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SUMMARY:Key West oktoBREWfest
DESCRIPTION:October 1 – 5\, 2026 · Grand Tasting: Saturday\, October 3\, 3–8pm\nSouthernmost Beach Resort\, 1319 Duval Street\, and venues across the island \nKey West oktoBREWfest is an island-wide beer festival hosted by the Key West Sunrise Rotary of the Conch Republic and the Southernmost Beach Resort. It’s a fully nonprofit event\, with proceeds going to the Rotary’s scholarship fund for local students. The Grand Tasting anchors the week\, with pool parties\, pairings\, and tap takeovers scattered across the island on either side of it. All events are 21 and over. \nThursday\, October 1\nPool Floatie Chug & Race · 1–4pm · Shores Pool\, Southernmost Beach Resort · Free\, registration required. Presented by Cerveceria La Tropical Brewing.\nGrilled Cheese & Beer Pairing with Pub Style Trivia · 6pm · Dewey Deck\, Southernmost Beach Resort · Four gourmet grilled cheese sandwiches paired with Florida Keys Brewing beers\, plus trivia. Reservations required; available with or without food. \nFriday\, October 2\nPineapple Pool Party & Belly Flop Contest · 1–4pm · Pineapple Pool\, Southernmost Beach Resort · DJ\, beer samples\, and a belly flop contest. Presented by Islamorada Brewing & Distillery. Free\, RSVP required.\nBrews & Blues Concert & Tasting · 5–7pm · The Backyard Pool & Social Club\, Blue Flamingo Resort\, 3280 N. Roosevelt Blvd · Live blues poolside. Free\, reservation required. \nSaturday\, October 3 — Grand Tasting\n2026 oktoBREWfest Grand Tasting · 3–8pm · Southernmost Beach Resort · More than 60 beer vendors and over 225 beers\, with live entertainment. The Southernmost Beach Café will be open with beer hall food specials and cocktails. \nVIP — $125 · Early 3pm admission\, commemorative poster\, stainless steel VIP mug\, and a Bavarian-themed buffet\nGeneral Admission — $50 · 5–8pm\nDesignated Driver — $20 · Admission\, soft drinks\, and a coupon for one food item \nSunday\, October 4\nPool Party & Concert by Jerico · 12–4pm · Winslow’s Bungalows\, 725 Truman Ave · Live music\, drink specials\, prizes.\n3 Daughters Brewing Drink & Draw · 2–4pm · The Marker\, 200 William St · A drawing contest with a bar tab on the line.\nSurprise Tap Takeover · 3–6pm · Bearded Lady\, 417 Southard St · Beer specials\, prizes\, live entertainment. \nMonday\, October 5\nBrewfest / Green Parrot Charity Bingo · 7pm · Green Parrot Bar\, 601 Whitehead St · All proceeds to the Sunrise Rotary scholarship fund. Drink specials and prizes. \nTickets and registration at keystix.com/brewfest. \nSchedule subject to change. Information courtesy of Key West oktoBREWfest — visit keywestbrewfest.beer for tickets and complete details.
URL:https://www.historichideaways.com/event/key-west-oktobrewfest/
CATEGORIES:Festivals,Outdoor Activities
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DTSTART;VALUE=DATE:20261016
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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/
CATEGORIES:Concerts,Festivals,Outdoor Activities,Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/Screenshot-2025-11-17-151555.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20261022
DTEND;VALUE=DATE:20261023
DTSTAMP:20260831T185914Z
CREATED:20230629T182247Z
LAST-MODIFIED:20260831T185914Z
UID:1720-1792627200-1792713599@www.historichideaways.com
SUMMARY:Key West Headdress Ball
DESCRIPTION:Key West Headdress Ball\nThursday\, October 22\, 2026 · Coffee Butler Amphitheater at Truman Waterfront Park\nDoors 6:30pm · Show 8:00pm\nThe Key West Business Guild presents the 43rd Anniversary Headdress Ball\, one of the most anticipated nights of Fantasy Fest. \nLegendary Key West entertainer Randy Roberts returns as host\, with music by WEOW’s RudeGirl. Twelve to fifteen contestants take the stage to reveal their headdress creations — judged from the shoulders up — competing for a $2\,500 grand prize. \nNew Award Categories\nThe Ball introduces six categories this year\, recognizing different kinds of artistic achievement: \n\nHead Above the Rest — $2\,500 · The night’s top honor\, for the creation that best combines artistic vision\, originality\, craftsmanship\, presentation\, and overall impact\nSpirit of Fantasy Fest — $1\,000 · For the creation that best captures the official Fantasy Fest theme\nPretenders in Paradise — $750 · A nod to the beloved former Fantasy Fest costume competition\, for the contestant whose costume and headdress read as one cohesive work\nGlow Getter — $500 · For the headdress that makes the biggest impact through creative illumination — LEDs\, neon\, or other lighting effects\nDream Team — $500 · For two or more artists who combine their talents into a single\, visually stunning presentation\nSize Doesn’t Matter — $500 · For the artist who makes a bold impression with a more compact design\n\nTotal prize purse: $6\,000 \nBetween competition rounds\, the evening features performances by some of Key West’s most celebrated local entertainers. Full bar service and specialty wines are available\, and food can be preordered and delivered right to your table. \nTickets\nPrices do not include fees \n\nPremium Table for 4 — $400 (includes your choice of a bottle of wine\, a bucket of beer\, or non-alcoholic beverage selections)\nVIP Table for 4 — $290\nReserved Chair Seating — $40\nGeneral Admission\, grass seating — $30\n\nThe Headdress Ball celebrates the artistic expression and inclusive spirit that have made Key West one of the world’s most distinctive destinations\, and this night one of Fantasy Fest’s signature events. \nThis event sells out every year — reserve your seats early. For tickets\, contestant information\, or to enter the competition\, visit gaykeywestfl.com/headdress-ball or call 305-294-4603. \nSchedule subject to change. Information courtesy of the Key West Business Guild — see their website for complete details.
URL:https://www.historichideaways.com/event/key-west-headdress-ball/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Arts,Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20261101
DTEND;VALUE=DATE:20261109
DTSTAMP:20260831T185407Z
CREATED:20231018T183151Z
LAST-MODIFIED:20260831T185407Z
UID:1914-1793491200-1794182399@www.historichideaways.com
SUMMARY:Race World Offshore (aka Boat Races!)
DESCRIPTION:45th Annual Key West Offshore World Championship\nNovember 1–8\, 2026 · Truman Waterfront Park\, Key West\nThe 45th Annual XINSURANCE Key West World Championship runs Sunday\, November 1 through Sunday\, November 8\, 2026\, at Truman Waterfront Park. It’s the season finale of the Race World Offshore calendar and the oldest continuously run event on the RWO schedule — the only stop with its own standalone world championship title alongside APBA National and UIM points. The course runs a lap of just over four miles through Key West Harbor\, mixing calm inshore water with rougher open stretches\, with boats topping 140 mph on the fastest legs. \nBeyond the Race Village at Truman Waterfront\, good vantage points include Mallory Square\, Fort Zachary Taylor Historic State Park\, Sunset Pier\, and Simonton Street Beach\, plus harbor front hotels overlooking the course. General admission is $25 per day at the Outer Mole entrance. Children 12 and under and military personnel with ID get in free. \nRace Week Schedule \nSunday\, November 1\nParade participants line up on Duval Street · 3:30pm\nFirst State Bank World’s Fastest Boat Parade down Duval Street · 4:00pm \nWednesday\, November 4 — Race Day (Bonus Day)\nGates open at Truman Waterfront Park · 9:00am\nRacing begins\, seven races through the day · 10:00am\nWinner’s Circle award ceremony at the Outer Mole · after racing \nFriday\, November 6 — Race Day\nGates open · 9:00am\nRacing begins · 10:00am\nWinner’s Circle award ceremony at the Outer Mole · after racing \nSunday\, November 8 — Race Day\, Finale\nGates open · 9:00am\nRacing begins · 10:00am\nUIM World Champion Awards & Closing Ceremony at Key West Amphitheater · 5:00pm \nEach race day carries seven scheduled race times\, running from 10:00am through 3:15pm. Race Village at Truman Waterfront is open on race days with food\, drinks\, and merchandise. Additional race-week events — the annual boat building contest\, VIP parties\, and driver meet-and-greets — are listed on the official schedule. \nGetting There\nTruman Waterfront Park sits at the end of Southard Street on the west side of the island. Parking nearby is limited\, so organizers encourage rideshare\, bicycles (helmets required)\, or the free Duval Loop bus. Coolers\, outside food and drink\, drones\, weapons\, scooters\, tents\, backpacks\, and golf carts aren’t permitted on site\, and personal items are subject to search by NAS Key West security. \nSchedule subject to change. Information courtesy of Race World Offshore — see raceworldoffshore.com for tickets\, the full schedule\, event maps\, and updates.
URL:https://www.historichideaways.com/event/boat_races/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270115
DTEND;VALUE=DATE:20270118
DTSTAMP:20260831T184853Z
CREATED:20230105T153545Z
LAST-MODIFIED:20260831T184853Z
UID:592-1799971200-1800230399@www.historichideaways.com
SUMMARY:29th Annual Key West Half Marathon & Runfest
DESCRIPTION:29th Annual Key West Half Marathon & Runfest®\nJanuary 13–18\, 2027 · Race weekend January 15–17 \nKey West offers a multitude of exciting experiences\, from its diverse restaurants and vibrant nightlife to the numerous museums and art galleries. The wide range of water sports options adds an extra layer of adventure\, making it an unforgettable destination. And let’s not forget the intriguing fact of having 400 bars on an island that’s only 2 x 4 miles. Set aside some extra time to explore all that Key West has to offer. \nSchedule of Events\nWednesday\, January 13\nVolunteer Check-In & Party · 11am–1:30pm · Sailfish Bar at Half Shell Raw Bar\, 231 Margaret St \nThursday\, January 14\nRunner’s Meet & Greet with drink specials · 4:30–6pm · Sailfish Bar\, Half Shell Raw Bar \nFriday\, January 15\nRunner’s Expo & Packet Pick-Up · 2–7pm · Outside Half Shell Raw Bar\nLate bib pick-up (bibs only) · 7:15–10pm · Fit2Run\, 211 Duval St\nAll-day drink specials at Half Shell Raw Bar \nSaturday\, January 16 — 5K & 10K\nBag check · 6–6:45am · In front of Salute! On the Beach\, 1000 Atlantic Blvd\n5K start/finish · 7am · Higgs Beach\n10K start/finish · 8am · Higgs Beach\nConcert & Awards Party with Homebred Band featuring Dave Richards · 8–11am · Outside Salute! On the Beach\nOverall winners announced · 9:30am\nRunner’s Expo & Packet Pick-Up · 1–6pm · Outside Half Shell Raw Bar\nPresentation by Dr. Kellee Reed · 3:30pm\nLate bib pick-up (bibs only) · 7–10pm · Fit2Run\, 211 Duval St\nEarly breakfast and all-day food/drink specials at Salute! and Half Shell \nSunday\, January 17 — Half Marathon & 8K\nBag check · 6–6:45am · Lot by the finish line at Waterfront Brewery\nHalf Marathon start · 7am · Caroline St & Trumbo Rd\n8K start · 7:30am · Same start line; finish behind Waterfront Brewery\nConcert & Awards Party with The Cayo Ritmo Big Band · 8:30am–12:30pm · Outside Half Shell Raw Bar\n8K awards 9:30am · Half Marathon awards 10:30am\nPapa’s Pilar Rum Stroll · 1–5pm · Nine stops from the distillery on Simonton to Southernmost Beach Cafe\nBeach ‘N Beer Mile (untimed; four loops\, four beers) · 3pm · Southernmost Beach Cafe\, 1405 Duval St\nCool Down Pool Party\, free entry · 4–6pm · Blue Flamingo Resort\, 3820 N Roosevelt Blvd\nKey West Farewell Party · 4–6pm · Salty Oyster at the Perry Hotel\, 7001 Shrimp Rd\nAll-day Bloody Mary\, mimosa\, and vodka specials at Half Shell \nMonday\, January 18\nMarathon Farewell Party & Happy Hour · 4–6pm · Blu Bistro at Skipjack Resort & Marina\, 19 Sombrero Blvd\, Marathon \nSchedule subject to change. Information courtesy of the event organizers — see their website for registration\, updates\, and complete details.
URL:https://www.historichideaways.com/event/annual-key-west-half-marathon-5k/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270126
DTEND;VALUE=DATE:20270131
DTSTAMP:20260831T193706Z
CREATED:20230105T192332Z
LAST-MODIFIED:20260831T193706Z
UID:638-1800921600-1801353599@www.historichideaways.com
SUMMARY:Annual Mile 0 Fest Key West
DESCRIPTION:Mile 0 Fest Key West\nJanuary 26–30\, 2027 · Truman Waterfront Amphitheater and venues across the island\n10th Anniversary — Red Dirt\, Americana & Texas Country\nNamed the #1 music festival of 2025 by USA Today\, Mile 0 Fest turns Key West into a five-day music vacation each January. Evening shows run at the Coffee Butler Amphitheater at Truman Waterfront\, while daytime sets spill out across more than ten stages — beaches\, pools\, piers\, bars\, boats\, the historic Key West Theater\, and a few pop-up sets that aren’t on any schedule. Music runs roughly 11am to 11pm daily\, with late-night shows after the amphitheater sets. \n2027 marks the festival’s 10th anniversary\, and organizers are calling it their biggest year yet. New for the anniversary: The Reach Key West joins as a daily venue\, the amphitheater gets upgraded premium viewing and guest amenities\, and more guesthouse buyouts turn additional properties into festival lodging. \n2027 Lineup\nHeadliners include Cross Canadian Ragweed\, Ryan Bingham\, Old Crow Medicine Show\, Wyatt Flores\, and Kaitlin Butts. \nAlso on the bill: Wade Bowen\, 49 Winchester\, William Clark Green\, Stoney LaRue\, American Aquarium\, Tanner Usrey\, Cody Canada and the Departed\, Silverada\, Corb Lund\, Jason Scott & The High Heat\, Taylor Hunnicutt\, Kevin Fowler\, Roger Creager\, Micky & the Motorcars\, The Creekers\, The Jack Wharff Band\, Nicholas Jamerson\, Pony Bradshaw\, The Droptines\, Bri Bagwell\, Courtney Patton\, Adam Hood\, Jamie Lin Wilson\, and Shelby Stone\, among more than fifty artists. \nPasses & Packages\nFull experience packages bundle lodging with festival access and include perks you can’t buy separately — a Tuesday kickoff happy hour\, a private “Songwriter Spotlight” theater show\, and the “Sessions at Sea” live music sail. \n\nPlatinum Premier Package — from $3\,326 per person (based on two) · Sold out\nGold Premier Package — from $2\,683 per person\nPirate Package — from $2\,033 per person\nBeach Bum Package — from $1\,856 per person\nWeekender Package — from $1\,233 per person (three nights\, Thursday–Sunday)\n\nFestival-only passes are also available: \n\nPlatinum VIP Pass — $1\,646 · Sold out\nGold VIP Pass — $1\,175\nBeach Bum Pass — $587\n\nA $50 per-order discount is available through GOVX for military\, first responders\, and law enforcement. Single-day passes are expected to be released closer to the festival. \nGood to Know\nParking near the amphitheater is essentially nonexistent — walk\, bike\, or take a taxi or rideshare. All events run rain or shine. The festival app carries the full daily schedule\, typically posted about 30 days out\, along with set times and pop-up announcements. Mile 0 Fest gives back\, too. In 2026 fans raised more than $55\,000 for the Red Dirt Relief Fund\, Key West Wildlife Center\, and Key West Civic Association\, with signed guitars auctioned nightly. \nSchedule and lineup subject to change. Information courtesy of Mile 0 Fest — see mile0fest.com for packages\, passes\, and complete details. \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:20270213
DTEND;VALUE=DATE:20270215
DTSTAMP:20260706T185504Z
CREATED:20230105T153819Z
LAST-MODIFIED:20260706T185504Z
UID:595-1802476800-1802649599@www.historichideaways.com
SUMMARY:Florida Keys Seafood Festival
DESCRIPTION:Florida Keys Seafood Festival\nFEBRUARY 13-14\, 2027\n\n\nTwo Days of Seafood\, Music & Family Fun!\n\n\nJoin us for the 20th Annual Florida Keys Seafood Festival at Truman Waterfront Park in Key West. For just $10 admission\, enjoy two full days of fresh\, local seafood\, live music\, activities\, and the vibrant island atmosphere that make this festival a Florida Keys favorite. This family-friendly event not only highlights the freshest local catch but also showcases the dedication of our commercial fishermen and women.\n\n\n\n\n\n\n\nOn the Menu…\n\n\n\n\nFried Fish baskets or platters with slaw and black beans & rice\, Fried Shrimp basket\, Grilled Spiny Lobster Platters\, Stone Crab Claws with key lime mustard sauce\, peel and eat Key West Pink Shrimp with cocktail sauce\, Smoked Fish Dip with crackers\, Creamy Lobster Bisque\, Bahamian style Conch Chowder\, Conch Ceviche\, & Conch Fritters. Hot dogs and hamburgers also will be for sale. Beverages include beer\, wine\, rumaritas\, rum runners\, water\, soda and coffees. Desserts include Key Lime Pie and other homemade treats. \nActivities \n\n\n\n\n\nRaffle to win $250 in seafood shipped to your home!\nGreat shopping and art\nFantastic entertainment all day\n\nChildren’s Eco Discovery Zone with activities \n\nAdult beverages\, beer\, wine\, frozen rumaritas with First Legal Rum\nEvent t-shirts\, mugs and authentic lobster trap buoys for sale\n\nThe Florida Keys Seafood Festival directly supports the mission of the Florida Keys Commercial Fishermen’s Association (FKCFA)\, an organization dedicated to protecting\, promoting\, and sustaining the Keys’ commercial fishing community.\n\n\nCREDIT: http://www.floridakeysseafoodfestival.com/ \nInformation / data courtesy of the event organizers. Please visit their link for tickets and updates where applicable. (Information subject to changes and errors and omissions.)
URL:https://www.historichideaways.com/event/florida-keys-seafood-festival/
LOCATION:Truman Waterfront Park\, Key West\, FL\, United States
CATEGORIES:Festivals,Outdoor Activities
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270405
DTEND;VALUE=DATE:20270406
DTSTAMP:20260831T193107Z
CREATED:20230105T194612Z
LAST-MODIFIED:20260831T193107Z
UID:666-1806883200-1806969599@www.historichideaways.com
SUMMARY:Taste of Key West
DESCRIPTION:Taste of Key West\nMonday\, April 5\, 2027 · 6:00–9:00 PM · Truman Waterfront Park\nKey West’s Premier Food & Wine Festival\nKey West’s biggest food and wine night takes over the Truman Waterfront for one evening each spring. Sample your way through dishes from dozens of the island’s best restaurants\, work through curated wines\, craft beers\, and spirits\, and watch the sun go down over the harbor. The event benefits Keys Health and Housing\, which marks 41 years of health\, housing\, and community programs across the Florida Keys in 2027. \nWhat to Expect\nCulinary Excellence — Nearly forty local restaurants participate\, from Duval institutions and waterfront kitchens to food trucks and neighborhood favorites. Past years have included Blue Heaven-era classics alongside newer spots — Bagatelle\, Café Solé\, Garbo’s Grill\, Green Parrot\, Hot Tin Roof\, Latitudes\, Nine One Five\, Square Grouper\, and many more. \nPremium Beverages — Curated wines\, craft beers\, and spirits\, with sommeliers on hand to walk you through the pours. \nWaterfront Views — Three hours of sunset over Key West Harbor from the Truman Waterfront lawn\, with live music throughout. \nTickets\nGeneral Admission — Free entry\, pay as you go\nEvent access is free. Tasting tickets are $1 each (most tastings run 4–6 tickets)\, with a wine or pint glass at $5 and a plate at $5. \nTwo for Taste Pass — $75\nSixty tasting tickets and two commemorative glasses. Built for couples or a pair of friends. \nVIP Pass — $150\nExclusive VIP tent access\, unlimited food and wine tastings\, butler-passed hors d’oeuvres\, a VIP sommelier experience\, a commemorative glass\, and flexible seating in the VIP area. \nPrices as listed by the organizers; confirm current pricing at purchase. \nSchedule subject to change. Information courtesy of Taste of Key West and Keys Health and Housing — see tasteofkeywest.org for tickets and complete details. \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
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/Taste-of-Key-West-2025.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270721
DTEND;VALUE=DATE:20270725
DTSTAMP:20260831T190631Z
CREATED:20230105T195821Z
LAST-MODIFIED:20260831T190631Z
UID:690-1816128000-1816473599@www.historichideaways.com
SUMMARY:Key West Marlin Tournament
DESCRIPTION:46th Annual Key West Marlin Tournament\nJuly 21–24\, 2027 · Key West \nCelebrating 46 years of world-class sportfishing\, the Key West Marlin Tournament returns to Key West July 21–24\, 2027. \nThe tournament coincides with Hemingway Days\, drawing anglers eager to test “The Wall” — the deep blue water off Key West — while the island hosts a week of Hemingway-themed festivities. Crews compete across three fishing days in the Marlin Division for blue marlin\, white marlin\, and spearfish\, with an optional Fun Fish Division for dolphin\, wahoo\, and tuna. Off the water\, the schedule includes the captains meeting\, nightly on-location dinners\, and the awards banquet. \nEntries are limited to the first 75 boats. \nFor reference\, the 2026 tournament paid out $260\,000 in total cash prizes\, including a $50\,000 Marlin Division purse. Prize structure and entry fees for 2027 have not yet been announced. \nThe full 2027 schedule of events\, entry fees\, and prize details will be posted by the organizers as they’re finalized. \nSchedule subject to change. Information courtesy of the Key West Marlin Tournament — see keywestmarlin.com for registration\, the full schedule\, and complete details.
URL:https://www.historichideaways.com/event/key-west-marlin-tournament/
CATEGORIES:Outdoor Activities
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/cropped-key-west-marlin-tournament-logo-512x512-1.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270811
DTEND;VALUE=DATE:20270816
DTSTAMP:20260831T190129Z
CREATED:20230105T211816Z
LAST-MODIFIED:20260831T190129Z
UID:703-1817942400-1818374399@www.historichideaways.com
SUMMARY:Key West Tropical Heat
DESCRIPTION:2027 Dates: 8/11 – 8/15\n\nTropical Heat is the HOTTEST annual 5-day party for gay men ages 21 and up in Key West and the Florida Keys! The all-male themed parties\, pool parties\, clothing optional events\, and adult-oriented entertainment promise to be HOT! August on our tropical island is always HOT\, but during Tropical Heat it promises to be even more so! What better way to experience our tropical paradise than joining us for 5 days with hot guys!? In addition to all our scheduled events\, you can also enjoy our many other activities on land and sea!\n  \n__________________________________________________________________________________________ \n\n\n\nTropical Heat 2026 Schedule of Events\n\n\n\n\n\n\n\n\n\n\n\n\n\n\nWednesday\, August 12th\n\n\n\n5 PM– Cowboy Ken’s PINK Pool Party  AND Kick-off @ Island House  – 1129 Fleming St.\nThink pink at the southernmost mojo-dojo-casa-house! Pink cowboy hats\, pink hankies\, pink speedos\, OR LESS! Just make it PINK! Free appetizers and ½ price cocktails. VIP band holders can also pick up their bands at this events. Bands can also be picked up at the Gay Key West Visitor Center at 808 Duval St. through Tropical Heat between the hours of 9 am and 5 pm. For more info call (305) 294-4603. \n\n\n\n\n\n\n\n\nThursday\, August 13th\n\n\n\n10:30 AM – All Male Day Trip 🏳️‍🌈Ages 18+ • 4 Hours • BYOB *Snorkel\, Sandbar or Kayak on Blu Q \nTrip includes: \n\nAll Male + Clothing Optional\nSnacks & Water Included\, BYOB\nSnorkel & Kayak Gear Included\nCaptains-Choice: activities tailored to the day’s weather conditions. We all want to have an amazing Key West day on the water!\nFree Cancellation up to 6 days (144 hours) prior to scheduled departure time.\nBring a towel\, and feel free to bring your own drinks! Our amazing crew will make sure your drinks stay cold in our coolers. They’re great at keeping track of who brought what and will keep you refreshed all day.\n**Sandbar and Snorkel is our typical day on the water\, but on certain weather and tide days\, it can be tough to go to a sandbar\, so we offer the option to kayak instead.\n\nTickets are available HERE \n\n9:30 PM – Nightly Karaoke at Bobby’s Monkey Bar – 900 Simonton St \nUnpretentious dive bar at 900 Simonton St in Key West (a block off Duval)\, known island-wide as one of the best karaoke spots in town. Karaoke runs nightly from 9:30 until late\, with the place typically just getting going around 10pm and rocking by 11. \n\n10:00 PM – Dancers on The Bar at Bourbon St Pub – 724 Duval St \nThe Bourbon St. Pub has been known all around the world for its Hot Men. And you can catch them each and every night on top of the bar for your viewing pleasure\, starting at 10 PM. \n\n\n\n\n\n\n\n\nFriday\, August 14th\n\n\n\n10:30 AM – Tropical Heat Snorkel Trip @ Blu Q Key West – 120 Margaret St. \nIf you haven’t set sail on Blu Q yet\, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel\, kayak\, swim\, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable\, with their warm smiles\, expert guidance\, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets available HERE \n\n1 PM – 5 PM  Splash Pool Party @ Bourbon St. Pub – 724 Duval St. \nJoin World Famous Puddin’ Tane for some fabulous pool games and get a chance to meet the Adult Stars of Saturday Night’s Big ‘O’ Party while you beat the heat with ice cold drink specials from Key West Pride’s award-winning bartenders! Entrance and free clothes check included with your weekend pass bracelets! $20 or FREE \n\n9PM – 4AM Heat Stroke: Leather Gear and Underwear Party @ Saloon One – 504 Petronia St  \nWhether you’re rocking your favorite leather\, stripped down to your best underwear\, or somewhere in between\, this is your space to let loose\, connect\, and own the night. Expect pulsing beats\, a bold crowd\, and an unapologetically sexy atmosphere. Dress to impress\, or undress to express. \n\n\n\n\n\n\n\n\nSaturday\, August 15th\n\n\n\n10:30 AM–Enjoy a 4-hour Male All Day Trip with Blu Q Key West. \nIf you haven’t set sail on Blu Q yet\, you’re missing out on the best gay experience in Key West! Blu Q guests keep coming back for more and it’s no surprise why. Their four-hour Tropical Heat trip is the perfect way to experience the turquoise waters of Key West while basking in the Florida sun. You can snorkel\, kayak\, swim\, or just relax on the boat – it’s totally up to you! Our crew is always ready to make your trip unforgettable\, with their warm smiles\, expert guidance\, and a hard work ethic. So what are you waiting for? Hop on board the Blu Q and let’s make some memories! This one sells out quickly. Tickets are available HERE \n\n12 PM –Five-Alarm Pool Party@ Island House – 1129 Fleming St \nAll fireman report to the pool deck for this high-energy firefighter themed pool party! Slide down the pole and get ready to get blasted by our pool boy CO2 cannon! Expect hot men & cold cocktails to make the perfect sizzling summer memory with friends! \n\n10 PM – The Big “O” Exhibition @ Bourbon St. Pub – 724 Duval St. \nA Voyeurs Dream Come True! The biggest blow out of the weekend! Foam party. Play areas. Pool & Jacuzzi. Hot Exotic Dancers and Adult Industry Performers. \nLive Exhibition Shows. Free entry with your VIP bands\, or $20 for non pass holders at the door. Free clothes check! \n\n\n\n\n\n\n\n\nSunday\, August 16th\n\n\n\n\n12 PM –Hot Naked Pool Party@ Island House – 1129 Fleming St \nAfter church\, and before T-Dance\, comes Island House! For over two decades\, this party brings visitors and locals together in true Gay Key West spirit! Hot-Naked-FUN! \n\n\n\n\n\n\n\n\nDaily Activities\n\n\n\nMuseums: Ernest Hemingway\, Key West Butterfly Conservatory\, Little White House\, Key West Aquarium\, Mel Fisher Maritime Museum\, Key West Firehouse Museum\, Key West Light House\, Key West Ship Wreck Museum\, Audubon House\, Oldest House and Garden Museum\, USCGC Ingham Museum\, Tennessee Williams Exhibit. \nLand Activities: Key West Food Tours\, Up the Keys Eco Tour\, Fort Zachary State Park\, West Martello Tower\, A & M Scooter Rental\, Key West Tropical Forest and Botanical Garden\, Key West Cemetery\, Key West Adventures\, Papa’s Pilar Rum Distillery\, Ghost Hunt\, Old Town Trolley Tours\, Conch Tour Train\, Haunted Key West\, Ghosts and Mysteries\, Ghosts and Gravestones\, D’vine Wine Gallery\, Perky’s Key West Excursions. \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. Land Boat Charters\, Off the Charts\, Schooner America\, Sunset Sail Key West\, Sunset Watersports\, SV Argo Navis\, Yankee Freedom.
URL:https://www.historichideaways.com/event/key-west-tropical-heat/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals,Outdoor Activities
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DTSTART;VALUE=DATE:20270811
DTEND;VALUE=DATE:20270816
DTSTAMP:20260831T190312Z
CREATED:20230105T212024Z
LAST-MODIFIED:20260831T190312Z
UID:706-1817942400-1818374399@www.historichideaways.com
SUMMARY:Key West Lobsterfest
DESCRIPTION:Mark your calendars! We are already looking ahead and can’t wait to do it all over again. Please join us for the 29th Annual Key West Lobsterfest\, taking place August 11–15\, 2027.\n______________________________________________________________________\nGet Ready to Crack! Key West Lobsterfest 2026 Dates are Set!\n\nThe wait is officially over! Get your butter warmers ready because we are thrilled to announce the dates for the biggest and tastiest summer celebration on the island: Key West Lobsterfest 2026 is happening from Wednesday\, August 5th through Sunday\, August 9th! \nJoin us for five unforgettable days as we celebrate the opening of the Florida Spiny Lobster season with an island-wide party. From the savory kickoff Lobster Boil to the massive Duval Street Fair with live music and endless crustaceans prepared every way imaginable\, this is the ultimate crustacean celebration. \n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n\n \nHistory of Key West Lobsterfest\n\n\n\nBorn from a Brawl (Over Lobster\, No Less!)\n\n Believe it or not\, Key West Lobsterfest started with a friendly (or maybe not-so-friendly) dispute. Two friends couldn’t agree on who made the best Lobster Chilau\, a Key West staple. What else to do but settle it with a cook-off? The inaugural throwdown went down in the courtyard of Rick’s & Durty Harry’s Entertainment Complex\, with secret family recipes and judges galore. The event was such a hit (though we’ll keep the winner a secret)\, they knew they had to take it bigger. The next year\, Lobsterfest moved to the bustling Duval Street\, welcoming more participants\, spectators\, and sponsors than ever before. Fast forward to today\, and this epic food fight has transformed into a 4-day extravaganza that takes over the entire island! \n\nKEY WEST LOBSTERFEST 2026 28th Annual\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.)\nWEDNESDAY\, AUGUST 5 \n6:00 PM – 9:00 PM Key West Lobsterfest Kick-Off Party Rick’s & Durty Harry’s Entertainment Complex 202 Duval Street\, Historic Old Town \nHome of the inaugural Lobsterfest — this is where it all began with a contest for the best lobster dish on the island. Join us to kick off the 28th Annual Key West Lobsterfest. We need to empty the freezers to make room for freshly caught lobster! \nEnjoy amazing lobster pizza and drink specials featuring our Official Sponsors Sun Cruiser Iced Tea and Cuervo 1800 Tequila. \n\nTHURSDAY\, AUGUST 6 \n6:00 PM – 9:00 PM Lobster Boil at The Porter Mansion Courtyard – 429 Caroline Street\, Historic Old Town \nJoin us for our annual seafood lobster boil in a beautiful Key West setting with a full bar\, music\, and delicious food. \n\nFresh lobsters\nJumbo Key West shrimp\nRed skin potatoes\nFresh corn on the cob\nFresh baked jalapeño corn bread & melted butter\n\nEach ticket is good for one guest’s admission and meal. \n\nFRIDAY\, AUGUST 7 \n3:00 PM – 6:00 PM Pool Party at The Marker Resort – Key West Harbor Resort – 200 William Street \nFree Admission – Relax and soak up the fun. \n8:00 PM – Midnight Lobsterfest Duval Pub Crawl Check-in: The Marker Resort Pool Bar\, 200 William Street \nJoin us for the 28th Annual Lobsterfest Pub Crawl! The fun starts immediately after sunset and goes until midnight. \nWhat’s included: \n\nOfficial Lobsterfest T-shirt\nSouvenir lanyard\nAmazing drink specials on Sun Cruiser Iced Tea and Cuervo 1800 Tequila at participating bars\n\nTickets: $25 in advance / $30 at the door. A portion of proceeds benefit the Key West High School Scholarship Fund. Pick up your T-shirt\, lanyard\, and crawl instructions at the Marker Resort Pool Bar on August 7th from 3:00 PM – 7:30 PM. All items must be picked up in person. \n\nSATURDAY\, AUGUST 8 \nNoon – 11:00 PM – Street Fair & Concert 100–500 Blocks of Duval Street – Free Admission \nArts & crafts\, merchandise\, and more lining Duval Street all day. \nLocal bars and restaurants will be serving fresh Florida Lobster — everything from appetizers to full meals. No entrance fee; food and drinks sold individually. \nLocal bars will also be set up on Duval Street featuring ice-cold Corona\, Blue Chair Bay Rum cocktails\, and more. \nLive Music Lineup: \n1:00 PM Just George – Duval St. & Greene St. \n3:00 PM Fried Newt – Main Stage \n5:30 PM Jordan Oaks – Main Stage \n8:00 PM The Durtbags – Main Stage — then continuing late night at Durty Harry’s
URL:https://www.historichideaways.com/event/key-west-lobsterfest/
CATEGORIES:Festivals,Outdoor Activities
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