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UID:2784-1788393600-1788825599@www.historichideaways.com
SUMMARY:Just a Few Friends - Key West
DESCRIPTION:2026 JAFF SCHEDULE Preliminary schedule — subject to change\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.)\nFull schedule & tickets on sale May 1 \n\nApril 28 for package holders\nApril 30 for badge holders\n\n\nWEDNESDAY\, SEPTEMBER 2 \n11:00 AM — JAFF Headquarters | Key West First Legal Rum \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n6:00 PM — Early Welcome Party at the Chart Room | Pier House \n\nTHURSDAY\, SEPTEMBER 3 \n9:30 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound \n11:00 AM — Cooking Show: Grits n Grunts | Key West Cooking Show \n11:00 AM — Friends of Bubba HQ | Key West First Legal Rum \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:00 PM — Truman Waterfront Farmers Market | Truman Waterfront Park \n2:15 PM — Tales from the Chartroom | Pier House \n5:00 PM — Cheeseburger Beach Battle and Tribute Concert | Southernmost on the Beach \n7:00 PM — “Open Mic / No Mic Night” at Andy’s Cabana | Andy’s Cabana \n8:00 PM — After Party | TBD \n\nFRIDAY\, SEPTEMBER 4 \n8:00 AM — Plogging the Keys Waterfront Cleanup | Reef Relief @ the Historic Seaport \n8:00 AM — Painting Paradise: A Guided Plein Air Experience (Session 1) | Shrimp Boat Sound \n9:00 AM — Island Time Brunch Buffett | TBD \n11:00 AM — Key West’s Favorite Son City Proclamation | Shrimp Boat Sound \n11:00 AM — Cliff Cody Performance at Proclamation | Shrimp Boat Sound \n11:00 AM — Friends of Bubba HQ | Key West First Legal Rum \n12:00 PM — Coconut Telegraph Trolley Tour | Pier House \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:00 PM — Screening with Panel Discussion | Tropic or San Carlos \n2:30 PM — VIP Special Edition: Jimmy Buffett Tribute Show | Comedy Key West \n3:45 PM — Tales from the Chartroom | Pier House \n5:00 PM — Duval Street Party with the Landshark Band | TBD \n9:00 PM — Outdoor Movie | Southernmost Pint Brewpub \n\nSATURDAY\, SEPTEMBER 5 \n9:00 AM — Painting Paradise: A Guided Plein Air Experience (Session 2) | Louis Backyard \n10:00 AM — Private Distillery Tour with Paul Menta | Key West Legal Rum \n10:00 AM — Coconut Telegraph Trolley Tour | Pier House \n10:00 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound \n10:00 AM — Sails Up: Intro to Sailing Experience | Key West Sailing Center \n11:00 AM — Ultimate Friend’s Private Distillery Tour with Paul Menta | Key West Legal Rum \n11:00 AM — Best Friend’s VIP Live Music Sail | Fury Water Adventures \n11:00 AM — Author/Photographer Book Signing | Books & Books @ Studios of KW \n11:00 AM — Friends of Bubba HQ | Key West First Legal Rum \n11:00 AM — Back to the Island Beach Party | Bourbon Street Pub \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:15 PM — Tales from the Chartroom | Pier House \n2:00 PM — Milagro Margarita Historic Seaport Bar Stroll | The Marker Resort \n2:00 PM — Milagro Margarita Duval Street Bar Stroll | La Concha \n5:00 PM — Early Access: Table Seating (JFF VIPs) | Big Stage \n5:30 PM — Early Access: Entry (JFF Badge Holders) | Big Stage \n6:00 PM — Doors Open (GA) | Big Stage \n6:30 PM — Mike Stack & Friends | Big Stage \n6:30 PM — Cruisin’ Tiki Sunset & Music Cruise | Cruisin’ Tikis @ Mac’s Place \n6:30 PM — Latitude Adjustment Sunset Sail | The Dock @ Sunset Pier \n8:00 PM — Changes in Latitudes: Concert ft. the Wheeland Brothers | Sunset Pier \n8:00 PM — Outdoor Movie | Southernmost Pint Brewpub \n\nSUNDAY\, SEPTEMBER 6 \n10:00 AM — Coconut Telegraph Trolley Tour | Pier House \n10:00 AM — Bubbles Brunch Sail | The Dock @ Sunset Pier \n11:00 AM — Book Signing | Books & Books @ Studios of KW \n11:00 AM — JAFF Headquarters | Key West First Legal Rum \n12:00 PM — Wheeland Brothers Poolside Acoustic | Ocean Key Resort \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n1:00 PM — Best Friend VIP Private Show | Margaritaville Restaurant \n1:00 PM — Pool Party at the Marker | The Marker Resort \n1:15 PM — Tales from the Chartroom | Pier House \n5:00 PM — Second Line Memorial Walking Parade | 100 Duval Street \n6:00 PM — Key West Artisan Market at the Party in the Park | Truman Waterfront Park \n6:00 PM — Party in the Park: Tribute to Bubba | Truman Waterfront Park \n\nMONDAY\, SEPTEMBER 7 \n10:00 AM — Just a Few Friends Walking Tour | Shrimp Boat Sound \n10:00 AM — Tin Cup Sailing Adventure | Danger Charters \n11:00 AM — JAFF Headquarters | Key West First Legal Rum \n12:30 PM — A Pirate Looks Back\, the Key West Jimmy Buffett Tribute Show | Comedy Key West \n1:00 PM — Chart Room Daily Hangout Headquarters | Pier House \n2:00 PM — Tales from the Chartroom | Pier House \n2:30 PM — Pencil Thin Mustache Contest | Chart Room \n5:00 PM — Early Access: Table Seating (JFF VIPs) | Sunset Pier \n5:30 PM — Early Access: Entry (JFF Badge Holders) | Sunset Pier \n6:00 PM — Doors Open (GA) | Sunset Pier \n6:30 PM — Come Monday: Cayman & the Mango Men | Sunset Pier \n6:30 PM — Island Tiki Sunset & Music Cruise | Cruisin’ Tikis @ Mac’s Place \n8:30 PM — Last Call | TBD
URL:https://www.historichideaways.com/event/just-a-few-friends-key-west/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Concerts,Festivals,Outdoor Activities
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DTSTART;VALUE=DATE:20261016
DTEND;VALUE=DATE:20261026
DTSTAMP:20260706T200801Z
CREATED:20230105T184839Z
LAST-MODIFIED:20260706T200801Z
UID:623-1792108800-1792972799@www.historichideaways.com
SUMMARY:Key West Fantasy Fest!
DESCRIPTION:October 16 – 25\, 2026\n2026 Theme: Musical Icons & Iconic Musicals\n \nFantasy 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!\nFantasy Fest 2026 Daily Events Guide\nA day-by-day guide to what’s happening around Key West during Fantasy Fest for guests planning their stay with Historic Hideaways. \nAll 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.)\n\n  \nDaily Diversions\n\n\nYour Picture with the King & Queen Sculpture\nFreeOpen Daily 9AM–5PM510 Greene Street\nStop 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. \n\n\n801 Cabaret — Sushi & The 801 Girls\n21+Oct 17–23 & 26 · 9PM & 11PM801 Duval Street\nThe 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. \n\n\nBody Art & Sunsets at Sunset Pier\nFrom $60Oct 17–25 · Starts 1PM0 Duval Street\, Sunset Pier\nFemme 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. \n\n\nFantasy Facade — sponsored by Haunted Key West\nFree to enterRegister by Mon Oct 13 · Judged Mon Oct 20\nA 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. \n\n\nFury Water Adventures Discount\nValid Oct 16–31\nSave 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. \n\n\nHappy Hour at Orchid Key Inn Bar\nBar open daily 12PM–10PMHappy Hour 5–7PM\nIntimate poolside bar with a boutique wine list\, mixologist-crafted cocktails\, and house-made infusions with fresh-squeezed juices. \n\n\nIVs in the Keys\nCall 305-395-8245\nKey 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+. \n\n\nKaraoke Party\nNightly 8PM–2AM618 Duval St\, Key West Empourium\nNightly karaoke throughout Fantasy Fest week at the Karaoke Lounge\, hosted by Stars Karaoke Club and DJ Rico. \n\n\nPhoto Op: Fest Letters All Day\nFreeOpen daily from 11:30AM631 Greene Street\nSnap a selfie with the giant Fantasy Fest letters at Conch Republic Seafood Company. Happy hour daily 4–7PM in the bar & patio. \n\n\nPot Stop Selfie Contest\n21+Greeen House locations\nGrab 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. \n\n\nSloppy Joe’s Hangover Headquarters\nDaily from 9AM · Kitchen opens 10AM201 Duval Street\nMorning-after recovery all week long with Deep Eddy Vodka cocktails\, Bloody Marys\, Dulce Vida frozen margaritas\, live entertainment\, and giveaways. \n\n\n\n\n16\n\nFriday · October 16 \nKickoff Weekend\n\n\n\nBahama Village Goombay Festival\nFreeFamily-FriendlyNoon–MidnightPetronia & Emma St\nA street party in the historic Bahama Village neighborhood with island arts\, crafts\, food\, and nonstop music ranging from reggae to soca. \n\n\nBarbie’s Pink Pool Party for Breast Cancer Awareness\n$20 donation4–7PMThe Marker Key West Harbor Resort\nBarbie/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. \n\n\nHappily Fur-Ever After Royal Coronation\nFree general admissionDoors 6PM · Show 7PMCoffee Butler Amphitheater\, 21 Quay Rd\nFlorida 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. \n\n\nThe Dave Matthews Tribute Band\nFree7PMSunset Pier\nA 5-piece tribute band bringing the energy and intimacy of a live Dave Matthews Band show to Sunset Pier. \n\n\n\n\n17\n\nSaturday · October 17 \n\n\n\n\nBahama Village Goombay Festival\nFreeFamily-FriendlyNoon–MidnightPetronia & Emma St\nContinues from Friday — island arts\, crafts\, food\, and live music at the corner of Petronia and Emma Street. \n\n\nRum with Bum\nFree admission10AM–2PMAlex Vega Key West Firehouse Museum\, 1024 Grinnell St\nA 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. \n\n\nMermaid Mayhem at the Blue Flamingo Resort\n12–4PM3820 N Roosevelt Blvd\nAn official Fantasy Fest undersea-themed pool party at the new Blue Flamingo Resort. \n\n\nWitches in the Hammock at Crane Point\n$15 adults / $5 kidsFamily-Friendly6:30–9PMCrane Point Hammock\, Marathon — 5550 Overseas Hwy\nLantern 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. \n\n\nThat Arena Rock Show\nFree7PMSunset Pier\nA high-energy tribute concert to classic ’70s and ’80s rock at Sunset Pier. \n\n\n\n\n18\n\nSunday · October 18 \n\n\n\n\nKey West Artisan Market at Higgs Beach\nFree admission10AM–2PM1707 White Street\nFantasy 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. \n\n\nMedusa’s Forbidden Lagoon\n12–4PMMargaritaville Beach House\, 2001 S Roosevelt Blvd\nA poolside party with a mythical/serpent theme — DJ\, food\, and drinks\, with jewel-tone and metallic dress encouraged. \n\n\nThat Arena Rock Show\nFree7–9PMSunset Pier\nRepeat performance of the classic rock tribute show at Sunset Pier. \n\n\n\n\n19\n\nMonday · October 19 \n\n\n\n\nHavana Cabana’s Duck\, Duck\, Booze Pool Party\nFree12–4PM3420 N Roosevelt Blvd · 305-294-5541\nA rubber-duck-themed pool party with beverage samples\, swag\, and a chance to win a $200 gift card plus other giveaways from The Tazzle. \n\n\nMargs & Makers\n12–5PMSacred Space Gallery\, 529 Southard St\nMargaritas and a pop-up shop featuring 30 women artists at this all-female gallery. \n\n\nMrs. Roper Romp\nFree (donations to charity)5PM0 Duval Street\, Sunset Pier\nA “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. \n\n\nA Green Parrot Beatles Tribute\nFree5:30\, 9:00 & 11:00PM601 Whitehead Street\nKey West’s own Beatle Band performs three sets\, with an optional ’60s dress-up theme for the crowd. \n\n\nFantasy Fest 5K Run/Walk\n6PM startTiki House Key West\, Duval Street\n“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. \n\n\nMasquarade Monday Wine Dinner presented by Bogle Wines\n$150 (dinner & wine\, gratuity extra)Doors 6PM · Dinner 7PMA&B Lobster House\, 700 Front St\nRegency-era masquerade ball and multi-course wine dinner with live music. Masks required; reserve seats at Keystix.com. \n\n\nMartini Monday at Virgilio’s\n$7 martinis6PM–close524 Duval St\n$7 martinis all night\, plus live music and food. \n\n\nFemme Fantasy Fete: Vixens & Villains\n21+\, Women-Only$25 / $45 VIP9PM–untilMangoes\, 700 Duval St\nA dark-fairytale-themed women-only evening with cocktails\, a costume contest\, VIP lounge access\, mask-making\, and a photo booth. \n\n\nKinky Carnival\nAdult content\, cash only$75Open bar 8–11PM · Party until 1AMFirst Flight\, 301 Whitehead St\nKey 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. \n\n\nSloppy Joe’s Comic Book Cape-ers Party\nLive music from 10AM201 Duval Street\nThemed costume party at Sloppy Joe’s with live entertainment throughout the day and night. \n\n\nTops or Bottoms Underwear Party\nAdult content\, men’s event10PM–4AMNew Orleans House\, 724 Duval St · 305-293-9800\nPrivate underwear party with free clothes check. \n\n\n\n\n20\n\nTuesday · October 20 \nTutu Tuesday\n\n\n\nDante’s 4th of July Party\n$10 cover11AM–5PM951 Caroline St · 305-293-5123\nPatriotic-themed pool party with food and drink specials. \n\n\nRum Revelation\, A Cocktail Journey ft. Captain Morgan\n$99 ppClasses at 12 & 2PMKey West Cooking Show\, 291 Front St\, Ste 207\nRum tasting and cocktail-making class featuring Captain Morgan White and Spiced\, with two cocktails made and a swag bag included. \n\n\nStorybook Splash Pool Party at Winslow’s Bungalows\n12–4PM725 Truman Avenue\nStorybook-character costume pool party with two pools\, live entertainment\, food/drink specials\, a costume contest\, and hourly vacation raffles. \n\n\nFlorida Keys Council of the Arts Poster Signing Party\nFree3–5PMLa Concha Hotel\, 430 Duval Street\nMeet the winning 2026 poster designer\, get posters/shirts/swag\, and sample wine courtesy of Bogle Wines. \n\n\nTutu Tuesday Pre-Party Bar Crawl\nSteps off 6PMMary Ellen’s\, 420 Applerouth Lane\nA walking parade pre-party with a drink stop\, feeding into the main Tutu Tuesday event; parade pass includes entry to the Tutu Party. \n\n\nFantasy Fest Spooky Trivia\nSold Out6PMSouthernmost Beach Resort\, 1319 Duval St\nSix-round Halloween-themed trivia night; costumed players get bonus points. This one is already sold out per the listing. \n\n\nTutu Tuesday: Tuesday Night Fever & Our Silly Robot Friends\n$30 advance / $40 day-ofDoors 6PM — no tutu\, no entryCaroline St district (4 venues)\n15th 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. \n\n\nTay Tay Tuesday: In Your Wildest Dreams\nFree6–9PMSunset Pier\nLive Taylor Swift tribute concert performed by local artist Meghan Barter. \n\n\nTutu Salsa Sessions\nFree7–9PMSouthernmost Beach Café\, 1319 Duval St\nSalsa dance instruction while wearing tutus\, sponsored by Dulce Vida Organic Tequila\, with margarita and sangria specials. \n\n\nCocktails for Animal Tails\, presented by Dirty Monkey\n$408–11PM (early entry 7:30PM with pre-sale)Rick’s Bar\, 202 Duval St\nCharity 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. \n\n\nCapt. Tony’s Party in Plaid\nFree8PM428 Greene St · 305-294-1838\nPlaid-costume party with music and drinks at Capt. Tony’s. \n\n\n\n\n21\n\nWednesday · October 21 \n\n\n\n\nSloppy Joe’s Slumber Party\nLive music from 10AM · Contest signup 8:15PM201 Duval Street\nSleepwear-costume contest themed to “Bedtime Stories & Magical Monsters.” Prizes: $500 / $250 / $100 Sloppy Joe’s gift cards; band “Nightbreakers” plays after the contest. \n\n\nSwayzees Pajama Pool Party\nFree2–5PMSoMo’s Shores Pool\nPajama or swimwear pool party with live music from Les Greene and the Swayzees\, sponsored by Empress Gin. \n\n\nBowties & Birthday Suits\n21+\, adult content\, gay men’s event$50 cash/credit5–8PM (resort access thru Thu 4AM)Island House\, 1129 Fleming St\nClothing-optional pool party at Island House resort; no costumes needed. Admission includes locker\, towels\, and extended resort access. Photo ID required. \n\n\nMonsters Under the Sea Costume Contest\n$25 + $5 charity donation7PM–MidnightMargaritaville Cafe\, 500 Duval St\nUnderwater-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. \n\n\nThe 4th Annual Party Like a Rockstar\n6PM–Midnight (Guitar Shred-Off at 8PM)618 Duval St\, Key West Empourium\nGuitar 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. \n\n\nThe Bedtime Bizarre at the Blue Flamingo Resort\n6–10PM3820 N Roosevelt Blvd\n“Bedtime Stories & Magical Monsters”-themed evening event with lounges\, cocktails\, live entertainment\, and immersive décor. Pajama-chic to fully costumed attire encouraged. \n\n\nPet Masquerade\n$25/entry to compete · free to watchRegistration 5PM · Show 6:30PMKey West Amphitheater\, Truman Waterfront Park\, 21 E Quay Rd\nPet 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. \n\n\nStudio 69 Disco Party\n$15 / $45 open bar / $75 open bar + dinner7PM till late (open bar 7–9PM)The Alamo\, 4 Charles St\n’70s disco-themed dance party with local DJs Scott Gerke and Chris Cohen. \n\n\nWharfstock at the Schooner Wharf Bar\nNo cover7PM–midnight202 William St · 305-292-9520\n1960s Woodstock-themed sit-in with live music from “That Hippie Band\,” costume prizes for sexiest hippie chick and grooviest dude (judged 8:30PM). \n\n\nLUV2GLOW: Liquid Frequency\n21+$30–$40 GA / $100 VIP8PM–4AMRick’s Upstairs\n14th 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). \n\n\nDesire Male Fetish Party\nAdult content\, men’s event10PM–4AMNew Orleans House\, 724 Duval St · 305-293-9800\nPrivate fetish party with fetish attire encouraged and free clothes check. \n\n\n\n\n22\n\nThursday · October 22 \n\n\n\n\nBerkshire Hathaway Parade of Homes Mega Open House\nFree11AM–3PMKey Largo to Key West\nKeys-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. \n\n\nSouthernmost Scavenger Hunt’s 6th Annual Bar Crawl\n$45 ppCheck-in 2PM · Crawl 2:30–4:30PM\nTeam 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. \n\n\nLes Greene & The Swayzees Pajama Pool Party (Take 2)\nFree2–5PMThe Marker Resort\nSecond round of the pajama/swimwear pool party with live music\, sponsored by Dulce Vida Organic Tequila. \n\n\nDante’s 19th Annual Halos & Horns Pool Party\n$25 (benefits Autism Society of the Florida Keys)Doors 11AM · Party noon–6PM951 Caroline St · 305-293-5123\nAngel/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. \n\n\nFunk It Up Party\nFree to watch5:30\, 9:30 & 11PMGreen Parrot Bar\, 601 Whitehead St\nLive sets from funk band Funk You\, blending modern and vintage dance grooves. \n\n\nStudio 430 Dance Club Under the Stars\nDJ 6–10PMLa Concha Hotel & Spa\, 430 Duval Street\nRooftop pool-deck lounge party with classic cocktails and DJ sets. \n\n\n42nd Annual Headdress Ball\n$30 GA – $320 premium tableDoors 6:30PM · Show 8PMCoffee Butler Amphitheater\, Truman Waterfront Park\nThe 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. \n\n\n5th Annual Rock the Tatas Contest\n$25 (benefits Making Strides Against Breast Cancer)Doors 5PM · Contest 7PMHanks Hair of the Dog Saloon\, 409 Caroline St\nBreast cancer awareness costume/charisma contest with a $500 first prize plus crown and sash\, live music from 9PM. \n\n\nCowboys\, Cowgirls\, & Monsters\n$15 / $45 open bar / $75 open bar + dinner7PM till late (open bar 7–9PM)The Alamo\, 4 Charles St\nWestern/monster costume party with local DJs Scott Gerke and Chris Cohen and late-night food. \n\n\nFat Tuesday Pink Party\n8PM–close305 Duval Street\nPink-costume party with live entertainment and a costume contest ($500/$250/$100 bar tabs). Note: source text says “Thursday 10/23” — confirm date. \n\n\nSloppy Joe’s 46th Annual Toga Party\nLive music from 10AM · Contest signup 8:15PM201 Duval Street\nLong-running toga-costume contest\, individual or groups of 2–4. Prizes $500/$250/$100 Sloppy Joe’s gift cards; “Nightbreakers” plays after. \n\n\nExposed at the Bourbon St. Pub\nAdult content\, open to all$100 presale / $110 day-ofDoors 9PM · 10PM–4AM724 Duval Street\nPoolside 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. \n\n\nIrish Kevin’s Annual 80’s Party\nNo coverLive music open to close · Band at 10PM211 Duval St · 305-292-1262\n’80s-themed party with a dedicated cover band taking the stage at 10PM. \n\n\n\n\n23\n\nFriday · October 23 \nStreet Fair Begins\n\n\n\nFantasy Fest Street Fair & Costume Promenade\nFree to attendArts & Crafts noon–10PM · Food noon–1AMDuval Street\nDuval Street’s signature mile-long street fair: arts\, crafts\, and food on Friday\, with Saturday shifting focus to food served late into the night. \n\n\nBourbon St. Pub’s Afternoon Pool Party\nCover charge (free clothes check)Noon–~5PMNew Orleans House\, 724 Duval St · 305-293-9800\nPoolside dance party / street fair T-Dance with live DJs\, drag queens\, and games. \n\n\nSouthernmost Playboy House — Beach Bunny Pool Party Bash\nAdults only$30Noon–5PM1400 Duval Street · 305-296-3141\nOceanfront infinity-pool party with DJ Hazard and drink specials; bunny ears required for topless sunbathing per venue policy. \n\n\nComparsa at the San Carlos Street Party\nFree entryNoon–Midnight516 Duval St · 305-294-3887\nCuban music and dancing street party hosted by the San Carlos Institute\, with a mojito bar. \n\n\nCaptain Morgan’s Masquerade March (The Locals’ Parade)\nFreeBlock party 4PM · Steps off 5:30PMFrances & Petronia St\nA 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. \n\n\nThe 4th Annual Captain Morgan’s Pirate Party\nNo cover6:30–10PM (bar until 1AM)618 Duval St\, Key West Empourium\nPirate-themed party with nautical music and a costume contest paying $500/$300/$200. \n\n\nSurf’s Up at the Hog’s Breath Saloon\nFree7PM400 Front Street · 305-296-4222\nSurfer-costume party with live music and drink specials. \n\n\n25th Annual Living Art Expo\nFreeParty 7PM · Contest 8PMSunset Pier\nBody-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. \n\n\nAquaplex Slay Queen — Chapter 3\, Part 1: Nightmare on Duval St.\n$35 / $200 booth8PM711 Duval St\nHorror-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. \n\n\nKinky Couples Party hosted by RubberDoll\nCouples only\, adult content$275–$500Shows 8PM & 11PM801 Bourbon Bar\, 801 Duval St\nCouples-exclusive event with a performance from latex entertainer RubberDoll. Pre-registration required; no re-entry once you leave. Repeats Saturday. \n\n\nMidnight Mass: A Heated Gaythering\nAdult content\, gay men’s event$60 cash/credit10PM–2AM (resort access thru Sat 4AM)Island House\, 1129 Fleming St\nAdults-only late-night event at Island House resort. Admission includes first drink\, locker\, towels\, and extended resort access. Photo ID required. \n\n\nPlexXx\nAdult content$25 cover10PM504 Angela St\nLate-night dance party at the Birdcage Cabaret hosted by Holly Dae\, featuring an international DJ. \n\n\n\n\n24\n\nSaturday · October 24 \nParade Day\n\n\n\nFantasy Tennis Tournament\n$75 donation8–11:30AMHiggs Beach Tennis Courts\nLadder-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. \n\n\nFantasy Fest Street Fair & Costume Promenade\nFree to attendNoon till early hoursDuval Street\nSaturday’s Street Fair shifts focus to food\, running late into the night alongside the parade. \n\n\nComparsa at the San Carlos Street Party\nFree entryNoon–Midnight516 Duval St · 305-294-3887\nCuban music\, dancing\, and a mojito bar hosted by the San Carlos Institute. \n\n\nNew Orleans House Pool Party\nClothing optionalCover charge (free clothes check)Noon–5PM724 Duval St · 305-293-9800\nParade-day pool party with live DJ and pool games. \n\n\nSouthernmost Scavenger Hunt’s 6th Annual Bar Crawl\n$45 ppCheck-in 2PM · Crawl 2:30–4:30PM\nTeam 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. \n\n\nBourbon St. Pub’s VIP Balcony Bash\n$200 VIP presale\, 150 availableDoors 6PM · 7–10PMNew Orleans House\, 724 Duval St\nGrand-balcony parade viewing with open bar and catered buffet\, private entrance and restrooms. Tickets from 305-293-9800 or keystix.com. \n\n\nFirst Flight Parade Viewing Party\n$125–$150++Check-in 5:30PM · 6–9PMFirst Flight Island Restaurant & Brewery\nDinner buffet and 3-hour open bar with a choice of sidewalk chair\, indoor table\, or porch-chair seating for the parade. \n\n\nMangoes Fantasy Fest Parade Party\n$80 presale / $100 day-ofDoors 6PM · Parade 7PMMangoes\, 700 Duval St\nElevated patio parade-viewing with drink specials\, a special dinner menu\, and live piano from Dave Bootle after the parade. \n\n\nNightcaps & Nightgowns: A Moonlight Pajama Viewing Party\n$250–$350Seating begins 6PMHellings Curry Museum\nReserved-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. \n\n\nViva’s Grand Finale Viewing & Dinner Parade Party\n$90 / $135 (open bar 6–9PM)6PM (check-in 5:30PM)Viva Argentinian Steakhouse\, 903 Duval St\nOutdoor tiki bar and air-conditioned indoor viewing\, live music and DJ\, plus a live 8-piece Argentine band after the parade. \n\n\nDeep Eddy Vodka Fantasy Fest Parade\nFreeSteps off 7PMDuval Street\nThe main event — floats\, costumes\, and dance groups down Duval Street in front of a crowd historically numbering in the tens of thousands. \n\n\nParade Viewing Party at La Te Da\n6–10PM1125 Duval Street\nStreet-side parade viewing emceed by WEOW’s Rude Girl. \n\n\nAquaplex Slay Queen — Chapter 3\, Part 2: Dreamcatcher\n$35 / $200 booth10PM711 Duval St\nWhimsical mythical-creatures-themed drag show\, second half of the two-night Slay Queen event. Reservations recommended. \n\n\nKinky Couples Party hosted by RubberDoll\nCouples only\, adult content$275–$500Shows 8PM & 11PM801 Bourbon Bar\, 801 Duval St\nSecond night of the couples-only latex/fetish-themed event with RubberDoll. \n\n\nThe Blue Party at the Backyard Bar\n8PM onward618 Duval St\, Key West Empourium\nOcean/mermaid-themed party with Jeff Clark’s All Star Band; partial proceeds support Sea Basecamp. \n\n\n\n\n25\n\nSunday · October 25 \nWind Down\n\n\n\nFantasy Pickleball Tournament\n$100 donation8–11:30AMHiggs Beach Pickleball Courts\nCharity 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. \n\n\nChildren’s Day\nFamily eventNoon–5PMBayview Park\, Truman Ave & Eisenhower Dr · 305-292-8912\nFamily-friendly festival with food\, rides\, games\, arts and crafts\, and a kids’ costume contest. \n\n\nAfter Church Pool Party\nAdult content\, gay men’s event$50 cash/credit12–4PM (resort access thru Mon 4AM)Island House\, 1129 Fleming St\nClothing-optional pool party with a Sunday raffle. Admission includes locker and towels. Photo ID required. \n\n\nHangover Pool Party at SoMo’s Pineapple Pool\nFree1–4PMSouthernmost Beach Resort\nRecovery-day pool party with food/drink specials and a live DJ. Note: source text says “Sunday\, 10/26” — confirm date. \n\n\n“The Fat Lady Sings” Tea Dance\n$54–8PMLa Te Da\, 1125 Duval St · 305-296-6706\nTraditionally the last official event of Fantasy Fest week\, with music from DJ Rude Girl. \n\n\nReggae Lou & The Kind Budz Rehab Pool Party\nFree12–5PMThe Marker Resort\, 200 William St\nSponsored by Dirty Monkey Banana Peanut Butter Whiskey — live reggae music\, drink specials\, and two pools. \n\n\n\n\n28\n\nWednesday · October 28 \nPost-Fest Bonus\n\n\n\nGolf Cart Facade Viewing Tour\n6:30–9PMGreeen House Mothership\, 3128 N Roosevelt Blvd\nPost-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.
URL:https://www.historichideaways.com/event/fantasy-fest/
LOCATION:FL
CATEGORIES:Concerts,Festivals,Outdoor Activities,Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270428
DTEND;VALUE=DATE:20270503
DTSTAMP:20260706T194000Z
CREATED:20230105T194740Z
LAST-MODIFIED:20260706T194000Z
UID:669-1808870400-1809302399@www.historichideaways.com
SUMMARY:Key West Songwriters Festival
DESCRIPTION:The Key West Songwriters Festival.\n4/28/27 – 5/2/27 \n\nThe 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.
URL:https://www.historichideaways.com/event/key-west-songwriters-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Concerts,Festivals
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