizabeth St. & 335F Duval St (305) 296-0806
Key West Key Lime Pie Co. – 511 Greene St. (305) 517-6720
Be sure to call ahead and reserve your Pie!
Shipping dates based upon availability.

Del Brown Permit Tournament
2026-07-12 - 2026-07-15
DEL BROWN 2026 TOURNAMENT
July 12 – 15, 2026
Celebrate a Fly Fishing Legend: Del Brown
The Del Brown Permit Tournament is an exclusive and prestigious fly fishing tournament. This annual event is dedicated to the man who made permit fishing with a fly rod famous: the late Del Brown, who caught 513 permit on a fly rod in the Florida Keys.
Test Your Mettle with 3 Days of Del Brown Permit Tournament Events
The permit is one of the most difficult fish to catch on a fly rod. The field is limited to just 20 boats, over 3 days of fishing. Part of the proceeds go to the Tarpon and Bonefish Trust for a better understanding of, and more effective conservation of Bonefish, Tarpon, and Permit, important species to Florida Keys tourism.

Schedule of Events

SUNDAY, JULY 12th
5 PM Cocktails & Dinner – South of the Seven – Mile Marker 17 at Sugarloaf Lodge
Kick-off for tournament, captains meeting, hand out tournament bags

MONDAY, JULY 13th
6:30 AM Sign-in – Breakfast, coffee and juice, pick up lunch to go
7:30 AM Boats may depart for fishing
3:30 PM Lines Out** – Scorekeeping, Appetizers and Drinks at South of the Seven
5:00 PM Scoring Closes – All releases must be recorded with scorekeeper
TUESDAY, JULY 14th
6:30 AM Sign-in – Breakfast, coffee and juice, pick up lunch to go
7:30 AM Boats may depart for fishing
3:30 PM Lines Out** – Scorekeeping, Appetizers and Drinks at South of the Seven
5:00 PM Scoring Closes – All releases must be recorded with scorekeeper
WEDNESDAY, JULY 15th
6:30 AM Sign-in – Breakfast, coffee and juice, pick up lunch to go
7:30 AM Boats may depart for fishing
3:30 PM Lines Out** – Scorekeeping, Appetizers and Drinks at South of the Seven
5:00 PM Scoring Closes – All releases must be recorded with scorekeeper
6:00 PM AWARDS IMMEDIATELY FOLLOWING LAST BOAT IN

Sloppy Joe's Annual Hemingway Days
2026-07-21 - 2026-07-25 | Sloppy Joe’s, 201 Duval Street, Key West, FL, 33040, United States
Hemingway Days
7/21/26 – 7/26/26

Key West’s Most Whimsical Tribute to Papa Hemingway

Welcome to the Key West’s most iconic and whimsical tribute to one of the greatest literary figures of the 20th century, Ernest Hemingway. Held annually in sunny Key West, this event celebrates Hemingway’s life in Key West and enduring legacy in a way that’s as unique and spirited as the man himself.
At the heart of the festivities is the Hemingway Look-Alike Contest, where participants worldwide don their best Hemingway-esque attire and compete to be named “Papa.” This isn’t just a contest of physical resemblance; it’s a celebration of Hemingway’s larger-than-life persona. Contestants are judged not only on their physical similarity to the great writer but also on their embodiment of his spirit and zest for life.
Adding to the excitement is the playful “Running of the Bulls” event, a nod to Hemingway’s love for Spain and its traditions. But in true Key West style, we swap real bulls for wooden sawhorses on wheels. It’s a spectacle filled with humor and camaraderie, perfectly encapsulating the fun-loving spirit of both Hemingway and Key West.
This event isn’t just for Hemingway enthusiasts or look-alikes; it’s a gathering that invites all to enjoy the vibrancy of Key West, the thrill of friendly competition, and the warmth of a community that knows how to celebrate life. Whether you’re a literature buff, a Hemingway admirer, or just searching for a good time, the Hemingway Look-Alike Contest is an experience you won’t want to miss.
Features of the Event:

Look-Alike Contest: A spirited competition where the resemblance to Hemingway is just the beginning.
Running of the Bulls: A humorous twist on a Spanish tradition, with Key West’s unique charm.
Celebration of Hemingway’s Legacy: Immerse yourself in the world of Ernest Hemingway through stories, and an atmosphere that echoes his adventurous life.
Community and Camaraderie: Meet fellow Hemingway fans and become part of a tradition that celebrates one of literature’s giants in the most joyous way possible.

Join us for an unforgettable event where the spirit of Ernest Hemingway is alive and well, and the essence of Key West’s fun-loving culture is on full display. We can’t wait to see you here!

2026 SCHEDULE OF EVENTS
All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)
Happening Throughout the Event

Lorian Hemingway Short Story Competition. The competition started in 1981 and has awarded over $70,000 to writers of merit. More information may be found at www.shortstorycompetition.com.
Daily Tours of the Hemingway Home & Museum at 907 Whitehead Street. Visit https://www.hemingwayhome.com for more information.
July 22-25, 2026, the Key West Marlin Tournament, offering cash prizes for top catches of marlin and other fish, attracts up to 75 registered boats and their crews. The tournament, held Wednesday through Saturday during the annual Hemingway Look-Alike Contest, is a world-class fishing event hosted at the Perry Hotel and Marina in the Lower Keys. More information is available at www.keywestmarlin.com.
July 25-26, 2026: Hemingway 5K Sunset Run (5K Sunset Race by Key West Half Marathon).

TUESDAY, July 21, 2026

10:00 a.m. – 4:00 p.m. “Hemingway Collection” Museum Day at the Custom House. Discover rare artifacts and memorabilia from Hemingway’s life, a full-size bronze of the author and 59 original pen-and-ink drawings by famed marine wildlife artist Guy Harvey that provide a visual narrative to Hemingway’s novel, “The Old Man and the Sea.” Key West Museum of Art & History at the Custom House, 281 Front St. Free entry to those who mention Hemingway Days at the admission desk. Visit www.kwahs.org.
7:00 p.m. Lorian Hemingway Short Story Competition Announcement and Reading & “The Beard Also Rises” Screening • “Beards Go To Cuba” Preview at Tropic Cinema, 416 Eaton Street

Celebrate the 127th anniversary of Ernest Hemingway’s July 21 birth — with the announcement and first reading of the winning entry in the renowned Lorian Hemingway Short Story Competition. Then “meet” the Papa Look-Alikes in “The Beard Also Rises,” a lively short film by Cassidy Rast and Odin Wadleigh … and view a sneak preview of their “Beards Go to Cuba,” debuting at film festivals in fall 2026.

WEDNESDAY, JULY 22, 2026

12:00 p.m. & 2:00 p.m. “Hemingway Cocktails” at the Key West Cooking Show, 291 Front St. upstairs. Learn to mix drinks, including the Hemingway Daiquiri, created especially for Papa, and the Death in the Afternoon that he invented. Also during the stir-and-sip session, discover memorabilia that recalls Ernest’s Key West life — from a model of his fishing boat Pilar to his buddy Charles Thompson’s fish mounts. Advance booking required; visit keywestcookingshow.com and use the code “PAPA10” for a $10 discount (valid only for 12 p.m. or 2 p.m. session on July 22).
5:00 – 7:00 p.m. Meet & Greet the “Papas” at Sloppy Joe’s Bar. Get to know the contestants and previous winners of the Sloppy Joe’s Hemingway® Look-Alike Contest.
7:30 p.m. “The Old Man and the Sea“ Tropic Cinema, 416 Eaton Street

View the classic 1958 film based on Hemingway’s Nobel Prize–winning book, “The Old Man and the Sea.” Spencer Tracy gives a compelling performance as Santiago, a Cuban fisherman whose battle with a giant marlin is an epic test of physical and spiritual strength.

THURSDAY, JULY 23, 2026

11:00 a.m. “A Hemingway Feast” at the Key West Cooking Show, 291 Front St. upstairs. Savor traditional Key West dishes from Papa’s era, and learn to prepare them, during an entertaining experience that spotlights local food and culture. The learn-and-dine adventure even features “grits-n-grunts,” mentioned in Hemingway’s Key West novel “To Have and Have Not.” Advance booking required; visit keywestcookingshow.com and use the code “PAPA10” for a $10 discount (valid only for the 11 a.m. event on July 23).
At 5:00 p.m. Round One check-in contestants must check in at the registration table to pick up their name tags and event shirts.
5:00 p.m. – 6:00 p.m. “Following the Fish: Hemingway in Key West” Comedy Key West, 218 Whitehead Street, #5

Raise a toast to Key West history and Ernest Hemingway’s angling legacy with Key West Art & Historical Society Curator Cori Convertito, Ph.D., during her popular “Happy Hour with the Historian” program. The Nobel Prize-winning author, who lived and wrote in Key West during the 1930s, immersed himself in Florida Keys game fishing. Convertito will share insights on both his angling exploits and his lesser-known conservation activities. For tickets, visit www.kwahs.org/whats-on/.

5:30 p.m. Introduction “Welcome” to the Contest by David Douglas, president of the Hemingway Look-Alike Society & Jeff Allen, CEO of Sloppy Joe’s.
6:00 p.m. Hemingway Look-Alike Society Scholarship Presentations. The society will announce the winners of its annual scholarships for the College of the Florida Keys students on stage at Sloppy Joe’s Bar.
6:30 p.m. Sloppy Joe’s 45th Annual Hemingway® Look-Alike Contest – Preliminary Round One on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round. (Live Auction benefiting the HLAS Scholarship Fund immediately following preliminary round one, while awaiting results) View Contest Results

FRIDAY, JULY 24, 2026

1:30 p.m. Papa Hemingway Look-Alike Fish-Off. Cheer your favorites as the Papas & Wannabes compete in this dockside catch-and-release challenge using traditional “Cuban Yo-Yos” at Conch Republic Seafood Company docks, 631 Greene Street. Free to watch. (Silent Auction benefiting the HLAS Scholarship Fund during Fish-Off)
5:00 p.m. Round Two Contestants Check in at the registration table to pick up the name tag and event shirt.
6:30 p.m. Sloppy Joe’s 45th Annual Hemingway® Look-Alike Contest – Preliminary Round Two on stage at Sloppy Joe’s. Contestants will be narrowed down to approximately 12 finalists to advance to Saturday night’s final round. (Live Auction benefiting the HLAS Scholarship Fund immediately following preliminary round two, while awaiting results) View Contest Results

SATURDAY, JULY 25, 2026

10 a.m. to 10 p.m. (Duval Street closure ) Caribbean Street Fair to benefit Literacy Volunteers of America (LVA) Monroe County, Inc. Key West’s annual Hemingway Birthday Celebration provides an excellent opportunity for Florida’s artisans and food vendors to display and sell their works during the one-day Caribbean Street Fair on world-renowned Duval Street. If you are interested in being a vendor, download the vendor application.
Noon: Photos with “Papas.” Hemingway® Look-Alikes, Wannabes, Papas, and Bulls provide a photo opportunity for fans. Greene Street outside Sloppy Joe’s.

HLAS will sell red berets and red bandanas (limited quantities) beginning at 12 Noon on Saturday. Those wishing to wear traditional white clothing with a red sash need to be prepared and bring their own clothing (these items are not sold).

1:00 p.m. Annual ‘Running’ of the Bulls. This wacky event, sponsored by Sloppy Joe’s Bar, features past “Papa” Hemingway® Look-Alike Contest winners dressed in their Pamplona best and a breed of “bull” found only in Key West. The fun takes place on Greene Street outside Sloppy Joe’s.
5:30 p.m. Finalist Contestants must check in at the registration table at Sloppy Joe’s.
6:30 p.m. Sloppy Joe’s 45th Annual Hemingway® Look-Alike Contest – FINAL ROUND with the ‘crowning’ of Papa 2026. (Live Auction benefiting the HLAS Scholarship Fund immediately following the final round, while awaiting results. View Contest Results

SUNDAY, JULY 26, 2026

9:00 a.m. – 1:00 p.m. Papa Birthday Bash at Sloppy Joe’s – Bloody Marys with Papas (cash bar), Photo Opportunities with Papa 2026 & Papa birthday cake at noon.
10:00 a.m. – 4:00 p.m. “Hemingway Collection” Museum Day at the Custom House. Discover rare artifacts and memorabilia from Hemingway’s life, a full-size bronze of the author, and 59 original pen-and-ink drawings by famed marine wildlife artist Guy Harvey that provide a visual narrative to Hemingway’s novel, “The Old Man and the Sea.” Key West Museum of Art & History at the Custom House, 281 Front St. Free entry to those who mention Hemingway Days at the admission desk. Visit www.kwahs.org.
1:00 p.m. – 4:00 p.m. “Papa’s Tales” Storytelling Competition, Hemingway Social Club @Hemingway Distillery, 201 Simonton Street (Corner of Greene and Simonton)

Saluting Ernest’s storytelling skill, this fun-filled contest is for tale-spinners who can enthrall audiences with a spoken-word story of three minutes or less. Entrants in two competition categories will be judged on criteria including style, delivery, and originality. Entry is free, and the grand prize includes the prestigious Barrel Head Trophy. https://www.papaspilar.com

Key West Marlin Tournament
2026-07-22 - 2026-07-25
Celebrating its 45th year, the 2026 Key West Marlin Tournament, featuring $50,000 in cash prizes in the Marlin Division and more in the Fun Fish Division, is set for July 22 -25, 2026. The tournament, coinciding with the annual Hemingway Days Celebration in Key West, Florida, is a world-class fishing event drawing anglers eager to test the waters on “The Wall.” In addition to spectacular fishing and prizes, the event features nightly festivities, including the infamous Captains dinner, dinners on location and an awards banquet. Entries are limited to the first 75 boats—register now to ensure your spot.

2026 Key West Marlin Tournament Schedule of Events
Information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Wednesday, July 22
4:00pm – 6:00pm Tournament Registration
DoubleTree Resort by Hilton Hotel Grand Key – Key West
6:00pm – 7:00pm Captain’s Meeting/Cocktails
DoubleTree Resort by Hilton Hotel Grand Key – Key West
7:00pm – 8:00pm Auction & Raffle/Reception
DoubleTree Resort by Hilton Hotel Grand Key – Key West

Thursday, July 23
7:20am Boats assemble for traditional Bimini Start
7:30am Bimini Start
8:30am Lines in the water
4:00pm Lines out of the water
4:00pm – 6:00pm Weigh In
The Perry Marina (formerly Stock Island Marina Village)
6:00pm – 8:30pm Dinner @ Hogfish Bar & Grill

Friday, July 24
7:30am Boats leave control area for day two of fishing
8:30am Lines in the water
4:00pm Lines out of the water
4:00pm – 6:00pm Weigh In
The Perry Marina
6:00pm – 8:30pm Dinner @ El Siboney

Saturday, July 25
7:30am Boats leave control area for day three of fishing
8:30am Lines in the water
3:00pm Lines out of the water
3:00pm – 5:00pm Weigh In
The Perry Marina
6:30pm – 7:30pm Cocktails and Silent Auction @ DoubleTree Resort by Hilton Hotel Grand Key – Key West
7:30pm – 10:00pm Awards Banquet Dinner and Awards @ DoubleTree Resort by Hilton Hotel Grand Key – Key West6

Key West Lobsterfest
2026-08-05 - 2026-08-09
Get Ready to Crack! Key West Lobsterfest 2026 Dates are Set!

The wait is officially over! Get your butter warmers ready because we are thrilled to announce the dates for the biggest and tastiest summer celebration on the island: Key West Lobsterfest 2026 is happening from Wednesday, August 5th through Sunday, August 9th!
Join us for five unforgettable days as we celebrate the opening of the Florida Spiny Lobster season with an island-wide party. From the savory kickoff Lobster Boil to the massive Duval Street Fair with live music and endless crustaceans prepared every way imaginable, this is the ultimate crustacean celebration.

History of Key West Lobsterfest

Born from a Brawl (Over Lobster, No Less!)

Believe it or not, Key West Lobsterfest started with a friendly (or maybe not-so-friendly) dispute. Two friends couldn’t agree on who made the best Lobster Chilau, a Key West staple. What else to do but settle it with a cook-off? The inaugural throwdown went down in the courtyard of Rick’s & Durty Harry’s Entertainment Complex, with secret family recipes and judges galore. The event was such a hit (though we’ll keep the winner a secret), they knew they had to take it bigger. The next year, Lobsterfest moved to the bustling Duval Street, welcoming more participants, spectators, and sponsors than ever before. Fast forward to today, and this epic food fight has transformed into a 4-day extravaganza that takes over the entire island!

KEY WEST LOBSTERFEST 2026 28th Annual
All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)
WEDNESDAY, AUGUST 5
6:00 PM – 9:00 PM Key West Lobsterfest Kick-Off Party Rick’s & Durty Harry’s Entertainment Complex 202 Duval Street, Historic Old Town
Home of the inaugural Lobsterfest — this is where it all began with a contest for the best lobster dish on the island. Join us to kick off the 28th Annual Key West Lobsterfest. We need to empty the freezers to make room for freshly caught lobster!
Enjoy amazing lobster pizza and drink specials featuring our Official Sponsors Sun Cruiser Iced Tea and Cuervo 1800 Tequila.

THURSDAY, AUGUST 6
6:00 PM – 9:00 PM Lobster Boil at The Porter Mansion Courtyard – 429 Caroline Street, Historic Old Town
Join us for our annual seafood lobster boil in a beautiful Key West setting with a full bar, music, and delicious food.

Fresh lobsters
Jumbo Key West shrimp
Red skin potatoes
Fresh corn on the cob
Fresh baked jalapeño corn bread & melted butter

Each ticket is good for one guest’s admission and meal.

FRIDAY, AUGUST 7
3:00 PM – 6:00 PM Pool Party at The Marker Resort – Key West Harbor Resort – 200 William Street
Free Admission – Relax and soak up the fun.
8:00 PM – Midnight Lobsterfest Duval Pub Crawl Check-in: The Marker Resort Pool Bar, 200 William Street
Join us for the 28th Annual Lobsterfest Pub Crawl! The fun starts immediately after sunset and goes until midnight.
What’s included:

Official Lobsterfest T-shirt
Souvenir lanyard
Amazing drink specials on Sun Cruiser Iced Tea and Cuervo 1800 Tequila at participating bars

Tickets: $25 in advance / $30 at the door. A portion of proceeds benefit the Key West High School Scholarship Fund. Pick up your T-shirt, lanyard, and crawl instructions at the Marker Resort Pool Bar on August 7th from 3:00 PM – 7:30 PM. All items must be picked up in person.

SATURDAY, AUGUST 8
Noon – 11:00 PM – Street Fair & Concert 100–500 Blocks of Duval Street – Free Admission
Arts & crafts, merchandise, and more lining Duval Street all day.
Local bars and restaurants will be serving fresh Florida Lobster — everything from appetizers to full meals. No entrance fee; food and drinks sold individually.
Local bars will also be set up on Duval Street featuring ice-cold Corona, Blue Chair Bay Rum cocktails, and more.
Live Music Lineup:
1:00 PM Just George – Duval St. & Greene St.
3:00 PM Fried Newt – Main Stage
5:30 PM Jordan Oaks – Main Stage
8:00 PM The Durtbags – Main Stage — then continuing late night at Durty Harry’s

Key West Rum Fest
2026-08-10 - 2026-08-16 | Key West, Florida, Key West, FL, 33040, United States
Key West Rum Fest 2026 — August 10–16
The Florida Keys’ Key West Rum Fest returns August 10–16, 2026, with a week of global rum tastings, live music, culinary events, and island excursions. Proceeds benefit MARC Inc., a Keys-based nonprofit serving adults with developmental disabilities. Set against the backdrop of Key West’s tropical island culture, the festival pairs premium rum tastings from around the world with live performances, food-driven experiences, and themed excursions. Every ticket supports MARC Inc.’s mission to provide programs and services for adults with developmental disabilities in the local community.

Key West Rum Fest 2026 — Schedule of Events

Subject to change and errors and omissions – confirm on the official website for the event!

Monday, August 10

Day Trip to Bahamas — Roundtrip from Key West airport. Arrive by 7 AM, return by 6 PM. Passport required. (Waitlist only — text Neil at 910-599-6430)

Tuesday, August 11

Day Trip to Cuba — Roundtrip from Key West airport. Arrive by 7 AM, return by 6 PM. Visit the Hemingway home, the original Pilar boat, and Hemingway’s favorite bars. Passport required. (Waitlist only)

Wednesday, August 12

Day Trip to Cuba — Same itinerary as Tuesday; lunch and “other goodies” included
Sunset Trip, 6:30–8:30 PM — Leaves Garrison Bight. Daiquiri bar with Neil and Jess (Coasting Cocktails), visit to the site of Hemingway’s bar at Cottrell Key, rum & ice cream, custom hat for each attendee, dolphin viewing. Tank-top dress code. Available only via Water Package.

Thursday, August 13

Day Trip to Cuba (waitlist only)
5-Course Luncheon & RUMposium — At Casa Marina Hotel, with rum ambassadors Ian Burrell, Jeff “Beachbum” Berry, and Ed Hamilton
Reggae Pool Party, 2–4 PM — More details to come. No tickets necessary.
Meet the Owners, 4:30–5:30 PM — SALT Gallery, 209 Simonton St (next to Pilar Distillery). Neil’s new artwork on display and for sale. No tickets.
Sunset Sail Kickoff — Check-in 5:30 PM, boarding 6:00 PM. Meet at First Legal Distillery for a tour and complimentary piña colada, then walk to board the Fury (corner of Greene & Elizabeth, by Conch Republic Seafood Co.). Sunset sail with First Legal Rum Distillery and the Cory Heydon Band.
After Party at Tiki House, 9 PM — Featuring Worthy Park Rum. 21+. No tickets needed.

Friday, August 14

Day Trip to Cuba (waitlist only)
Sandbar Trip, 9:30 AM–1:30 PM — Leaves Garrison Bight. All cocktails included; live music by Dawson Wright with Key West Cocktail Cruises. Sponsored by Bombarda Rum. More info coming soon.
Rum Fest Book Signing — Time TBA. With rum authors Ian Burrell, Jeff “Beachbum” Berry, and Shawn Martin. Rum tasting with Down Island. Free admission.
“Landsharks at Lagerheads” — Cliff Cody, 2–2:30 PM — Live at Lagerheads Beach Bar
Mojito Pool Party, 3–6 PM — Marker Resort Pool Bar, custom mojito sponsored by Nauti Beach. Free admission; donations accepted for MARC House.
Meet & Greet Jesse Rice Concert, 3:30–5 PM — Key West Theater, max 60 people
Papa’s Pilar Rum Dinner — Time TBA. Tropical flavors and rum culture, tickets via Hyatt Centric.
Cliff Cody and Sharese (Local Artists) — Doors 7 PM, ends ~10 PM. Opener: Dawson Wright. Includes the 2026 Rum Cake Competition (call/text Neil to enter).
After Party at Sloppy Joe’s, 10 PM — 21+, no tickets needed

Saturday, August 15 (National Rum Day)

Sandbar Trip, 9:30 AM–1:30 PM — Leaves Garrison Bight. All cocktails included; live Dawson Wright music with Key West Cocktail Cruises. Sponsored by Marsh House Rum. More info coming soon.
Rum Lunch, 11 AM–1 PM — Hot Tin Roof. Agricole class with Ed Hamilton. $100 includes gratuity.
Grand Tasting, 2:30–5:30 PM — Key West Theater (3:30 entry for general admission). 40+ vendors. 100% of proceeds benefit MARC House.
Jesse Rice in Concert with Full Band — Berkley Lindley 7–7:15 PM, Dawson Wright 7:15–8:05 PM, Jesse Rice 8:05 PM onward
Saturday Night VIP After Party, 10:30 PM–close — Live music by Jesse Rice
“After-After Party” — Time and location not published. Word of mouth only; reach out to Neil.

Sunday, August 16

Rum Brunch with Bahama Bob, 11:45 AM–2 PM — Hot Tin Roof. Rum cocktails sponsored by Rhum Clement.
Going Away Party, 1–4 PM — Southernmost Beach Resort @ Pineapple Pool. No tickets necessary.

Key West Tropical Heat
2026-08-12 - 2026-08-16 | Key West, Florida, Key West, FL, 33040, United States
Tropical Heat is the HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties, pool parties, clothing optional events, and adult-oriented entertainment promise to be HOT! August on our tropical island is always HOT, but during Tropical Heat it promises to be even more so! What better way to experience our tropical paradise than joining us for 5 days with hot guys!? In addition to all our scheduled events, you can also enjoy our many other activities on land and sea!

Tropical Heat 2026 Schedule of Events

Wednesday, August 12th

5 PM– Cowboy Ken’s PINK Pool Party AND Kick-off @ Island House – 1129 Fleming St.
Think pink at the southernmost mojo-dojo-casa-house! Pink cowboy hats, pink hankies, pink speedos, OR LESS! Just make it PINK! Free appetizers and ½ price cocktails. VIP band holders can also pick up their bands at this events. Bands can also be picked up at the Gay Key West Visitor Center at 808 Duval St. through Tropical Heat between the hours of 9 am and 5 pm. For more info call (305) 294-4603.

Thursday, August 13th

10:30 AM – All Male Day Trip 🏳️‍🌈Ages 18+ • 4 Hours • BYOB *Snorkel, Sandbar or Kayak on Blu Q
Trip includes:

All Male + Clothing Optional
Snacks & Water Included, BYOB
Snorkel & Kayak Gear Included
Captains-Choice: activities tailored to the day’s weather conditions. We all want to have an amazing Key West day on the water!
Free Cancellation up to 6 days (144 hours) prior to scheduled departure time.
Bring a towel, and feel free to bring your own drinks! Our amazing crew will make sure your drinks stay cold in our coolers. They’re great at keeping track of who brought what and will keep you refreshed all day.
**Sandbar and Snorkel is our typical day on the water, but on certain weather and tide days, it can be tough to go to a sandbar, so we offer the option to kayak instead.

Tickets are available HERE

9:30 PM – Nightly Karaoke at Bobby’s Monkey Bar – 900 Simonton St
Unpretentious dive bar at 900 Simonton St in Key West (a block off Duval), known island-wide as one of the best karaoke spots in town. Karaoke runs nightly from 9:30 until late, with the place typically just getting going around 10pm and rocking by 11.

10:00 PM – Dancers on The Bar at Bourbon St Pub – 724 Duval St
The Bourbon St. Pub has been known all around the world for its Hot Men. And you can catch them each and every night on top of the bar for your viewing pleasure, starting at 10 PM.

Friday, August 14th

10:30 AM – Tropical Heat Snorkel Trip @ Blu Q Key West – 120 Margaret St.
If you haven’t set sail on Blu Q yet, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel, kayak, swim, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable, with their warm smiles, expert guidance, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets available HERE

1 PM – 5 PM Splash Pool Party @ Bourbon St. Pub – 724 Duval St.
Join World Famous Puddin’ Tane for some fabulous pool games and get a chance to meet the Adult Stars of Saturday Night’s Big ‘O’ Party while you beat the heat with ice cold drink specials from Key West Pride’s award-winning bartenders! Entrance and free clothes check included with your weekend pass bracelets! $20 or FREE

9PM – 4AM Heat Stroke: Leather Gear and Underwear Party @ Saloon One – 504 Petronia St
Whether you’re rocking your favorite leather, stripped down to your best underwear, or somewhere in between, this is your space to let loose, connect, and own the night. Expect pulsing beats, a bold crowd, and an unapologetically sexy atmosphere. Dress to impress, or undress to express.

Saturday, August 15th

10:30 AM–Enjoy a 4-hour Male All Day Trip with Blu Q Key West.
If you haven’t set sail on Blu Q yet, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel, kayak, swim, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable, with their warm smiles, expert guidance, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets are available HERE

12 PM –Five-Alarm Pool Party@ Island House – 1129 Fleming St
All fireman report to the pool deck for this high-energy firefighter themed pool party! Slide down the pole and get ready to get blasted by our pool boy CO2 cannon! Expect hot men & cold cocktails to make the perfect sizzling summer memory with friends!

10 PM – The Big “O” Exhibition @ Bourbon St. Pub – 724 Duval St.
A Voyeurs Dream Come True! The biggest blow out of the weekend! Foam party. Play areas. Pool & Jacuzzi. Hot Exotic Dancers and Adult Industry Performers.
Live Exhibition Shows. Free entry with your VIP bands, or $20 for non pass holders at the door. Free clothes check!

Sunday, August 16th

12 PM –Hot Naked Pool Party@ Island House – 1129 Fleming St
After church, and before T-Dance, comes Island House! For over two decades, this party brings visitors and locals together in true Gay Key West spirit! Hot-Naked-FUN!

Daily Activities

Museums: Ernest Hemingway, Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum, Audubon House, Oldest House and Garden Museum, USCGC Ingham Museum, Tennessee Williams Exhibit.
Land Activities: Key West Food Tours, Up the Keys Eco Tour, Fort Zachary State Park, West Martello Tower, A & M Scooter Rental, Key West Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery, Perky’s Key West Excursions.
Water Activities: Argo Navis, Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling. Land Boat Charters, Off the Charts, Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom.

Key West Womenfest
2026-09-02 - 2026-09-06
Experience the ultimate girls’ weekend at Key West Womenfest

Key West Womenfest is an annual end-of-summer festival celebrating lesbians and attracting thousands of women from around the globe.
September 2 – 6th, 2026

Five Days of Celebration in Paradise! Get ready to turn up the volume and celebrate bold, brilliant, and iconic women through the ages! Womenfest is back for another unforgettable year in paradise—five days of connection, empowerment, and celebration designed by women, for women. This year’s theme, “Decades of Divas,” honors the legendary trailblazers, pop culture queens, and everyday divas who’ve shaped our lives—from disco to digital, retro to revolutionary. Expect dazzling themed parties, soulful music, inspiring workshops, poolside fun, and the kind of community that makes Womenfest truly magical. Whether you’re channeling your inner Taylor Swift, Meg The Stallion, Madonna, Beyoncé, or your own personal diva, Womenfest is the place to shine.
Mark your calendar, gather your crew, and come celebrate the divas of every decade—especially you.

Celebrate Key West’s Open-Minded Lifestyle
Themed parties, specialty cocktails, women-only drag shows, tournaments and competitions, stand-up comedy, entertainment, live music, dancing and culinary events make these four days of events an experience not to be missed. A packed schedule of events ensure that every stripe of Womenfestivarian has an activity to enjoy, but one of the best experiences is lounging on a Key West beach with a good book and a cold drink.
Insider’s Tip: Don’t wait to book your Key West vacation rental. This is a popular event!

2026 Schedule of Events

Information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)
Wednesday, September 2

Noon – 1 pm — Key West Business Guild Membership Luncheon
6-8 pm — WOMENFEST 2026 — Lost Women In the Arts! Our official Welcome Party

Thursday, September 3

12 – 3 pm —6th Annual Corn Hole Tournament & Indoor Games. Sign up coming soon! American Legion Post 168 – 803 Emma St.
4 pm — HAPPY HOUR
6 pm — Fourth Annual “Women, Words, & Art Poetry Reading and Art Exhibition”
6 pm — Argo Navis presents the annual Womenfest Sunset Sail
9 pm — GrEEEn 60’s/70’s Hippies Party. Enter a world celebrating all things greeen! Dress in your best greeen hippie attire and dance the night away with the island’s best go-go dancers! Sponsored by the Greeen House – We spell it with 3 E’s so that you can’t say it without smiling, and that’s the goal, right?Birdcage Cabaret – 504 Angela St.

Friday, September 4

8-9 am — Early Bird Clean Up with Plogging the Keys, presented by Key West Womenfest. Join us for 1 hour to pick up litter. Vests, gloves, buckets, and pickers are provided. One hour makes a difference in keeping Key West Beautiful. Meet us at 808 Duval Street at the Gay Key West visitor center. Bagels, danish, and coffee will be provided by Goldman’s Deli afterward!
9:30 AM-11:30 PM— Join Key Lime Bike Tours for an unforgettable journey through the streets of Old Town Key West, a tour specially designed for Womenfest celebrating influential women! On this tour, you will discover the rich history and culture of Key West, while learning about the remarkable women who have made an impact on this beautiful island. Our knowledgeable and friendly guide will lead you on a leisurely bicycle ride through the charming streets of Old Town, stopping at significant landmarks and hidden gems along the way. As we ride through the picturesque neighborhoods and historic sites, you’ll hear stories of remarkable women who have called Key West home. At the end of your tour, we’ll finish with a delicious slice of Award Winning Key Lime Pie! Purchase tickets HERE.
11 am — Clothing optional Sandbar Snorkel trip on the Blu Q. We will set sail on the Blu Q Catamaran to one of many remote reefs off the Florida National Marine Sanctuary for snorkeling with tropical fish and various marine life. Afterward, you are taken to a secluded sandbar where you can swim, or just relax in the crystal clear waters of the Keys. Get 10% off with the code WomenFest25. Purchase tickets HERE.
12 pm — All welcome pool party – Bourbon St. Pub – 724 Duval St.
2 – 4 pm — Y2K Jell-O Wrestling Match hosted by your referee, BruceKey @AquaPlex. Watch as participants take to the ring for some friendly, competitive Jell-O wrestling. Enjoy a fiery, high energy atmosphere, cool AC and ice cold drinks available! **This is strictly a private event and only reserved for Womenfest participants. Wanna be a participant? Please email BruceKey at brucekey6969@gmail.com
3:30 – 5 pm —Love in A Flash: A Sapphic Speed Dating Experience. Get ready to spark connections in a flash! Join us for an electrifying afternoon of sapphic speed dating designed for women who love women. Whether you’re looking for love, laughter, or just a new friend, this is your chance to meet incredible people in a fun, low-pressure environment. Expect quickfire conversations, cheeky icebreakers, and plenty of opportunities to find your next crush—or maybe something more. Come as you are and leave with butterflies… or at least a great story.
Open to lesbian, bisexual, queer, pansexual, trans, and questioning women
Fun prompts to keep the convo flowing
Cocktails, mocktails & mingling after rounds
Because sometimes, all it takes is a spark. Let love strike. Entry is a donation at the door. To participate, sign up HERE
5 – 6:30 pm — Marjory Lee & The Misspellings “90s Female Alt Rock Band” Blast to the past Cover Show! Alanis, Gwen, Melissa, Sheryl, Fiona, Tracy, Joan…..gangs all here! Don’t miss this tribute to the badass female musicians of the 90s and all the closet doors they kicked down! Marjory Lee is a full-time local musician in Key West bringing ALL the lady love you can handle. Free event. RamHead Southernmost – 804 Whitehead St.
9 pm — Divas Through the Decades: A Celebration of the Lavender Ladies of Music History, produced by Marjory Lee.
Join us for a high-energy concert celebrating iconic women in music through many generations. Featuring powerhouse local vocalists and unforgettable hits, this show brings the evolution of women’s artistry to life. One decade, one diva at a time. This event is all-welcome with limited seating. American Legion Post 168 – 803 Emma St. Tickets available HERE

Saturday, September 5

10:00–11:30 AM | Womenfest Fragrance Making Class. Smells Like Teen Spirit. Create your own signature scent in this hands-on, guided perfume-making class inspired by the Decades of Divas. With access to over 300 oils from our luxury fragrance organ, you’ll blend, mix, and layer your way through the eras to craft three custom fragrances—then bottle your favorite in true diva style. Whether you’re channeling disco glam, 80s edge, or 90s grunge, this experience is all about expressing your era through scent. Tijon Key West – 335 Duval Street, Suite E. Your experience includes:
• A 55ml bottle of your personalized fragrance
• A VIP Tijon gift bag (valued at $60)
• A class certificate to mark your creative journey
• And of course, a champagne toast to celebrate your inner icon! Reserve your spot Here! This event is limited.
12-3 PM — Join us for the Official Womenfest Pool Party at Lighthouse Hotel hosted by the fabulous BAM with DJ Erika, who will be turning up the heat. Soak up the sun while dancing through the decades!
Start the fun with a complimentary Bad Bitch Rum cocktail—because your poolside presence deserves a proper toast.
Enter our raffle and score some seriously fun giveaways benefitting a great cause.
Enjoy games like our famous water balloon toss, poolside challenges, and more—because this party doesn’t just float, it slays.
Bring your best suit, boldest energy, and a few friends ready to party. Let’s make waves, divas! – Lighthouse Hotel – 902 Whitehead St
3 PM —Rainbow History Trolley Tour — Womenfest Edition: Celebrate Womenfest with an unforgettable journey through Key West’s vibrant LGBTQ+ past and present! Hop aboard our Rainbow History Trolley Tour, we will take you through the most iconic queer landmarks. and fully narrated by expert tour conductor – SKIPPPER. Ticket link HERE.
8 PM— Decades of Divas 80’s Prom. Dress to impress in your best 80’s diva attire—Madonna, Whitney, Prince, or full-on prom queen realness. We’ll have a photo booth, themed cocktails (and mocktails!), and DJ Rude Girl is back providing the 80’s hits to keep you dancing all night long. It’s your time to shine—so grab your date, your crew, or fly solo and strut into prom like the icon you are! Hosted by the glittery empress, Chantal P. Join us for Decades of Divas: ’80s Prom—a night where neon reigns, glitter rules, and everyone is the star of their power ballad. We’re talking teased hair, shoulder pads, and dance moves that don’t quit! American Legion Post 168 – 803 Emma St. Tickets Here
11 PM— Decades of Divas 80’s Prom Afterparty @ the Birdcage Cabaret – 504 Angela. There’s no need to change, just join us after the Decades of Divas 80’s Prom for the perfect way to cap off an incredible evening!

Sunday, September 6

Noon pm —“You CAN Sit With Us” Drag Brunch: We are excited to announce that we will be adding 25 more seats at the bar! **Please note that these seats are located in a separate area and may have limited visibility. Performers will be walking through the entire space to be sure you are part of the show, but your view will be obstructed. The price for these seats will be slightly lower at $40. Hosted and produced by Beatrix Dixie. Join us for a fabulous Drag Brunch from 12–3 PM, with dazzling performances including drag kings! Enjoy a vibrant afternoon of entertainment, laughter, and a delicious buffet featuring shrimp bisque, French toast with berries, eggs, bacon, sausage, home fries, cured salmon, benedicts, jerk chicken with yellow rice, croissants, fresh fruit, salad, and sweet treats like flan and key lime pie. Ticket link is HERE! You can also reserve your spot and purchase your tickets by contacting Fritzie at (305) 294-4603 or Fritzie@gaykeywestfl.com. Key West Cooking School & Bar – 291 Front Street (inside The Shops of Mallory Square up the escalator).
This event is All Welcome and 21+.
3 pm — Hot Dog Church. If you’re looking for a laid-back atmosphere to break from all the partying you did all week, then this is the place for you! Yes, there will be hot dogs, there will be games, there will be chill vibes!
4 pm — The Original Tea Dance – a Key West Tradition. Join us for the last dance to close out Womenfest 2025 @La Te Da featuring DJ Rude Girl.

Daily Activities

Museums: Key West Art & Historical Society, Ernest Hemingway, Key West Butterfly Conservatory, Little White House, Key West Aquarium, Mel Fisher Maritime Museum, Key West Firehouse Museum, Key West Light House, Key West Ship Wreck Museum, Audubon House, Oldest House and Garden Museum, USCGC Ingham Museum, Tennessee Williams Exhibit.
Land Activities: Key West Food Tours, Key West Cooking School, Fort Zachary State Park, West Martello Tower, Key West Tropical Forest and Botanical Garden, Key West Cemetery, Key West Adventures, Papa’s Pilar Rum Distillery, Ghost Hunt, Old Town Trolley Tours, Conch Tour Train, Haunted Key West, Ghosts and Mysteries, Ghosts and Gravestones, D’vine Wine Gallery.
Water Activities: Blu Q, Classic Harbor Lines, Cruisin’ Tikis, Danger Charters, Fish N Chicks, Fury, Island Vibe Charters, Java Cat, Jolly Rover II, Key West Eco Tours, Key West Sailing Center, Key West Snorkeling. Land Boat Charters, Off the Charts, Schooner America, Sunset Sail Key West, Sunset Watersports, SV Argo Navis, Yankee Freedom.

BOOK YOUR VACATION RENTAL FOR KEY WEST WOMENFEST
Don’t wait to book your Key West vacation rental if you’re planning on attending Key West Womenfest. Choose from our selection of luxury homes, vacation rentals with a pool, pet friendly rentals, condos or townhomes.
Browse Vacation Rentals>>>

Just a Few Friends - Key West
2026-09-03 - 2026-09-07 | Key West, Florida, Key West, FL, 33040, United States
2026 JAFF SCHEDULE Preliminary schedule — subject to change
All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)
Full schedule & tickets on sale May 1

April 28 for package holders
April 30 for badge holders

WEDNESDAY, SEPTEMBER 2
11:00 AM — JAFF Headquarters | Key West First Legal Rum
12:30 PM — A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show | Comedy Key West
6:00 PM — Early Welcome Party at the Chart Room | Pier House

THURSDAY, SEPTEMBER 3
9:30 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound
11:00 AM — Cooking Show: Grits n Grunts | Key West Cooking Show
11:00 AM — Friends of Bubba HQ | Key West First Legal Rum
12:30 PM — A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show | Comedy Key West
1:00 PM — Chart Room Daily Hangout Headquarters | Pier House
1:00 PM — Truman Waterfront Farmers Market | Truman Waterfront Park
2:15 PM — Tales from the Chartroom | Pier House
5:00 PM — Cheeseburger Beach Battle and Tribute Concert | Southernmost on the Beach
7:00 PM — “Open Mic / No Mic Night” at Andy’s Cabana | Andy’s Cabana
8:00 PM — After Party | TBD

FRIDAY, SEPTEMBER 4
8:00 AM — Plogging the Keys Waterfront Cleanup | Reef Relief @ the Historic Seaport
8:00 AM — Painting Paradise: A Guided Plein Air Experience (Session 1) | Shrimp Boat Sound
9:00 AM — Island Time Brunch Buffett | TBD
11:00 AM — Key West’s Favorite Son City Proclamation | Shrimp Boat Sound
11:00 AM — Cliff Cody Performance at Proclamation | Shrimp Boat Sound
11:00 AM — Friends of Bubba HQ | Key West First Legal Rum
12:00 PM — Coconut Telegraph Trolley Tour | Pier House
12:30 PM — A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show | Comedy Key West
1:00 PM — Chart Room Daily Hangout Headquarters | Pier House
1:00 PM — Screening with Panel Discussion | Tropic or San Carlos
2:30 PM — VIP Special Edition: Jimmy Buffett Tribute Show | Comedy Key West
3:45 PM — Tales from the Chartroom | Pier House
5:00 PM — Duval Street Party with the Landshark Band | TBD
9:00 PM — Outdoor Movie | Southernmost Pint Brewpub

SATURDAY, SEPTEMBER 5
9:00 AM — Painting Paradise: A Guided Plein Air Experience (Session 2) | Louis Backyard
10:00 AM — Private Distillery Tour with Paul Menta | Key West Legal Rum
10:00 AM — Coconut Telegraph Trolley Tour | Pier House
10:00 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound
10:00 AM — Sails Up: Intro to Sailing Experience | Key West Sailing Center
11:00 AM — Ultimate Friend’s Private Distillery Tour with Paul Menta | Key West Legal Rum
11:00 AM — Best Friend’s VIP Live Music Sail | Fury Water Adventures
11:00 AM — Author/Photographer Book Signing | Books & Books @ Studios of KW
11:00 AM — Friends of Bubba HQ | Key West First Legal Rum
11:00 AM — Back to the Island Beach Party | Bourbon Street Pub
12:30 PM — A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show | Comedy Key West
1:00 PM — Chart Room Daily Hangout Headquarters | Pier House
1:15 PM — Tales from the Chartroom | Pier House
2:00 PM — Milagro Margarita Historic Seaport Bar Stroll | The Marker Resort
2:00 PM — Milagro Margarita Duval Street Bar Stroll | La Concha
5:00 PM — Early Access: Table Seating (JFF VIPs) | Big Stage
5:30 PM — Early Access: Entry (JFF Badge Holders) | Big Stage
6:00 PM — Doors Open (GA) | Big Stage
6:30 PM — Mike Stack & Friends | Big Stage
6:30 PM — Cruisin’ Tiki Sunset & Music Cruise | Cruisin’ Tikis @ Mac’s Place
6:30 PM — Latitude Adjustment Sunset Sail | The Dock @ Sunset Pier
8:00 PM — Changes in Latitudes: Concert ft. the Wheeland Brothers | Sunset Pier
8:00 PM — Outdoor Movie | Southernmost Pint Brewpub

SUNDAY, SEPTEMBER 6
10:00 AM — Coconut Telegraph Trolley Tour | Pier House
10:00 AM — Bubbles Brunch Sail | The Dock @ Sunset Pier
11:00 AM — Book Signing | Books & Books @ Studios of KW
11:00 AM — JAFF Headquarters | Key West First Legal Rum
12:00 PM — Wheeland Brothers Poolside Acoustic | Ocean Key Resort
12:30 PM — A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show | Comedy Key West
1:00 PM — Chart Room Daily Hangout Headquarters | Pier House
1:00 PM — Best Friend VIP Private Show | Margaritaville Restaurant
1:00 PM — Pool Party at the Marker | The Marker Resort
1:15 PM — Tales from the Chartroom | Pier House
5:00 PM — Second Line Memorial Walking Parade | 100 Duval Street
6:00 PM — Key West Artisan Market at the Party in the Park | Truman Waterfront Park
6:00 PM — Party in the Park: Tribute to Bubba | Truman Waterfront Park

MONDAY, SEPTEMBER 7
10:00 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound
10:00 AM — Tin Cup Sailing Adventure | Danger Charters
11:00 AM — JAFF Headquarters | Key West First Legal Rum
12:30 PM — A Pirate Looks Back, the Key West Jimmy Buffett Tribute Show | Comedy Key West
1:00 PM — Chart Room Daily Hangout Headquarters | Pier House
2:00 PM — Tales from the Chartroom | Pier House
2:30 PM — Pencil Thin Mustache Contest | Chart Room
5:00 PM — Early Access: Table Seating (JFF VIPs) | Sunset Pier
5:30 PM — Early Access: Entry (JFF Badge Holders) | Sunset Pier
6:00 PM — Doors Open (GA) | Sunset Pier
6:30 PM — Come Monday: Cayman & the Mango Men | Sunset Pier
6:30 PM — Island Tiki Sunset & Music Cruise | Cruisin’ Tikis @ Mac’s Place
8:30 PM — Last Call | TBD

Key West Fantasy Fest!
2026-10-16 - 2026-10-25
October 16 – 25, 2026
2026 Theme: Musical Icons & Iconic Musicals

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!
Fantasy Fest 2026 Daily Events Guide
A day-by-day guide to what’s happening around Key West during Fantasy Fest for guests planning their stay with Historic Hideaways.
All information / data courtesy of the event organizers website. Please visit their link for tickets and updates where applicable. (Information subject to changes, errors, and omissions.)

Daily Diversions

Your Picture with the King & Queen Sculpture
FreeOpen Daily 9AM–5PM510 Greene Street
Stop by the Chamber of Commerce and snap a selfie with the Fantasy Fest King & Queen Sculpture, then pick up official Fantasy Fest swag. Tag #Keywestchamber and #fantasyfest for a chance to win prizes.

801 Cabaret — Sushi & The 801 Girls
21+Oct 17–23 & 26 · 9PM & 11PM801 Duval Street
The longest-running drag show in Key West. Valid photo ID required, guests must be 21+. Reservations strongly suggested; no shows Oct 24 & 25. Doors at 8PM.

Body Art & Sunsets at Sunset Pier
From $60Oct 17–25 · Starts 1PM0 Duval Street, Sunset Pier
Femme Fatale Body Art’s all-female team offers body art from small pieces to full-body work, with waterproof/sweat-proof options, plus music, food, and sunset views. Book directly by texting team lead Amanda at 850-596-4065.

Fantasy Facade — sponsored by Haunted Key West
Free to enterRegister by Mon Oct 13 · Judged Mon Oct 20
A Halloween decorating contest open to all Key West and Stock Island businesses and residents. $1,000 grand prize for Best Spooktacular Showstopper, plus awards for Creepiest Concept, Bloodiest Horror Scene, Best Fantasy Fest Theme Integration, and the Great Pumpkin Award. Entries appear on the official Fantasy Fest app map.

Fury Water Adventures Discount
Valid Oct 16–31
Save 10% on all Fury trips and 15% on rentals with promo code FANTASY, booked online or at any authorized Fury sales booth. One coupon per group; blackouts and restrictions may apply.

Happy Hour at Orchid Key Inn Bar
Bar open daily 12PM–10PMHappy Hour 5–7PM
Intimate poolside bar with a boutique wine list, mixologist-crafted cocktails, and house-made infusions with fresh-squeezed juices.

IVs in the Keys
Call 305-395-8245
Key West’s original medical spa offers mobile hydration IV service. Fantasy Fest special: mobile service fee waived for groups of 5+, with an additional 10% off for groups of 10+.

Karaoke Party
Nightly 8PM–2AM618 Duval St, Key West Empourium
Nightly karaoke throughout Fantasy Fest week at the Karaoke Lounge, hosted by Stars Karaoke Club and DJ Rico.

Photo Op: Fest Letters All Day
FreeOpen daily from 11:30AM631 Greene Street
Snap a selfie with the giant Fantasy Fest letters at Conch Republic Seafood Company. Happy hour daily 4–7PM in the bar & patio.

Pot Stop Selfie Contest
21+Greeen House locations
Grab props and snap a selfie in-store for a chance at a grand prize valued over $500. Key West locations at 211 Duval St, 532 Duval St, and 431 Front St, plus “The Mothership” at 3128 N Roosevelt.

Sloppy Joe’s Hangover Headquarters
Daily from 9AM · Kitchen opens 10AM201 Duval Street
Morning-after recovery all week long with Deep Eddy Vodka cocktails, Bloody Marys, Dulce Vida frozen margaritas, live entertainment, and giveaways.

16

Friday · October 16
Kickoff Weekend

Bahama Village Goombay Festival
FreeFamily-FriendlyNoon–MidnightPetronia & Emma St
A street party in the historic Bahama Village neighborhood with island arts, crafts, food, and nonstop music ranging from reggae to soca.

Barbie’s Pink Pool Party for Breast Cancer Awareness
$20 donation4–7PMThe Marker Key West Harbor Resort
Barbie/Ken pink costume party benefiting Womankind Key West, with music from DJ Maya and DJ Top Jimmy, a costume contest, photo booth, and pink drink & food specials.

Happily Fur-Ever After Royal Coronation
Free general admissionDoors 6PM · Show 7PMCoffee Butler Amphitheater, 21 Quay Rd
Florida Keys SPCA event crowning the King and Queen of Fantasy Fest after a 6-week fundraising campaign, with a tribute to King Christopher Elwell. Ticketed packages include reserved seating and a 3-course dinner; general admission lawn seating is free. Contact Jennifer@fkspca.org for info.

The Dave Matthews Tribute Band
Free7PMSunset Pier
A 5-piece tribute band bringing the energy and intimacy of a live Dave Matthews Band show to Sunset Pier.

17

Saturday · October 17

Bahama Village Goombay Festival
FreeFamily-FriendlyNoon–MidnightPetronia & Emma St
Continues from Friday — island arts, crafts, food, and live music at the corner of Petronia and Emma Street.

Rum with Bum
Free admission10AM–2PMAlex Vega Key West Firehouse Museum, 1024 Grinnell St
A local-history photo op referencing former Key West Fire Chief Joseph “Bum” Farto, who disappeared in 1976. Snap a photo and receive a rum shot; donations appreciated.

Mermaid Mayhem at the Blue Flamingo Resort
12–4PM3820 N Roosevelt Blvd
An official Fantasy Fest undersea-themed pool party at the new Blue Flamingo Resort.

Witches in the Hammock at Crane Point
$15 adults / $5 kidsFamily-Friendly6:30–9PMCrane Point Hammock, Marathon — 5550 Overseas Hwy
Lantern walk through the hammock, fire-pit dancing “witches,” a hayride, games, a Halloween movie screening, and concessions including popcorn, cider, corn dogs, and roasted corn.

That Arena Rock Show
Free7PMSunset Pier
A high-energy tribute concert to classic ’70s and ’80s rock at Sunset Pier.

18

Sunday · October 18

Key West Artisan Market at Higgs Beach
Free admission10AM–2PM1707 White Street
Fantasy Fest edition of the Artisan Market with fine crafts and art from Florida Keys makers, official Fantasy Fest merch, international food trucks, and live music.

Medusa’s Forbidden Lagoon
12–4PMMargaritaville Beach House, 2001 S Roosevelt Blvd
A poolside party with a mythical/serpent theme — DJ, food, and drinks, with jewel-tone and metallic dress encouraged.

That Arena Rock Show
Free7–9PMSunset Pier
Repeat performance of the classic rock tribute show at Sunset Pier.

19

Monday · October 19

Havana Cabana’s Duck, Duck, Booze Pool Party
Free12–4PM3420 N Roosevelt Blvd · 305-294-5541
A rubber-duck-themed pool party with beverage samples, swag, and a chance to win a $200 gift card plus other giveaways from The Tazzle.

Margs & Makers
12–5PMSacred Space Gallery, 529 Southard St
Margaritas and a pop-up shop featuring 30 women artists at this all-female gallery.

Mrs. Roper Romp
Free (donations to charity)5PM0 Duval Street, Sunset Pier
A “Three’s Company”-themed party with sunset views, music, trivia, games, and specialty drinks. Not ticketed, but donations go entirely to a local charity. Info: 850-596-4065.

A Green Parrot Beatles Tribute
Free5:30, 9:00 & 11:00PM601 Whitehead Street
Key West’s own Beatle Band performs three sets, with an optional ’60s dress-up theme for the crowd.

Fantasy Fest 5K Run/Walk
6PM startTiki House Key West, Duval Street
“Bed-Time Stories and Magical Monsters”-themed 5K down Duval Street with a themed shot stop at Hard Rock Cafe, plus a “Tipsy Fairy Mile” walking option and a post-race party at Tiki House. Registration required.

Masquarade Monday Wine Dinner presented by Bogle Wines
$150 (dinner & wine, gratuity extra)Doors 6PM · Dinner 7PMA&B Lobster House, 700 Front St
Regency-era masquerade ball and multi-course wine dinner with live music. Masks required; reserve seats at Keystix.com.

Martini Monday at Virgilio’s
$7 martinis6PM–close524 Duval St
$7 martinis all night, plus live music and food.

Femme Fantasy Fete: Vixens & Villains
21+, Women-Only$25 / $45 VIP9PM–untilMangoes, 700 Duval St
A dark-fairytale-themed women-only evening with cocktails, a costume contest, VIP lounge access, mask-making, and a photo booth.

Kinky Carnival
Adult content, cash only$75Open bar 8–11PM · Party until 1AMFirst Flight, 301 Whitehead St
Key West’s original Fantasy Fest kink party, in its 28th year, with interactive BDSM stations and fetish rooms. Kinky costume required for entry; cash only. Tickets sold Oct 17–20.

Sloppy Joe’s Comic Book Cape-ers Party
Live music from 10AM201 Duval Street
Themed costume party at Sloppy Joe’s with live entertainment throughout the day and night.

Tops or Bottoms Underwear Party
Adult content, men’s event10PM–4AMNew Orleans House, 724 Duval St · 305-293-9800
Private underwear party with free clothes check.

20

Tuesday · October 20
Tutu Tuesday

Dante’s 4th of July Party
$10 cover11AM–5PM951 Caroline St · 305-293-5123
Patriotic-themed pool party with food and drink specials.

Rum Revelation, A Cocktail Journey ft. Captain Morgan
$99 ppClasses at 12 & 2PMKey West Cooking Show, 291 Front St, Ste 207
Rum tasting and cocktail-making class featuring Captain Morgan White and Spiced, with two cocktails made and a swag bag included.

Storybook Splash Pool Party at Winslow’s Bungalows
12–4PM725 Truman Avenue
Storybook-character costume pool party with two pools, live entertainment, food/drink specials, a costume contest, and hourly vacation raffles.

Florida Keys Council of the Arts Poster Signing Party
Free3–5PMLa Concha Hotel, 430 Duval Street
Meet the winning 2026 poster designer, get posters/shirts/swag, and sample wine courtesy of Bogle Wines.

Tutu Tuesday Pre-Party Bar Crawl
Steps off 6PMMary Ellen’s, 420 Applerouth Lane
A walking parade pre-party with a drink stop, feeding into the main Tutu Tuesday event; parade pass includes entry to the Tutu Party.

Fantasy Fest Spooky Trivia
Sold Out6PMSouthernmost Beach Resort, 1319 Duval St
Six-round Halloween-themed trivia night; costumed players get bonus points. This one is already sold out per the listing.

Tutu Tuesday: Tuesday Night Fever & Our Silly Robot Friends
$30 advance / $40 day-ofDoors 6PM — no tutu, no entryCaroline St district (4 venues)
15th annual dance-party crawl across four venues (First Flight Brewery, Hanks Hair of the Dog Saloon, The Alamo, and General Horseplay as the hub) with 10+ DJs on one wristband. VIP adds treetop lounge access, limited to first 150.

Tay Tay Tuesday: In Your Wildest Dreams
Free6–9PMSunset Pier
Live Taylor Swift tribute concert performed by local artist Meghan Barter.

Tutu Salsa Sessions
Free7–9PMSouthernmost Beach Café, 1319 Duval St
Salsa dance instruction while wearing tutus, sponsored by Dulce Vida Organic Tequila, with margarita and sangria specials.

Cocktails for Animal Tails, presented by Dirty Monkey
$408–11PM (early entry 7:30PM with pre-sale)Rick’s Bar, 202 Duval St
Charity event benefiting the Florida Keys SPCA with unlimited drinks across the Rick’s complex and an animal-costume contest with a $500 grand prize. Contact Jennifer at 305-294-4857 ext. 5.

Capt. Tony’s Party in Plaid
Free8PM428 Greene St · 305-294-1838
Plaid-costume party with music and drinks at Capt. Tony’s.

21

Wednesday · October 21

Sloppy Joe’s Slumber Party
Live music from 10AM · Contest signup 8:15PM201 Duval Street
Sleepwear-costume contest themed to “Bedtime Stories & Magical Monsters.” Prizes: $500 / $250 / $100 Sloppy Joe’s gift cards; band “Nightbreakers” plays after the contest.

Swayzees Pajama Pool Party
Free2–5PMSoMo’s Shores Pool
Pajama or swimwear pool party with live music from Les Greene and the Swayzees, sponsored by Empress Gin.

Bowties & Birthday Suits
21+, adult content, gay men’s event$50 cash/credit5–8PM (resort access thru Thu 4AM)Island House, 1129 Fleming St
Clothing-optional pool party at Island House resort; no costumes needed. Admission includes locker, towels, and extended resort access. Photo ID required.

Monsters Under the Sea Costume Contest
$25 + $5 charity donation7PM–MidnightMargaritaville Cafe, 500 Duval St
Underwater-monster costume contest. 1st place $1,000, 2nd place a PlayStation 5, plus hotel stays and sunset cruises as additional prizes. Entry includes a drink and appetizer.

The 4th Annual Party Like a Rockstar
6PM–Midnight (Guitar Shred-Off at 8PM)618 Duval St, Key West Empourium
Guitar Shred-Off competition ($1,000 cash prize), a live-band set from 9–10PM, then a Costume & Air Guitar Contest at 10PM ($300/$200/$100 prizes). Partial proceeds support a local musician’s medical bills.

The Bedtime Bizarre at the Blue Flamingo Resort
6–10PM3820 N Roosevelt Blvd
“Bedtime Stories & Magical Monsters”-themed evening event with lounges, cocktails, live entertainment, and immersive décor. Pajama-chic to fully costumed attire encouraged.

Pet Masquerade
$25/entry to compete · free to watchRegistration 5PM · Show 6:30PMKey West Amphitheater, Truman Waterfront Park, 21 E Quay Rd
Pet costume contest with four categories (Junior, Pet/Owner Lookalike, Most Exotic, Best Theme Adaptation) plus Best in Show. Proceeds benefit the Monroe County Sheriff’s Office Animal Farm. Bring a blanket or lawn chair.

Studio 69 Disco Party
$15 / $45 open bar / $75 open bar + dinner7PM till late (open bar 7–9PM)The Alamo, 4 Charles St
’70s disco-themed dance party with local DJs Scott Gerke and Chris Cohen.

Wharfstock at the Schooner Wharf Bar
No cover7PM–midnight202 William St · 305-292-9520
1960s Woodstock-themed sit-in with live music from “That Hippie Band,” costume prizes for sexiest hippie chick and grooviest dude (judged 8:30PM).

LUV2GLOW: Liquid Frequency
21+$30–$40 GA / $100 VIP8PM–4AMRick’s Upstairs
14th annual UV blacklight glow party with multiple DJs and a Funktion-One sound system. No glow, no entry — come dressed or painted to glow under blacklight. Door price increases night-of (cash only).

Desire Male Fetish Party
Adult content, men’s event10PM–4AMNew Orleans House, 724 Duval St · 305-293-9800
Private fetish party with fetish attire encouraged and free clothes check.

22

Thursday · October 22

Berkshire Hathaway Parade of Homes Mega Open House
Free11AM–3PMKey Largo to Key West
Keys-wide open house event; visiting homes enters guests for VIP tickets to a Fantasy Fest Parade viewing party (bonus entry for 3+ open houses visited). Note: source text lists this under “Thursday, October 23rd” — confirm actual date.

Southernmost Scavenger Hunt’s 6th Annual Bar Crawl
$45 ppCheck-in 2PM · Crawl 2:30–4:30PM
Team bar crawl (teams up to 6, 21+) sponsored by Dulce Vida Organic Tequila. Includes a free drink, swag, souvenir cup, and scavenger hunt map. Awards announced 5PM. Note: source text references “October 26th” — this event also recurs on Oct 24; confirm the correct date.

Les Greene & The Swayzees Pajama Pool Party (Take 2)
Free2–5PMThe Marker Resort
Second round of the pajama/swimwear pool party with live music, sponsored by Dulce Vida Organic Tequila.

Dante’s 19th Annual Halos & Horns Pool Party
$25 (benefits Autism Society of the Florida Keys)Doors 11AM · Party noon–6PM951 Caroline St · 305-293-5123
Angel/devil-themed pool party with cash prizes, free body painting, live music, and a stage in the center of the pool; pole dancing starts 4:30PM.

Funk It Up Party
Free to watch5:30, 9:30 & 11PMGreen Parrot Bar, 601 Whitehead St
Live sets from funk band Funk You, blending modern and vintage dance grooves.

Studio 430 Dance Club Under the Stars
DJ 6–10PMLa Concha Hotel & Spa, 430 Duval Street
Rooftop pool-deck lounge party with classic cocktails and DJ sets.

42nd Annual Headdress Ball
$30 GA – $320 premium tableDoors 6:30PM · Show 8PMCoffee Butler Amphitheater, Truman Waterfront Park
The Key West Business Guild’s flagship LGBTQ+ event, judged headdress competition with a $5,000 top prize, emceed by Randy Roberts. Sells out most years — book early via keystix.com or gaykeywestfl.com/headdress-ball. Note: source text says “Thursday, October 23, 2025” — confirm current-year date.

5th Annual Rock the Tatas Contest
$25 (benefits Making Strides Against Breast Cancer)Doors 5PM · Contest 7PMHanks Hair of the Dog Saloon, 409 Caroline St
Breast cancer awareness costume/charisma contest with a $500 first prize plus crown and sash, live music from 9PM.

Cowboys, Cowgirls, & Monsters
$15 / $45 open bar / $75 open bar + dinner7PM till late (open bar 7–9PM)The Alamo, 4 Charles St
Western/monster costume party with local DJs Scott Gerke and Chris Cohen and late-night food.

Fat Tuesday Pink Party
8PM–close305 Duval Street
Pink-costume party with live entertainment and a costume contest ($500/$250/$100 bar tabs). Note: source text says “Thursday 10/23” — confirm date.

Sloppy Joe’s 46th Annual Toga Party
Live music from 10AM · Contest signup 8:15PM201 Duval Street
Long-running toga-costume contest, individual or groups of 2–4. Prizes $500/$250/$100 Sloppy Joe’s gift cards; “Nightbreakers” plays after.

Exposed at the Bourbon St. Pub
Adult content, open to all$100 presale / $110 day-ofDoors 9PM · 10PM–4AM724 Duval Street
Poolside foam party with two dance floors, blacklight room, and exotic dancers. Full access to the pool area with limited free towels and clothes check. Tickets via New Orleans House or Keystix.com.

Irish Kevin’s Annual 80’s Party
No coverLive music open to close · Band at 10PM211 Duval St · 305-292-1262
’80s-themed party with a dedicated cover band taking the stage at 10PM.

23

Friday · October 23
Street Fair Begins

Fantasy Fest Street Fair & Costume Promenade
Free to attendArts & Crafts noon–10PM · Food noon–1AMDuval Street
Duval Street’s signature mile-long street fair: arts, crafts, and food on Friday, with Saturday shifting focus to food served late into the night.

Bourbon St. Pub’s Afternoon Pool Party
Cover charge (free clothes check)Noon–~5PMNew Orleans House, 724 Duval St · 305-293-9800
Poolside dance party / street fair T-Dance with live DJs, drag queens, and games.

Southernmost Playboy House — Beach Bunny Pool Party Bash
Adults only$30Noon–5PM1400 Duval Street · 305-296-3141
Oceanfront infinity-pool party with DJ Hazard and drink specials; bunny ears required for topless sunbathing per venue policy.

Comparsa at the San Carlos Street Party
Free entryNoon–Midnight516 Duval St · 305-294-3887
Cuban music and dancing street party hosted by the San Carlos Institute, with a mojito bar.

Captain Morgan’s Masquerade March (The Locals’ Parade)
FreeBlock party 4PM · Steps off 5:30PMFrances & Petronia St
A locals-focused costume parade tradition through Old Town into the Street Fair, with a red-carpet block party, 360-selfie station, and complimentary drinks along the route.

The 4th Annual Captain Morgan’s Pirate Party
No cover6:30–10PM (bar until 1AM)618 Duval St, Key West Empourium
Pirate-themed party with nautical music and a costume contest paying $500/$300/$200.

Surf’s Up at the Hog’s Breath Saloon
Free7PM400 Front Street · 305-296-4222
Surfer-costume party with live music and drink specials.

25th Annual Living Art Expo
FreeParty 7PM · Contest 8PMSunset Pier
Body-painting/living-art competition for solo, male, female, or group entries, competing for $2,000 in cash and prizes ($1,000 for Best Overall). Registration via Sunset Pier, 305-295-7047.

Aquaplex Slay Queen — Chapter 3, Part 1: Nightmare on Duval St.
$35 / $200 booth8PM711 Duval St
Horror-themed drag show from Beatrix Dixie and Jonathan Barrett featuring the Aquanettes. Reservations recommended — tends to sell out. Note: source text says “Friday October 24th” — confirm date.

Kinky Couples Party hosted by RubberDoll
Couples only, adult content$275–$500Shows 8PM & 11PM801 Bourbon Bar, 801 Duval St
Couples-exclusive event with a performance from latex entertainer RubberDoll. Pre-registration required; no re-entry once you leave. Repeats Saturday.

Midnight Mass: A Heated Gaythering
Adult content, gay men’s event$60 cash/credit10PM–2AM (resort access thru Sat 4AM)Island House, 1129 Fleming St
Adults-only late-night event at Island House resort. Admission includes first drink, locker, towels, and extended resort access. Photo ID required.

PlexXx
Adult content$25 cover10PM504 Angela St
Late-night dance party at the Birdcage Cabaret hosted by Holly Dae, featuring an international DJ.

24

Saturday · October 24
Parade Day

Fantasy Tennis Tournament
$75 donation8–11:30AMHiggs Beach Tennis Courts
Ladder-format charity tennis tournament benefiting Keys to Be the Change mentoring programs; includes breakfast, drinks, awards, and lunch. Registration limited to 20 — contact 541-974-4398 or heidi_golightly@yahoo.com. Note: source text says “Saturday, October 25th” — confirm date.

Fantasy Fest Street Fair & Costume Promenade
Free to attendNoon till early hoursDuval Street
Saturday’s Street Fair shifts focus to food, running late into the night alongside the parade.

Comparsa at the San Carlos Street Party
Free entryNoon–Midnight516 Duval St · 305-294-3887
Cuban music, dancing, and a mojito bar hosted by the San Carlos Institute.

New Orleans House Pool Party
Clothing optionalCover charge (free clothes check)Noon–5PM724 Duval St · 305-293-9800
Parade-day pool party with live DJ and pool games.

Southernmost Scavenger Hunt’s 6th Annual Bar Crawl
$45 ppCheck-in 2PM · Crawl 2:30–4:30PM
Team bar crawl (teams up to 6, 21+) sponsored by Dulce Vida Organic Tequila — same event as listed under Thursday Oct 22; confirm which date is correct before publishing.

Bourbon St. Pub’s VIP Balcony Bash
$200 VIP presale, 150 availableDoors 6PM · 7–10PMNew Orleans House, 724 Duval St
Grand-balcony parade viewing with open bar and catered buffet, private entrance and restrooms. Tickets from 305-293-9800 or keystix.com.

First Flight Parade Viewing Party
$125–$150++Check-in 5:30PM · 6–9PMFirst Flight Island Restaurant & Brewery
Dinner buffet and 3-hour open bar with a choice of sidewalk chair, indoor table, or porch-chair seating for the parade.

Mangoes Fantasy Fest Parade Party
$80 presale / $100 day-ofDoors 6PM · Parade 7PMMangoes, 700 Duval St
Elevated patio parade-viewing with drink specials, a special dinner menu, and live piano from Dave Bootle after the parade.

Nightcaps & Nightgowns: A Moonlight Pajama Viewing Party
$250–$350Seating begins 6PMHellings Curry Museum
Reserved-seating parade viewing with hors d’oeuvres, desserts, and two complimentary drinks at Eleanor’s Elixirs Martini Bar. Pajama-themed costumes encouraged; sells out most years.

Viva’s Grand Finale Viewing & Dinner Parade Party
$90 / $135 (open bar 6–9PM)6PM (check-in 5:30PM)Viva Argentinian Steakhouse, 903 Duval St
Outdoor tiki bar and air-conditioned indoor viewing, live music and DJ, plus a live 8-piece Argentine band after the parade.

Deep Eddy Vodka Fantasy Fest Parade
FreeSteps off 7PMDuval Street
The main event — floats, costumes, and dance groups down Duval Street in front of a crowd historically numbering in the tens of thousands.

Parade Viewing Party at La Te Da
6–10PM1125 Duval Street
Street-side parade viewing emceed by WEOW’s Rude Girl.

Aquaplex Slay Queen — Chapter 3, Part 2: Dreamcatcher
$35 / $200 booth10PM711 Duval St
Whimsical mythical-creatures-themed drag show, second half of the two-night Slay Queen event. Reservations recommended.

Kinky Couples Party hosted by RubberDoll
Couples only, adult content$275–$500Shows 8PM & 11PM801 Bourbon Bar, 801 Duval St
Second night of the couples-only latex/fetish-themed event with RubberDoll.

The Blue Party at the Backyard Bar
8PM onward618 Duval St, Key West Empourium
Ocean/mermaid-themed party with Jeff Clark’s All Star Band; partial proceeds support Sea Basecamp.

25

Sunday · October 25
Wind Down

Fantasy Pickleball Tournament
$100 donation8–11:30AMHiggs Beach Pickleball Courts
Charity pickleball tournament for Keys to Be the Change, including breakfast, a hat/visor, awards, and lunch. Limited to 40 registrants — 541-974-4398 or heidi_golightly@yahoo.com. Note: source text says “Sunday, October 26th” — confirm date.

Children’s Day
Family eventNoon–5PMBayview Park, Truman Ave & Eisenhower Dr · 305-292-8912
Family-friendly festival with food, rides, games, arts and crafts, and a kids’ costume contest.

After Church Pool Party
Adult content, gay men’s event$50 cash/credit12–4PM (resort access thru Mon 4AM)Island House, 1129 Fleming St
Clothing-optional pool party with a Sunday raffle. Admission includes locker and towels. Photo ID required.

Hangover Pool Party at SoMo’s Pineapple Pool
Free1–4PMSouthernmost Beach Resort
Recovery-day pool party with food/drink specials and a live DJ. Note: source text says “Sunday, 10/26” — confirm date.

“The Fat Lady Sings” Tea Dance
$54–8PMLa Te Da, 1125 Duval St · 305-296-6706
Traditionally the last official event of Fantasy Fest week, with music from DJ Rude Girl.

Reggae Lou & The Kind Budz Rehab Pool Party
Free12–5PMThe Marker Resort, 200 William St
Sponsored by Dirty Monkey Banana Peanut Butter Whiskey — live reggae music, drink specials, and two pools.

28

Wednesday · October 28
Post-Fest Bonus

Golf Cart Facade Viewing Tour
6:30–9PMGreeen House Mothership, 3128 N Roosevelt Blvd
Post-Fantasy-Fest, pre-Halloween golf cart tour of decorated houses and businesses entered in the Facade Contest. Costumes and a golf cart decor contest encouraged; use code FANTASY for 15% off Fury golf cart rentals. Designate a sober driver.

Key West Headdress Ball
2026-10-22 | Truman Waterfront Park, Key West, FL, United States
Key West Headdress Ball

The Key West Business Guild proudly presents the 43rd Anniversary Edition of the Headdress Ball — one of the most anticipated events of the Fantasy Fest Celebration, on Thursday, October 22, 2026, at the Coffee Butler Amphitheater at Truman Waterfront Park. Doors open at 6:30 PM, with the show beginning at 8:00 PM.

This unforgettable evening of creativity, glamour, and entertainment will once again be hosted by legendary Key West entertainer Randy Roberts, with music by WEOW’s RudeGirl. Guests will experience an extraordinary showcase as twelve to fifteen contestants unveil their stunning Headdress creations, judged from the shoulders up, all competing for the coveted $5,000 grand prize.
The evening will also feature performances by some of Key West’s most celebrated local talent, making this a true highlight of Fantasy Fest. Guests can enjoy full bar service, specialty wines, and the convenience of preordered food delivered directly to their tables.
Ticket options: (does not include fees)
• Premium Table for 4 — $400( includes a bottle of wine of your choice, non-alcoholic drink option, or bucket of beer)
• VIP Table for 4 — $290
• Chair Seating — $40
• General Admission (Grass Seating) — $30

The Headdress Ball continues to celebrate the vibrant spirit, creativity, and welcoming atmosphere that makes Key West one of the world’s most unique destinations for visitors from all walks of life.

For more information, or to enter the Headdress Contest, visit gaykeywestfl.com/headdress-ball or call 305-294-4603.
This event always sells out, so book your tickets early.

Race World Offshore (aka Boat Races!)
2026-11-01 - 2026-11-08 | Truman Waterfront Park, Key West, FL, United States
National Series Event

Key West World Championship
November 1st – 8th, 2026

ADRENALINE & HIGH SPEED Experience

Step into the exhilarating world of Race World Offshore, where the ocean becomes a high-speed battleground for cutting-edge boats and fearless competitors. Welcome to Race World Offshore, where every moment is a celebration of nautical prowess and the relentless pursuit of victory on the offshore racing stage.
____________________________________________

Race World Offshore is excited to bring teams and fans to Key West for an amazing Offshore World Championship experience presented by Performance Boat Center. RWO is the premier Offshore Racing Sanctioning body in the United States and our team is dedicated to producing an unforgettable week. With the most experienced team in all of offshore racing around the world, RWO anticipates another spectacular event with the world’s best offshore race teams in attendance!
Information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

29th Annual Key West Half Marathon & Runfest
2027-01-15 - 2027-01-17 | Key West, Florida, Key West, FL, 33040, United States
Thank you for joining the festivities
for our 29th Anniversary!
Weekend of January 15-17, 2027
Key West offers a multitude of exciting experiences, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure, making it an unforgettable destination.
And let’s not forget the intriguing fact of having 400 bars on an island that’s only 2 x 4 miles—truly a unique aspect of Key West’s charm! Your time on this magical island is sure to be filled with entertainment and discovery. Don’t forget to set aside some extra time to explore all that Key West has to offer.

______________________________

29th Annual Key West Half Marathon & Runfest®

2027 SCHEDULE OF EVENTS

Wednesday, January 13, 2027 (Day 1)

11 am – 1:30 pm – Volunteer Check-In and Party
Location: Sailfish Bar, Half Shell Raw Bar – 231 Margaret Street

Thursday, January 14, 2027 (Day 2)

4:30 pm – 6:00 pm: Runner’s Meet & Greet – Sailfish Bar, Drink Specials
Location: Half Shell Raw Bar

Friday, January 15, 2027 (Day 3)

ALL DAY: ICE PIK Vodka Drink Specials – Frozen Butterfinger Mudslide $15 & Passionfruit ICE PIK Vodka Cocktail $9
Location: Half Shell Raw Bar
2:00 pm – 7:00 pm: Runner’s Expo/Packet Pick-up
Location: Outside the Half Shell Raw Bar
7:15 pm – 10:00 pm Special Late Bib Pick-Up at Fit2Run, 211 Duval Street (BIB’S ONLY. Shirts must be picked up at Runner Expo on Saturday between 1 pm and 6 pm)

Saturday, January 16, 2027 (Day 4 – 5K & 10K)

Breakfast Special: Saluté! On the Beach! 1000 Atlantic Blvd. Will open early with a Three Breakfast Specials and Full Bar!
ALL DAY: Pasta Special – $26.99 – Includes Linguine & White or Red Clam Sauce, Garlic Bread and Side Salad.
Location: Half Shell Raw Bar
ALL DAY: ICE PIK Vodka Drink Specials – Frozen Butterfinger Mudslide $15 & Passionfruit ICE PIK Vodka Cocktail $9
Location: Half Shell Raw Bar
BAG CHECK: 6:00 am – 6:45 am, in front of 1000 Atlantic Ave. – Saluté! On the Beach.
7:00 am: 5K Start and Finish
Location: Higg’s Beach on 1000 Atlantic Blvd.
8:00 am: 10K Start and Finish
Location: Higg’s Beach on 1000 Atlantic Blvd.
8:00 am – 11:00 am: 5K/10K Concert & Awards Party: Featuring Homebred Band – With Reggae Legend & Grammy Winner, Dave Richards
Location: Outside Salute on the Beach, 1000 Atlantic Avenue
9:30 am: All 5K and 10K overall winners will be announced and age group winners will be available for pick up outside Saluté! On the Beach after the 10K at 9:30 am near the start/finish line.
1:00 pm – 6:00 pm: Runner’s Expo/Packet Pick-up
Location: Outside the Half Shell Raw Bar
3:30 pm – Presentation by Dr. Kellee Reed. Introduction to Mike Raymond – Man Kicks Bucket at Bucket List Trip
7:00 pm – 10:00 pm Special Late Bib Pick-Up at Fit2Run, 211 Duval Street (BIB’S ONLY – Shirts must be picked up at Shirt Exchange on Sunday after the race at near Gear Check in the parking lot located in the finish line area)

Sunday, January 17, 2027 (Day 5 – Half Marathon & 8K)

ALL DAY: $8 Bloody Mary and Mimosa Drink Specials
Location: Half Shell Raw Bar
ALL DAY: ICE PIK Vodka Drink Specials – Frozen Butterfinger Mudslide $15 & Passionfruit ICE PIK Vodka Cocktail $9
Location: Half Shell Raw Bar
BAG CHECK: 6:00 am – 6:45 am on Race Day, in the parking lot by the finish line area in front of Waterfront Brewery.
7:00 am: Half Marathon
7:30 am: 8K Start
Location: corner of Caroline Street & Trumbo Road/West Marine (less than two blocks from the Packet Pick-Up location.)
RACE FINISH: Behind Waterfront Brewery.
8:30 am – 12:30 pm: Concert & Awards Party: Featuring The Cayo Ritmo Big Band
Location: Outside Half Shell Raw Bar
9:30 am: 8K Awards at tables near bag check
10:30 am: Half Marathon Awards at tables near bag check
1:00 pm – 5:00 pm The Key West Papa’s Pilar Rum Stroll Sponsored By Papa’s Pilar Rum
Featuring delicious Papa’s Pilar Rum Libation Special at each location!Hemingway Rum Company, Papa’s Pilar Distillery – 201 Simonton Street

Schooner Wharf Bar – 202 William Street
The Marker – 200 William Street
Conch Republic Seafood Company – 631 Greene Street
Ocean Key Sunset Pier – 0 Duval Street
La Concha Tropicado Mojito Bar – 430 Duval Street
First Flight Restaurant – 301 Whitehead Street
RamsHead – 804 Whitehead Street
Southernmost Beach Cafe – 1319 Duval Street

3:00 pm Key West Beach N’ Beer Mile! Outside of the Southern Most Beach Cafe: 1405 Duval St, Key West, FL 33040
4 Loops, 4 Beers, Custom Shirt. Race is NOT TIMED!
Prizes awarded for:
1. Best Team Spirit
2. Best Dressed
3. Least Dressed
4:00 pm – 6:00 pm: Cool Down & Recover Pool Party at the Blue Flamingo Resort. Free Entry! Live Music and Drink Specials. 3820 N Roosevelt Blvd, Key West, FL 33040.
4:00 pm – 6:00 pm: Key West Farewell Party
Location: Salty Oyster with Live Entertainment at the Perry Hotel located 7001 Shrimp Road, Key West, FL 33040. Happy Hour pricing is 50% off well drinks and draft beers. And continue on to Matt’s Stock Island Happy Hour also at the Perry Hotel!!!

Monday, January 18, 2027 (Day 6)

4:00 – 6:00 pm: Marathon Farewell Party and Happy Hour at the Blu Bistro at the Skipjack Resort in Marathon. 20% off all Menu items and Drinks All Day! Just mention you participate d in the Key west Half Marathon
Location: SKIPJACK RESORT & MARINA – 19 Sombrero Blvd, Marathon, FL 33050

All information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Key West Food and Wine Festival
2027-01-27 - 2027-01-31 | Key West, Florida, Key West, FL, 33040, United States
2027 Key West Food and Wine Festival
1/27/26 – 1/31/27
5 continents~5 wines~5 stories~5 Dishes~5 chefs

Welcome to Key West Food & Wine Festival 2027

A curated journey through the culinary heritage of five continents, featuring world-renowned chefs, their signature dishes, and the legendary wines that define their regions.
This journey spans five continents with iconic wines, each telling a story of terroir, history, and culture:
Africa: a smoky Pinotage,
Europe: a structured Bordeaux,
South America: a robust Malbec from Mendoza,
Oceania: a vibrant Marlborough Sauvignon Blanc,
North America: a cool-climate Pinot Noir from Oregon.

The Key West Food and Wine Festival is recognized as one of the best food and wine festivals in the country by the Travel Channel. If you’re a foodie, Key West is the place to be in January. With many unique events, held at spectacular island locations, this is an opportunity to enjoy a wide variety of wines and cuisine, with waterfront tastings, wine/food pairings, and local events around Key West.
Information courtesy of the Key West Food & Wine Festival – see their website for more details!

Florida Keys Seafood Festival
2027-02-13 - 2027-02-14 | Truman Waterfront Park, Key West, FL, United States
Florida Keys Seafood Festival
FEBRUARY 13-14, 2027

Two Days of Seafood, Music & Family Fun!

Join us for the 20th Annual Florida Keys Seafood Festival at Truman Waterfront Park in Key West. For just $10 admission, enjoy two full days of fresh, local seafood, live music, activities, and the vibrant island atmosphere that make this festival a Florida Keys favorite. This family-friendly event not only highlights the freshest local catch but also showcases the dedication of our commercial fishermen and women.

On the Menu…

Fried Fish baskets or platters with slaw and black beans & rice, Fried Shrimp basket, Grilled Spiny Lobster Platters, Stone Crab Claws with key lime mustard sauce, peel and eat Key West Pink Shrimp with cocktail sauce, Smoked Fish Dip with crackers, Creamy Lobster Bisque, Bahamian style Conch Chowder, Conch Ceviche, & Conch Fritters. Hot dogs and hamburgers also will be for sale. Beverages include beer, wine, rumaritas, rum runners, water, soda and coffees. Desserts include Key Lime Pie and other homemade treats.
Activities

Raffle to win $250 in seafood shipped to your home!
Great shopping and art
Fantastic entertainment all day

Children’s Eco Discovery Zone with activities

Adult beverages, beer, wine, frozen rumaritas with First Legal Rum
Event t-shirts, mugs and authentic lobster trap buoys for sale

The Florida Keys Seafood Festival directly supports the mission of the Florida Keys Commercial Fishermen’s Association (FKCFA), an organization dedicated to protecting, promoting, and sustaining the Keys’ commercial fishing community.

CREDIT: http://www.floridakeysseafoodfestival.com/
Information / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)

Key West Songwriters Festival
2027-04-28 - 2027-05-02 | Key West, Florida, Key West, FL, 33040, United States
The Key West Songwriters Festival.
4/28/27 – 5/2/27

The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. The festival has kicked off the careers of household names such as Kacey Musgraves, Florida Georgia Line, Jake Owen, Michael Ray, Randy Houser and Maren Morris. In its 27th year, KWSF has grown into a top destination for music lovers who flock to Key West for five days and nights of live music and storytelling from veteran songwriters and the next big hit-makers.
