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DTSTART;VALUE=DATE:20260712
DTEND;VALUE=DATE:20260716
DTSTAMP:20260706T193625Z
CREATED:20230105T195652Z
LAST-MODIFIED:20260706T193625Z
UID:686-1783814400-1784159999@www.historichideaways.com
SUMMARY:Del Brown Permit Tournament
DESCRIPTION:DEL BROWN 2026 TOURNAMENT\nJuly 12 – 15\, 2026\nCelebrate a Fly Fishing Legend: Del Brown\nThe 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. \nTest Your Mettle with 3 Days of Del Brown Permit Tournament Events\nThe 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. \n\n\nSchedule of Events\n\nSUNDAY\, JULY 12th\n5 PM Cocktails & Dinner – South of the Seven – Mile Marker 17 at Sugarloaf Lodge\nKick-off for tournament\, captains meeting\, hand out tournament bags\n\nMONDAY\, JULY 13th\n6:30 AM  Sign-in – Breakfast\, coffee and juice\, pick up lunch to go\n7:30 AM   Boats may depart for fishing\n3:30 PM   Lines Out** – Scorekeeping\, Appetizers and Drinks at South of the Seven\n5:00 PM   Scoring Closes – All releases must be recorded with scorekeeper  \nTUESDAY\, JULY 14th\n6:30 AM  Sign-in – Breakfast\, coffee and juice\, pick up lunch to go\n7:30 AM   Boats may depart for fishing\n3:30 PM   Lines Out** – Scorekeeping\, Appetizers and Drinks at South of the Seven\n5:00 PM   Scoring Closes – All releases must be recorded with scorekeeper  \nWEDNESDAY\, JULY 15th\n6:30 AM  Sign-in – Breakfast\, coffee and juice\, pick up lunch to go\n7:30 AM   Boats may depart for fishing\n3:30 PM   Lines Out** – Scorekeeping\, Appetizers and Drinks at South of the Seven\n5:00 PM   Scoring Closes – All releases must be recorded with scorekeeper  \n6:00 PM AWARDS IMMEDIATELY FOLLOWING LAST BOAT IN \n\n\n 
URL:https://www.historichideaways.com/event/del-brown-permit-tournament/
LOCATION:FL
CATEGORIES:Outdoor Activities
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DTSTART;VALUE=DATE:20260701
DTEND;VALUE=DATE:20260706
DTSTAMP:20260403T172632Z
CREATED:20230105T195325Z
LAST-MODIFIED:20260403T172632Z
UID:680-1782864000-1783295999@www.historichideaways.com
SUMMARY:Key Lime Festival
DESCRIPTION:2026 DATES – JULY 1 -5th\nWelcome 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!\n\n\n\n2026 SCHEDULE OF EVENTS!\nAll 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.)\n\n\n\n\n\n\n\n\n\n\n\nWednesday\, July 1st\nKey Lime Kick Off!  Live Music & Spirited Key Lime Entertainment!\nThe Avalon | 1317 Duval St | 5 – 8PM\nWelcome 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. \nKey Lime SPIRIT Pageant!\nHelp 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. \nLiving The Key Lime Life Dinner \nKaya 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.\n1st Course : Hurricane seasoned fresh Key west pinks and key lime cocktail sauce\n2nd Course : Cuban Hand Roll / mojo Roast pork /Swiss cheese /pickle/ egg roll cilantro key lime sauce\n3rd Course : Floribbean Fish – Locally caught fish\, Jamaican jerk seasoned Mahi Mahi\, Fresh Pineapple/mango salsa\, Goat cheese / coconut saffron rice\n*Chicken or Portobello options available\n4th Course : Made from scratch Key lime pie\nAfter dinner join us for live entertainment in the backyard bar.\n5-9PM\n$75/Person + Tax\nText or Call to book your reservation (305) 395-0213 \nTropicado’s Havana Nights – Key Lime Cocktail Party\nNEWLY REMODELED Tropicado @ Historic La Concha Hotel\, 430 Duval St\nKeep that Key Lime energy going!  Salsa\, rumba\, and cha-cha the night away while you enjoy some specialty crafted key lime cocktails.\n7-10PM\nFREE \n\n\n\n\n\n\n\n\n\n\n\nThursday\, July 2nd\nKey Lime Bike Tours\nJoin 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!\nTour starts at 9:30AM | 122 Ann St\nKey Lime Pie & Champagne Toast included on the tour\n$55 \n\n\n\n\n\nTICKETS\n\n\n\n\n\nKey Lime Pie Hop\nCHECK-IN LOCATION : Pilar Rum – Hemingway Social Club\nJoin 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!\nCheck-in 20 minutes prior to tour time\nTour Start Times:\n• 11AM\n• 11:30AM\n• Noon\n• 12:30PM\n• 1PM\n• 1:30PM\n$55.00 *includes pie samples and a FREE Key Lime Festival T-shirt! \n\n\n\n\n\nTICKETS\n\n\n\n\n\nTruman Waterfront Farmers Market – Key-Lime-O-Rama\n1-6PM\n21 E Quay Rd\, Truman Waterfront\nGet 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.\nVisit the Coast Guard booth for boater safety information\, games\, and giveaways! \n\n\n\n\n\n\n\n \n \n\n\n\n\n\n\n\nUS Coast Guard  \n\n\n\n\nSunset Cocktails on The Cutter Ingham \n21 Quay Rd\, Truman Waterfront \n6PM: Experience a live Search & Rescue Demonstration \n7-9PM: music by the United States Coast Guard Band and a Sunset Reception on the USCG Cutter Ingham! \nEnjoy Key Lime Cocktails and sample Key Lime desserts prepared by the United States Coast Guard Culinary Professionals. \n*DONATION SUGGESTED \n\n\n\n\n\n\n\n\n\n\nWheeling & Dealing Hot Wheels Race\nMary Ellen’s Bar\, 420 Applerouth Ln\nTest your driving skills on our Applerouth Track. Epic thrills and revving creativity. Do you have what it takes to win the race?!?\n4 – 6PM\nFinal Heat @ 5:30!\n$10 **includes (1) FREE BEER and (1) FREE Key Lime Festival Bandana \n\n\n\n\n\nTICKETS\n\n\n\n\n\nSloppy Joe’s Ultimate Key Lime Pie Smash Party!\nVote 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!\nSloppy Joe’s is “Still The Best Party In Town!”\n5:30 – 9:30PM \nPub Style Trivia with a Key Lime Twist\nSouthernmost Beach Resort on the Dewey Deck\, 1319 Duval St\nJoin 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!\nSpace is limited (50 players MAX) sign up NOW!\n6PM Sharp\n$20 – includes 5 rounds of trivia + (1) complimentary cocktail & chances to win prizes \n\n\n\n\n\nTICKETS\n\n\n\n\n\n\n\n\n\n \n \n\n\n\n\n\n\n\n\n\n\nFriday\, July 3rd\n5-Alarm Pie Challenge!\nAlex Vega Key West Firehouse Museum\, 1024 Grinnell Street\nStop 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.\n10AM – 2PM\nFREE –  Donations are appreciated to support the museum \nKey Lime-Tastic Pool Party\nBlue Flamingo Resort\, 3820 N Roosevelt Blvd\nBreak 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!\n11AM – 2PM\nFREE \nKey Lime Sip & Stroll\nIf 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.\n* Check-in at our Key Lime Festival Hub: First Flight Restaurant\, 301 Whitehead St. *\n3 – 7PM\n$55.00 \n\n\n\n\n\nTICKETS\n\n\n\n\n\nA Citrus Affair at Four Flamingos\, a Richard Blais Key West Kitchen\nOne-Night-Only Waterfront Key Lime Dinner Experience\nJoin 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.\nFrom 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. \n1st Course : Fresh Local Mahi-Mahi with Key Lime Leche de Tigre\, Pickle Daikon and Cilantro\n2nd Course : Miss Key West Pink Shrimp on Phyllo Spaghetti Dough with Habanero Labneh and Black Key Lime powder.\n3rd 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\n4th Course : Key Lime Bourbon Espresso Martini garnished with our house made Key Lime Pie.\n5-9PM\n$85/Person + Tax & Gratuity \n***Four Flamingos regular Menu will be available during regular business hours. Visit our website for menus.\nReserve your seat today and savor the zest of the summer. \n\n\n\n\n\nBook A Reservation\n\n\n\n\n\n\n\n\n\n\nSaturday\, July 4th\nRotary Club of Key West 4th of July 5K Run/Walk\nJoin the Rotary Club of Key West for their annual 4th of July 5K!\nAll proceeds will benefit the Edward B. Knight Scholarship Fund providing vocational scholarships to Monroe County Students.\nRace begins and ends at the Edward B. Knight Pier located at 1801 White Street.\nRace Starts @ 7:30AM\n$30 Kids 12 and under\n$45 until June 30th @ Midnight\n$50 July 1st – Race Day\nNEW THIS YEAR : ALL PARTICIPANTS WILL RECEIVE A RACE T-SHIRT! \n\n\n\n\n\nREGISTER HERE\n\n\n\n\n\nMatt’s Stock Island Key Lime Brunch\nEnjoy an unforgettable culinary experience at our dockside restaurant with unobstructed views of our state-of-the-art marina\, good vibes\, and your favorite cocktails.\nTry our new Key Lime inspired menu items thoughtfully crafted for all the Key Lime lovers out there.\n8AM-2PM \n\n\n\n\n\nBOOK RESERVATION\n\n\n\n\n\nKey Lime Vendor Village\n10AM – 4PM | Southernmost Beach Resort – 508 South St\nA 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.\nBe sure to pop in at Southernmost Beach Cafe for a cool beverage and some yummy food!\n10AM – 2PM\nWant to be a vendor at our Key Lime Vendor Village? Follow the link below:\nhttps://keylimefestival.com/key-lime-vendors \nWorld Famous Key Lime Pie Eating Championship \nSouthernmost Beach Café\, 1405 Duval St. 10AM – 2PM\nDo 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.\nRegistration at 10AM\nContest at 1:30 PM\nFREE to Watch | PRE-REGISTRATION = $30 to enter the Championship | Day of Entry = $50\n( ONLY 25 SPOTS AVAILABLE )\n*If you are entering the championship\, you must pay the entry fee and fill out the contestant form below.\nALL CONTESTANTS MUST BE 18 YEARS OR OLDER TO COMPETE.\nAll contest forms should be emailed to: keylimefest@gmail.com \n\n\n\n\n\nREGISTER HERE\n\n\n\n\nCONTESTANT FORM\n\n\n\n\n\nNEW THIS YEAR! Key Lime Kid Zone\nSouthernmost Beach Café\, 1405 Duval St. 10:30AM – 2PM\nSlime Making  & Slime decorating\, Sing A-longs/Music\, Story Telling & Reading\, Crafting/Coloring\, LEGOS\, Beach Games and MORE….\n@ 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! \nDante’s 4th of July Pool Party!\nDante’s Key West Pool Bar & Restaurant\, 955 Caroline St\nStars 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.\nDoors open at 11AM | Party Starts at NOON.\nFREE \nThe Rotary Club of Key West Presents: \nPatriotic Grill Out Under the Fireworks \nIndigenous Park\, 1801 White St.\nBring the whole family to the Patriotic Party by the Ed Knight Pier.\nEnjoy food\, music\, and of course\, fireworks!\nGrilling Hot Dogs and Burgers for purchase – Cash Bar Available\nFood and Bar @ 4:30PM | Fireworks @ Dark \n\n\n\n\n\n\n\n\n\n\n\nSunday\, July 5th\nMatt’s Stock Island Key Lime Brunch\nEnjoy an unforgettable culinary experience at our dockside restaurant with unobstructed views of our state-of-the-art marina\, good vibes\, and your favorite cocktails.\nTry our new Key Lime inspired menu items thoughtfully crafted for all the Key Lime lovers out there.\n8AM-2PM \n\n\n\n\n\nBOOK A RESERVATION\n\n\n\n\n\nKey West Artisan Market : Red\, White\, Blue & Green Edition\n10AM – 2PM | Indigenous Park @ Higgs Beach\, 1801 Atlantic Blvd\nKeep 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.\nFree entry | Free parking | Pet friendly | Walking and Biking encouraged!\nBYOB (Bring Your Own Bags) \n\n\n\n\n\nVENDOR REGISTRATION COMING SOON!\n\n\n\n\n\nKey Lime Pie Drop\nKey West Lighthouse\, 938 Whitehead St.\nCome 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.\n11AM – 2PM\nCheck in for Pie Droppers is from 11AM-NOON.\nPie Drop starts promptly at NOON.\nFREE to Watch | FREE to Enter the competition\nWinner will take home CASH MONEY $$$\n*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!\nAll contest forms should be emailed to: keylimefest@gmail.com \n\n\n\n\n\nREGISTER HERE\n\n\n\n\nCONTESTANT FORM\n\n\n\n\n\nJF Haden’s Battle of the Bartenders\nStarboard @ The Marker Hotel\, 200 Williams St\nGet 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!\nBattle begins at 2PM | Pool Party & LIVE MUSIC 2-5PM\nFREE \nFrozen Pie Pick-Up & Ship \nTake Key West home with you.\nKermit’s Key Lime Pie Shoppe – 200 Elizabeth St. & 335F Duval St (305) 296-0806\nKey West Key Lime Pie Co. – 511 Greene St. (305) 517-6720\nBe sure to call ahead and reserve your Pie!\nShipping dates based upon availability.
URL:https://www.historichideaways.com/event/key-lime-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260608
DTEND;VALUE=DATE:20260622
DTSTAMP:20260527T153716Z
CREATED:20260527T153716Z
LAST-MODIFIED:20260527T153716Z
UID:3176-1780876800-1782086399@www.historichideaways.com
SUMMARY:Summer Solstice Celebration
DESCRIPTION:JUNE 8-21\, 2026\n\n\n\n\nJoin us for our 2026 summer solstice celebration\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nFor 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\norganizations. Celebrate the season with nightly festivities\, community traditions\, and\nunforgettable sunsets in the heart of Key West.
URL:https://www.historichideaways.com/event/summer-solstice-celebration/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260604
DTEND;VALUE=DATE:20260608
DTSTAMP:20260527T152550Z
CREATED:20260527T152550Z
LAST-MODIFIED:20260527T152550Z
UID:3172-1780531200-1780876799@www.historichideaways.com
SUMMARY:CORALPALOOZA
DESCRIPTION:A GLOBAL MOVEMENT FOR OUR CORAL REEFS!\nTo 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.\nYear 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. \nRecognized 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. \nDive 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. \n(2026 Dive Days are SOLD OUT!) \n  \n\n\n\nUpper Keys Events\nDIVE DAYS \n\nThursday\, June 4th – AM & PM Dives  \nFriday\, June 5th – AM Dive  \nSaturday\, June 6th – AM & PM Dives \n\nCoralpalooza Community Night & Bazaar \nFriday\, June 5 | 6 PM – 8 PM  \nNew 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.  \n\n\n\n\n\n\n\nLower Keys Events\nDIVE DAYS \n\nFriday\, June 5th – PM Dive  \nSaturday\, June 6th – AM Dive\n\nCoralpalooza Social – Key West \nSaturday\, June 6 | 6 PM – 8 PM  \nJoin 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.  \nCoralpalooza at Key West Aquarium \nSunday\, June 7 | 10 AM – 4 PM  \n 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. 
URL:https://www.historichideaways.com/event/coralpalooza/
LOCATION:FL
CATEGORIES:Outdoor Activities
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2026/05/coralpalooza-logo-white-1.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260603
DTEND;VALUE=DATE:20260608
DTSTAMP:20260403T173100Z
CREATED:20230315T195648Z
LAST-MODIFIED:20260403T173100Z
UID:1373-1780444800-1780876799@www.historichideaways.com
SUMMARY:Key West Pride
DESCRIPTION:2026 Dates – JUNE 3rd – 7th\nCELEBRATE ONE HUMAN FAMILY\n \nThe 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.\nSupport the Key West Community\nKey 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.\n2026 SCHEDULE OF EVENTS!\nAll 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.)\n\n\n\nKicking off Pride Week – Saturday\, May 30th\n\n\n6:30 pm – Key West Pride Follies at the Key West Theater \nJoin 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. \n\n\n\nKey West Pride Begins – Wednesday\, June 3rd.\n\n\nNoon – Key West Business Guild Membership Luncheon: Pride Edition \nMore info coming soon! \n5-8 pm – The GOLD Party @ Island House for Men  \nNo 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. \n5:30 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 \n\n\n\n\n\n\n\nThursday\, June 4th.\n\n\nNoon – 4 pm –  Rainbow Runway: Poolside Glam-Off  at the Lighthouse Hotel – 902 Whitehead St \nCelebrate 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. \n6 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 \n9 pm – Key West Local Bartender Competition at Bourbon St. Pub – 724 Duval St \nLocal 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. \n\nFriday\, June 5th.\n\n\n\n\n\n\n11 am – Key West Pride Brunch Sail & Swim aboard the Argo Navis – 0(Zero) Duval St. \nCome 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 \n12 pm – ALL WELCOME “RU WET” Annual Pool Party at Alexander’s Guesthouse  – 1118 Fleming St. \nWe’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! \n12-5pm – Sausage Fest at Island House for Men – 1129 Fleming St.\nThe 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. \n4 pm – A Mojito Masterclass at Tropicado in La Concha Key West – 430 Duval St. \nJoin us at Tropicado Mojito Bar at La Concha Hotel for an immersive\, hands-on mojito experience in the heart of Key West! \nShake\, “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!\n\n8 pm – BERTHA: Grateful Drag hosted by Beatrix Dixie at the Key West Theater – 512 Eaton St\nThe 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 \n10 pm –Midnight Mass: A Heated Confession @ Island House for Men – 1129 Fleming St.\nA 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.\n\n\n\n\n\n\n\nSaturday\, June 6th.\n\n\n11:30 am – Paint the Town Proud Pub Roll starting at Bobby’s Monkey Bar – 900 Simonton St. \nJoin 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!\nThe tour departs promptly at 1:00 PM. This event is 21+ only. Tickets available HERE\n\n\n4 pm – “Celebration of Identity Through Color & Creativity” Street Fair on the 700-900 blocks of Duval Street\nCelebration 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. \nBring 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! \n10 pm – All Welcome Purgatory Party at Bourbon St. Pub – 724 Duval St.\nAdult 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.\n\n\n\n\n\n\n\nSunday\, June 7th.\n\n\n10 am – MCC Church Pride Service – 1215 Petronia St. \n10 am – Unity of the Keys Pride Service – 1011 Virginia St. \n11:30 am – Key West Pride Drunken Drag Brunch at Mangoes Key West – 700 Duval St. \nMangoes 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. \nImportant 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. \nNoon – HOT NAKED SUNDAY at the Island House for Men 1129 Fleming St. \nAfter church\, and before tea dance\, comes Island House! A Gay Key West tradition for over 20 years! All gay\, bi\, queer\, trans + brothers welcome. \n7 pm – Color the Island Pride Parade \nJoin 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.  \n\n\n\n\n\nDaily Activities\n\n\n\n\nMuseums: 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 \nLand 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. \nWater 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
URL:https://www.historichideaways.com/event/key-west-pride/
LOCATION:FL
CATEGORIES:Festivals
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260417
DTEND;VALUE=DATE:20260427
DTSTAMP:20260403T173359Z
CREATED:20230105T194217Z
LAST-MODIFIED:20260403T173359Z
UID:657-1776384000-1777247999@www.historichideaways.com
SUMMARY:Annual Conch Republic Independence Celebration
DESCRIPTION:Annual Conch Republic Independence Celebration!\n\n\nIt’s Fun FOR ALL And ALL For FUN\nThe 44th Anniversary of Our Independence!\n\n\n\n\nCalling Conch Republic Patriots\, Pirates and Partiers – Declare Your FUN-dependence!\n \nThe Founding of the Conch Republic\nThe 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”.\n\n\n\n\n\n\nAll 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.)\n\n\n\n\n\n\n \n\n\n\n\n\n\n\n 
URL:https://www.historichideaways.com/event/annual-conch-republic-independence-celebration/
LOCATION:FL
CATEGORIES:Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260403
DTEND;VALUE=DATE:20260405
DTSTAMP:20251117T210930Z
CREATED:20251117T210930Z
LAST-MODIFIED:20251117T210930Z
UID:2797-1775174400-1775347199@www.historichideaways.com
SUMMARY:My Maria - By Andrew Russell
DESCRIPTION:My Maria\n\n\n\n\nBy Andrew Russell  \n\n\n\n\nDirected by Morgan Green\n\n\nFri Apr 3 & Sat Apr 4\, 8pm\nA 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?
URL:https://www.historichideaways.com/event/my-maria-by-andrew-russell/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20260330T200000
DTEND;TZID=America/New_York:20260330T230000
DTSTAMP:20251215T190758Z
CREATED:20251215T190758Z
LAST-MODIFIED:20251215T190758Z
UID:2818-1774900800-1774911600@www.historichideaways.com
SUMMARY:Randy Roberts and Donna McKechnie
DESCRIPTION:Randy Roberts and Donna McKechnie\n\n\n\n\nSpotlight Cabaret curated by Randy Roberts\nTwo 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.
URL:https://www.historichideaways.com/event/randy-roberts-and-donna-mckechnie/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/12/Spotlight-by-Randy-Roberts-logo-768x478-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260323
DTEND;VALUE=DATE:20260324
DTSTAMP:20251117T194540Z
CREATED:20230105T194612Z
LAST-MODIFIED:20251117T194540Z
UID:666-1774224000-1774310399@www.historichideaways.com
SUMMARY:Taste of Key West
DESCRIPTION:Annual Taste of Key West! Join us for Taste of Key West 2026 at Truman Waterfront on Monday\, March 23rd!\n\nThis open-air event promises an assortment of beverages and palate-pleasing plates. Restaurants and food vendors from across the Lower Keys and Key West donate their staffs’ time and extraordinary culinary talents to create delectable small plates. Foodies can stroll edibles and drinkables\, ranging from seafood\, tropical and Caribbean flavors\, to European dishes\, vegetarian offerings\, and desserts. Buy tickets based upon what looks best! In addition to the scrumptious food\, libations are free flowing throughout the event. A selection of wines from across the globe are provided by Republic National Distributing Company. Connoisseurs can expect to be wowed with vintages from vineyards and wineries. If wine is not up your alley\, no worries — a vast selection of beers is also offered.\nTaste of Key West gates open at 6PM for FREE general admission. Food/beverage tickets and packages will be available for purchase soon!\nMoney raised helps benefit AH Monroe who specialize in healthcare and assistance for people living with HIV/AIDS.Biking or walking is strongly encouraged for both convenience and to work off those calories!\n\nBOOK YOUR VACATION RENTAL FOR TASTE OF KEY WEST \nDon’t wait to book your Key West vacation rental if you’re planning on attending Taste of Key West. Choose from our selection of luxury homes\, vacation rentals with a pool\, pet-friendly rentals\, condos or townhomes. \nBrowse Vacation Rentals>>>
URL:https://www.historichideaways.com/event/taste-of-key-west/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260320
DTEND;VALUE=DATE:20260322
DTSTAMP:20251117T210742Z
CREATED:20251117T210742Z
LAST-MODIFIED:20251117T210742Z
UID:2794-1773964800-1774137599@www.historichideaways.com
SUMMARY:Mom’s Best Friend - By Dan McCabe
DESCRIPTION:Mom’s Best Friend      \n\n\n\n\nBy Dan McCabe\n\n\n\n\nDirected by Kate Whoriskey\n\n\nFri Mar 20 & Sat Mar 21\, 8pm\nJune and her adult daughter\, Christine\, talk on the phone three times a day—best friends\, or so June believed. But when Christine abruptly cuts off all contact with a single\, shocking email\, June must confront life without her closest ally and reevaluate how she is perceived by others.
URL:https://www.historichideaways.com/event/moms-best-friend-by-dan-mccabe/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/11/GOLDEN-HOUR-8.5-x-7-in-12-1536x1265-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260304
DTEND;VALUE=DATE:20260322
DTSTAMP:20251117T211201Z
CREATED:20250722T183002Z
LAST-MODIFIED:20251117T211201Z
UID:2672-1772582400-1774137599@www.historichideaways.com
SUMMARY:Once
DESCRIPTION:Mar 4\, 2026 – Mar 21\, 2026\nWinner of eight Tony Awards\, including Best Musical\, Once tells the story of a disillusioned Dublin street musician whose music — and life — are transformed by an unexpected encounter with a woman who believes in him. Intimate\, powerful\, and deeply moving\, this modern classic captures the magic of connection.
URL:https://www.historichideaways.com/event/once/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260213
DTEND;VALUE=DATE:20260215
DTSTAMP:20251117T210524Z
CREATED:20251117T210524Z
LAST-MODIFIED:20251117T210524Z
UID:2791-1770940800-1771113599@www.historichideaways.com
SUMMARY:The Patrons - By Nick Gandiello
DESCRIPTION:The Patrons\n\n\n\n\nBy Nick Gandiello\n\n\n\n\n\nDirected by Aaron Rossini\n\n\nFri Feb 13 & Sat Feb 14\, 8pm\n\nIn 1963\, Head Librarian Mrs. Quarter is training Rhonda to serve the community amid budget cuts and a staff shortage. Unbeknownst to Quarter\, Rhonda allows teenage patron Adam to check out a controversial book\, which is soon voted for removal from the shelves by the county. As local tempers flare against the library\, the staff must choose how far they will go to protect their ideals and each other.
URL:https://www.historichideaways.com/event/the-patrons-by-nick-gandiello/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/11/GOLDEN-HOUR-8.5-x-7-in-12-1536x1265-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260130
DTEND;VALUE=DATE:20260201
DTSTAMP:20251117T210316Z
CREATED:20251117T210316Z
LAST-MODIFIED:20251117T210316Z
UID:2787-1769731200-1769903999@www.historichideaways.com
SUMMARY:The Starters - By Laura Winters
DESCRIPTION:The Starters\n\n\n\n\nBy Laura Winters\n\n\n\n\nDirected by Ashley Brooke Monroe\n\n\nFri Jan 30 & Sat Jan 31\, 8pm\n\nAt 35 years old\, Matt Shears is one of the oldest right tackles in the NFL. He and his wife\, Emily\, are planning for Matt’s retirement. But after Matt’s team goes to the Super Bowl\, Matt is determined to play for one more year. Emily is equally determined to keep him off the team and out of harm’s way.
URL:https://www.historichideaways.com/event/the-starters-by-laura-winters/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/11/GOLDEN-HOUR-8.5-x-7-in-12-1536x1265-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260127
DTEND;VALUE=DATE:20260201
DTSTAMP:20251117T203818Z
CREATED:20230105T192332Z
LAST-MODIFIED:20251117T203818Z
UID:638-1769472000-1769903999@www.historichideaways.com
SUMMARY:Annual Mile 0 Fest Key West
DESCRIPTION:5-DAY MUSIC FEST IN PARADISE\n\nFive Nights of Music in Paradise\n\n\nCalling all music lovers! Immerse yourself in the laid back island vibes of Mile 0 Fest Key West\, a premier boutique music festival. Each year boasts a stellar lineup of established and rising artists performing in beautiful outdoor venues. Experience all Key West has to offer while listening to your favorite bands and making new life-long friends. \n\n\nAmazing Music \n\nMile 0 Fest is known for its incredible lineup of Red Dirt and Americana music. From well-known headliners to up-and-coming artists\, there’s something for everyone.  Catch daytime shows at the beach\, on the pier\, at a pool party or on a music sail – then join us at the Amphitheater each evening! In addition to the music\, attendees can enjoy a variety of fun activities\, such as Live Music Sails\, Pool Parties & more! The festival takes advantage of Key West’s natural beauty and laid-back island vibe\, providing a unique and unforgettable experience for music fans and vacationers alike. Join us for five days (or longer!) of incredible music\, breathtaking scenery\, and unforgettable memories at Mile 0 Fest. \n \n \nBOOK YOUR VACATION RENTAL FOR THE Mile 0 Fest \n\n\nDon’t wait to book your Key West vacation rental if you’re planning on attending the Mile 0 Fest. Choose from our selection of luxury homes\, vacation rentals with a pool\, pet friendly rentals\, condos or townhomes. \nBrowse Vacation Rentals>>>
URL:https://www.historichideaways.com/event/annual-mile-0-fest-key-west/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts,Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260126
DTEND;VALUE=DATE:20260127
DTSTAMP:20250722T182222Z
CREATED:20250722T182222Z
LAST-MODIFIED:20250722T182222Z
UID:2663-1769385600-1769471999@www.historichideaways.com
SUMMARY:The Phil Collins Experience
DESCRIPTION:Mon January 26\, 2026 \nThe Phil Collins Experience\nThe Phil Collins Experience is a dynamic multi-media production that pays tribute to the legendary music of Phil Collins and Genesis. Known as the most authentic Phil Collins tribute in the U.S.\, this show captivates audiences with its faithful recreation of the sights\, sounds\, and emotions of Collins’ iconic performances.The Phil Collins Experience is fronted by Englishman\, Terry Adams Jr. who perfectly captures the look\, sound\, and feel of Phil Collins. The Phil Collins Experience transports fans back to the golden era of hits like In the Air Tonight\, Against All Odds\, and Sussudio. \nAdams\, like Collins\, is a skilled drummer who performs on a left-handed drum kit adding to the authenticity of the show. Adams is backed by his world class 12 piece band\, complete with a sensational horn section and backup singers that will have audiences on their feet all night long. With its attention to musical and visual detail\, The Phil Collins Experience brings the spirit of Phil Collins and Genesis to life\, making it a must-see production for fans across the nation. Phil Collins is one of only three recording artists\, along with Paul McCartney and Michael Jackson\, who have sold over 100 million records worldwide both as solo artists and separately as principal members of a band. \nHe has received eight Grammy Awards\, six Brit Awards (winning Best British Male Artist three times)\, two Golden Globe Awards\, one Academy Award\, and a Disney Legend Award. The role of Phil Collins is performed to perfection by KC Magazine’s BEST MALE VOCALIST Terry Adams Jr. \nOur British born and raised front man will make you forget that he’s not Phil! Terry Adams Jr brings the look\, the sound\, the emotion\, the energy. The true feel of Phil Collins! \nBacked by his world class 12 piece band complete with a sensational horn section and back up singers\, Terry Adams Jr happens to be a world class drummer himself that plays his drums left handed just like Phil Collins for the true experience. \nSince 2018 our show has been wowing audiences at festivals\, theaters and private events nationwide. \nImmerse yourself in the world of Phil Collins and Genesis with their greatest hits like: “In The Air Tonight “\, “Sussudio”\, “Invisible Touch”\, “That’s All”\, and many many more! \nThis show is NOT TO BE MISSED! \n\nVenue Information:\nKey West Theater\n512 Eaton St\nKey West\, FL\, 33040
URL:https://www.historichideaways.com/event/the-phil-collins-experience/
LOCATION:FL
CATEGORIES:Concerts
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260121
DTEND;VALUE=DATE:20260122
DTSTAMP:20250722T183419Z
CREATED:20250722T183419Z
LAST-MODIFIED:20250722T183419Z
UID:2675-1768953600-1769039999@www.historichideaways.com
SUMMARY:The Music of ABBA
DESCRIPTION:A fun colorful family show\, all the way from Sweden! \nWith hits like Mamma Mia\, Waterloo\, Fernando and Dancing Queen\, ABBA\, Sweden’s biggest music export group ever\, made their way into the hearts of people all around the world. \nWe will give you the closest ABBA experience you’ll ever going to get with some of the most experienced and talented musicians and singers from Sweden in a tribute that will bring you down memory lane through stunning\, mirroring images of their stage costumes\, hairstyles\, and voices. \nYou will be dancing in the aisles\, singing along to your favorite ABBA song and we assure you\, this will be a night you’ll never forget.
URL:https://www.historichideaways.com/event/the-music-of-abba/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2025/07/Screenshot2025-05-23203710.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260113
DTEND;VALUE=DATE:20260114
DTSTAMP:20250722T181957Z
CREATED:20250722T181957Z
LAST-MODIFIED:20250722T181957Z
UID:2660-1768262400-1768348799@www.historichideaways.com
SUMMARY:Los Lobos
DESCRIPTION:It’s a matter of time. 50 years to be exact. And in that time Los Lobos have created an unprecedented body of work\, a legacy of greatness. The numbers are staggering: 100+ gigs a year for five decades running\, crossing millions of miles to rock millions of fans. And that’s just at the live shows. In between they’ve recorded 17 studio albums\, 7 live LPs\, 3 compilations\, 2 EPs\, 2 DVDs\, and contributed 40+ guest appearances on their friends’ recordings—all garnering 4 Grammys\, an Austin City Limits Hall of Fame induction\, the ALMA Ritchie Valens Pioneer Award\, NEA and Hispanic Heritage Foundation Honors\, Congressional recognitions\, plus countless “Keys to the City” and “Los Lobos Day” celebrations. And those are just a few of the highlights. But beyond all the hoopla and applause (and the source of it all\, really) is the tremendous heart. Rather\, hearts. Cinco corazones. Five blood brothers who have dedicated their off-stage time to helping others\, working for peace and justice\, penning some of the most literate and important music of their time\, transforming the hard cries from the East L.A. barrio into songs of hope\, tales of common folk finding ways to endure. The young wolves were weaned on late-night radio’s soul\, R&B\, and doo-wop. Were cured through the African-American currents of the blues\, jazz\, and rock ‘n’ roll. An amalgam. As proud Chicanos\, their songs have always glistened with the distillation from their Mexican and Latin American roots—nourished by Norteña and rancheras\, buoyed by bolero and cumbias\, soaring on the rhythms of son huasteco and son jarocho. Los Lobos have helped spread the rich diversity of cultures across every continent\, throughout the global community. Kids in Antwerp now know about Aztlán. Residents of Luxor and Ghana are crooning Lalo Guerrero. People from Laos and Bulgaria are belting “La Bamba”—all thanks to The Wolves as cultural ambassadors. Talk about a living legacy. Talk about a productive half century. And in the true rebel spirit\, they did it all on their own terms\, against formula. For the ages. To our delight. Quite simply\, they are one of the tightest\, one of the best\, one of the most prolific bands ever. And\, amazingly\, with the original founding members as the pack the entire time. Unprecedented. As their liner notes put it\, quite simply: “Los Lobos still are David Hidalgo\, Louie Pérez\, Jr.\, Cesar Rosas\, Conrad Lozano\, Steve Berlin.”\n\nVenue Information:\nKey West Theater\n512 Eaton St\nKey West\, FL\, 33040
URL:https://www.historichideaways.com/event/los-lobos/
LOCATION:FL
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/07/uploadedimage-jpg_6846fd2dcbe29.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20260108
DTEND;VALUE=DATE:20260130
DTSTAMP:20251215T190428Z
CREATED:20251215T190428Z
LAST-MODIFIED:20251215T190428Z
UID:2815-1767830400-1769731199@www.historichideaways.com
SUMMARY:WORM: A Cuban American Odyssey
DESCRIPTION:WORM: A Cuban American Odyssey\nEdel Rodriguez\nWorm: A Cuban American Odyssey explores themes of migration\, displacement\, and identity through original drawings from Rodriguez’s acclaimed graphic memoir Worm\, bold new paintings\, silkscreened posters\, and the political art from the covers of TIME and Der Spiegel that made him an international voice. Also on view are personal artifacts\, family photos\, and visual source material that shaped the book\, offering a rich and layered look at a life lived between two worlds. \nThe exhibition traces Rodriguez’s extraordinary journey—from a boyhood in Cold War Cuba to his family’s escape during the Mariel boatlift\, when they were branded gusanos (“worms”) by Castro. Arriving in Key West by shrimping boat in 1980\, Rodriguez would go on to become one of the most prominent political artists of our time\, known for provocative magazine covers\, and artwork that champions truth\, freedom\, and the immigrant experience.
URL:https://www.historichideaways.com/event/worm-a-cuban-american-odyssey/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/12/edel-rodriguez-1024x687-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20251204
DTEND;VALUE=DATE:20251221
DTSTAMP:20250722T182817Z
CREATED:20250722T182817Z
LAST-MODIFIED:20250722T182817Z
UID:2669-1764806400-1766275199@www.historichideaways.com
SUMMARY:Some Enchanted Evening
DESCRIPTION:Dec 4\, 2025 – Dec 20\, 2025\nA stunning revue of Rodgers & Hammerstein’s most treasured songs\, this elegant theatrical presentation brings five performers into a world of timeless music — from backstage intimacy to full-stage splendor. A heartfelt tribute to the golden age of Broadway.
URL:https://www.historichideaways.com/event/some-enchanted-evening/
LOCATION:FL
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2025/07/Enchanted_Poster_WEB-scaled-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20251015
DTEND;VALUE=DATE:20251025
DTSTAMP:20250722T182615Z
CREATED:20230629T180001Z
LAST-MODIFIED:20250722T182615Z
UID:1701-1760486400-1761350399@www.historichideaways.com
SUMMARY:The Rocky Horror Show
DESCRIPTION:Oct 15\, 2025 – Oct 24\, 2025\nCelebrate the 50th Anniversary of “The Rocky Horror Picture Show” and the 5th Anniversary of this Fantasy Fest favorite at the Waterfront Playhouse! Richard O’Brien’s outrageous cult classic returns for an encore run filled with thrills\, chills\, and wild audience participation. Costumes encouraged!
URL:https://www.historichideaways.com/event/the-rocky-horror-show/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/06/RockyHorror_Poster_WEB-scaled-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250523
DTEND;VALUE=DATE:20250525
DTSTAMP:20240730T190821Z
CREATED:20240730T190726Z
LAST-MODIFIED:20240730T190821Z
UID:2287-1747958400-1748131199@www.historichideaways.com
SUMMARY:STOMP!
DESCRIPTION:May 23rd – 24th\, 2025\nMatchboxes\, brooms\, garbage cans\, Zippo lighters\, and more fill the stage with energizing beats at STOMP: the inventive and invigorating stage show that’s dance\, music\, and theatrical performance blended together in one electrifying rhythm.
URL:https://www.historichideaways.com/event/2287/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/07/379890_340574769299565_446984372_n.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20250425T200000
DTEND;TZID=America/New_York:20250425T220000
DTSTAMP:20240730T190247Z
CREATED:20240730T190247Z
LAST-MODIFIED:20240730T190247Z
UID:2284-1745611200-1745618400@www.historichideaways.com
SUMMARY:The Rat Pack: One More Time!
DESCRIPTION:April 5th\, 2025\nRING–A-DING-DING! THE BEST RAT PACK SHOW RE-TURNS! Frank Sinatra\, Dean Martin and Sammy Davis\, Jr. return to stages all across America as the famous and infamous Rat Pack is resurrected by our three critically acclaimed entertainers. Relive those amazing nights with our international star performers. This show is the real deal. You’ll feel like you’re back at the Sands Hotel with a smooth martini in one hand and a top-notch show in front of you. Love ya\, baby!
URL:https://www.historichideaways.com/event/the-rat-pack-one-more-time/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/07/RatPack.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250416
DTEND;VALUE=DATE:20250504
DTSTAMP:20240621T185725Z
CREATED:20240621T185725Z
LAST-MODIFIED:20240621T185725Z
UID:2226-1744761600-1746316799@www.historichideaways.com
SUMMARY:Wait Until Dark
DESCRIPTION:Wait Until Dark\n\nThe final show of the season is\, according to the New York Post\, “A first rate shocker… The suspense drama we’ve long awaited eagerly… A classic”. Written in 1966 by Frederick Knott and then adapted by Jeffrey Hatcher in 2013\, this is the story of a blind woman in Greenwich Village in post WWII America imperiled by con men who are trying to recover diamonds that have accidentally come into her possession.  It is “Wait Until Dark” April 16th to May 3rd.
URL:https://www.historichideaways.com/event/wait-until-dark/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/06/WaitUntilDark_24_x36_PRINT.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20250329T200000
DTEND;TZID=America/New_York:20250329T230000
DTSTAMP:20240730T185951Z
CREATED:20240730T185951Z
LAST-MODIFIED:20240730T185951Z
UID:2281-1743278400-1743289200@www.historichideaways.com
SUMMARY:Free Fallin\, The Tom Petty Concert Experience!
DESCRIPTION:March 29th\, 2025\nGet ready for an epic live show with Free Fallin\, The Tom Petty Concert Experience!\nEnjoy this vibrant musical journey remembering the one and only\, Tom Petty!  Watch as these highly skilled musicians perform his iconic hits. Perfect for those who’ve grown up to classics like ‘American Girl’\, ‘Free Fallin’ and ‘Mary Jane’s Last Dance’. This performance is sure to be an unforgettable and emotional ride.
URL:https://www.historichideaways.com/event/free-fallin-the-tom-petty-concert-experience/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/07/FreeFallin-logo2023-blackSquare.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20250323T190000
DTEND;TZID=America/New_York:20250323T230000
DTSTAMP:20240730T185721Z
CREATED:20240730T185721Z
LAST-MODIFIED:20240730T185721Z
UID:2278-1742756400-1742770800@www.historichideaways.com
SUMMARY:The Peking Acrobats
DESCRIPTION:March 23rd\, 2025\nTHE PEKING ACROBATS® have redefined audience perceptions of Chinese acrobatics. They perform daring maneuvers atop a precarious pagoda of chairs and display their technical prowess at such arts as trick-cycling\, precision tumbling\, juggling\, somersaulting\, and gymnastics. They push the limits of human ability\, defying gravity with amazing displays of contortion\, flexibility\, and control. The time-honored Chinese music coalesces with high-tech special effects and awe-inspiring acrobatic feats\, creating an exuberant entertainment event with the festive pageantry of a Chinese Carnival.
URL:https://www.historichideaways.com/event/the-peking-acrobats/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/07/the-peking-acrobats-8211-blue-gate-performing-arts-center-8211-20250215-1480x832-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250306
DTEND;VALUE=DATE:20250328
DTSTAMP:20250218T160805Z
CREATED:20250218T160707Z
LAST-MODIFIED:20250218T160805Z
UID:2504-1741219200-1743119999@www.historichideaways.com
SUMMARY:Field Theory -- Tory Mata
DESCRIPTION:MARCH 6-27\n2025 / Exhibition\nField Theory by Tory Mata\nMata’s latest work delves into the deeply human questions of belonging\, meaning\, and the passage of time. By blending scientific and spiritual themes with artistic expression\, Mata reveals the shared truths and connections between these realms. Her art transforms these concepts into metaphors\, shedding light on the complexities of human life and the universal threads that bind us all together.\nsponsored by Historic Hideaways \n 
URL:https://www.historichideaways.com/event/field-theory-tory-mata/
LOCATION:The Studios of Key West\, 533 Eaton St\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts
ATTACH;FMTTYPE=image/png:https://www.historichideaways.com/wp-content/uploads/2025/02/0gsehnv9.png
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250226
DTEND;VALUE=DATE:20250323
DTSTAMP:20240621T185322Z
CREATED:20240621T185322Z
LAST-MODIFIED:20240621T185322Z
UID:2220-1740528000-1742687999@www.historichideaways.com
SUMMARY:La Cage Aux Folles
DESCRIPTION:We are proud to present a classic of American Musical Theatre. The original production of this show ran for more than four years and over 1700 performances. It won six Tony Awards including Best Musical\, Best Score\, and Best Book.\nBut more than that\, it’s an important story about family\, tolerance\, love\, and understanding- The Waterfront Playhouse is proud to present: “La Cage Aux Folles”\, February 26th to March 22nd.
URL:https://www.historichideaways.com/event/la-cage-aux-folles/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/06/LaCage_24_x36_PRINT.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250212
DTEND;VALUE=DATE:20250213
DTSTAMP:20240621T190500Z
CREATED:20240621T190500Z
LAST-MODIFIED:20240621T190500Z
UID:2233-1739318400-1739404799@www.historichideaways.com
SUMMARY:The Four Phantoms in Concert
DESCRIPTION:FEBRUARY 12\, 2025\n\n\n\n\nAn extravagant celebration of the iconic music of Broad­way and more\, The Four Phantoms brings together four Phantoms from the Tony Award-winning The Phan­tom of the Opera for an unforgettable evening of entertain­ment. The Four Phantoms features an extraordinary quar­tet of performers\, including Brent Barrett\, John Cudia\, Franc D’Ambrosio\, and Ciarán Sheehan\, under the musical direction of Ryan Shirar.
URL:https://www.historichideaways.com/event/the-four-phantoms-in-concert/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/06/the-four-phantoms.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250208
DTEND;VALUE=DATE:20250209
DTSTAMP:20240621T190251Z
CREATED:20240621T190251Z
LAST-MODIFIED:20240621T190251Z
UID:2229-1738972800-1739059199@www.historichideaways.com
SUMMARY:A Blonde\, Brunette\, & Some Duets
DESCRIPTION:FEBRUARY 8\, 2025\n\n\n\n\nEric McCormack and Laura Bell Bundy! Together\, they bring their magnetic chemistry from Broadway’s The Cottage to the stage\, promising a night of unforgettable entertainment that spans Broadway hits\, cinematic charm\, and chart-topping tunes.
URL:https://www.historichideaways.com/event/a-blonde-brunette-some-duets/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/06/Eric-and-LBB-1295-×-495-px.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20250122
DTEND;VALUE=DATE:20250209
DTSTAMP:20240621T185525Z
CREATED:20240621T185525Z
LAST-MODIFIED:20240621T185525Z
UID:2223-1737504000-1739059199@www.historichideaways.com
SUMMARY:The Angel Next Door
DESCRIPTION:This wonderfully funny script captures the sheer joy\, sophistication\, and wit of 1940’s screwball comedies. This will be a Florida Premiere and only the fourth production of this recently published new farce.  Brace yourself for what a critic called “a perfect storm of comedic chaos\, irresistible charm\, and rapid-fire banter”- Paul Slade Smith’s “The Angel Next Door” January 22nd to February 8th.
URL:https://www.historichideaways.com/event/the-angel-next-door/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2024/06/AngelNextDoor_24_x36__PRINT.jpg
END:VEVENT
END:VCALENDAR