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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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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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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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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261112T080000
DTEND;TZID=America/New_York:20261114T170000
DTSTAMP:20260905T201850Z
CREATED:20260905T201850Z
LAST-MODIFIED:20260905T201850Z
UID:3346-1794470400-1794675600@www.historichideaways.com
SUMMARY:Destroying David
DESCRIPTION:November 12 – 14\, 2026\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront Playhouse launches its Spotlight Series with the Florida premiere of \, a solo play written by Jason Odell Williams. It runs about 75 minutes and takes the form of a private tour of Michelangelo’s David at the Galleria dell’Accademia in Florence\, led by a guide who walks the audience through the statue’s history and its surprisingly precarious physical condition. As the tour goes on\, the guide’s real reason for arranging it comes into focus. The play has been described as funny\, heartbreaking\, and ultimately uplifting\, and it’s built around the question of what art is for — why we preserve certain objects\, and what they can do for us in bad moments. \nThe Waterfront’s production is part of the new Spotlight Series\, with three performances only. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/destroying-david/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20261122
DTEND;VALUE=DATE:20261123
DTSTAMP:20260905T205346Z
CREATED:20260905T205346Z
LAST-MODIFIED:20260905T205346Z
UID:3370-1795305600-1795391999@www.historichideaways.com
SUMMARY:The Buena Vista Orchestra
DESCRIPTION:Sunday\, November 22\, 2026\nKey West Theater\, 512 Eaton Street \nThe Buena Vista Orchestra comes to the Key West Theater\, billed by its presenter as the world’s foremost Cuban music repertory ensemble. The group works with a revolving lineup drawn from the original Buena Vista Social Club performances and from the bands of Celia Cruz\, Omara Portuondo\, Chucho Valdés\, Willie Colón\, and the AfroCuban All Stars. \nRecent touring lineups have been led by Cuban violinist Rolando Morejón Reyes\, whose credits include the Orquesta de Enrique Jorrín and the bands of Omara Portuondo\, Willie Colón\, Cachao López\, and Oscar D’León. He has been joined by trumpeter Antonio Perigo\, pianist Helder Rojas\, trombonist Yosmel Garcerarn\, and percussionists Miguel Valdés and Pepe Espinosa\, among others. \nBetween the Buena Vista Social Club\, the Buena Vista Orchestra\, and their related projects\, this is the best-known and biggest-selling Cuban music enterprise on record\, with documentaries and stage productions built around it. The tour is presented by SSK Music. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-buena-vista-orchestra/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261202T080000
DTEND;TZID=America/New_York:20261217T170000
DTSTAMP:20260905T202155Z
CREATED:20260905T202155Z
LAST-MODIFIED:20260905T202155Z
UID:3349-1796198400-1797526800@www.historichideaways.com
SUMMARY:It's a Wonderful Life: A Live Radio Play
DESCRIPTION:December 2 – 17\, 2026\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront Playhouse’s holiday show turns the theatre into a 1940s radio studio for It’s a Wonderful Life: A Live Radio Play\, Joe Landry’s adaptation of the Frank Capra film. A small cast plays every role\, performing the story live at microphones the way a radio drama would have been broadcast in the era. \nThe production includes live Foley effects created onstage\, a jazz trio\, and original jingles written for local Key West businesses — the commercial breaks a 1940s broadcast would have carried\, rewritten for here. \nThe story is the familiar one: George Bailey\, a run of bad luck\, and an angel named Clarence sent to show him what Bedford Falls would look like if he’d never been born. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/its-a-wonderful-life-a-live-radio-play/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20261208T080000
DTEND;TZID=America/New_York:20270102T170000
DTSTAMP:20260905T200354Z
CREATED:20260905T200354Z
LAST-MODIFIED:20260905T200354Z
UID:3332-1796716800-1798909200@www.historichideaways.com
SUMMARY:Shooting Star
DESCRIPTION:December 8\, 2026 – January 2\, 2027 · Shows at 7:00pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn opens its holiday slot with Shooting Star\, a two-hander by Steven Dietz\, one of the most widely produced playwrights working in American theater. The setup is simple enough to describe in a sentence: two people who were together in college get snowed in overnight at a middling airport in the middle of the country and find themselves face to face for the first time in years. \nWhat follows is the whole play — no scene changes\, no third character\, nowhere for either of them to go. They talk. They avoid talking. They circle the years between then and now\, the versions of themselves the other still half-expects\, and the question of what they actually meant to each other. Dietz keeps it funny throughout\, and the comedy does most of the heavy lifting until it quietly stops being only funny. \nThe Red Barn production stars Dave Bootle and Lauren Thompson\, with Joy Hawkins directing. It’s ideal material for a house this size — the Red Barn seats fewer than a hundred\, and a play built entirely on two people reading each other across a row of airport chairs lands very differently at close range. Several extra Monday performances have been added over the holidays. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/shooting-star/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270107T080000
DTEND;TZID=America/New_York:20270109T170000
DTSTAMP:20260905T202454Z
CREATED:20260905T202454Z
LAST-MODIFIED:20260905T202454Z
UID:3352-1799308800-1799514000@www.historichideaways.com
SUMMARY:Blanche and Beyond
DESCRIPTION:January 7 – 9\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Spotlight Series continues with Blanche and Beyond\, Steve Lawson’s one-man play assembled from Tennessee Williams’s own letters. It’s the sequel to Lawson’s A Distant Country Called Youth\, which drew on the early correspondence; this one covers 1945 through 1957\, the stretch that produced A Streetcar Named Desire\, Summer and Smoke\, The Rose Tattoo\, and Cat on a Hot Tin Roof. \n \nThe letters are by turns funny\, obscene\, and unguarded\, and they catch Williams in the middle of something he never quite adjusted to — going from unknown to internationally famous in the space of a few years. He writes about Brando\, Jessica Tandy\, Elia Kazan\, David O. Selznick\, Laurence Olivier\, and Vivien Leigh\, and about the plays still forming in his head. \nWilliams was living in Key West through most of the years these letters cover. He bought the Duncan Street house in the late 1940s and kept it until his death. \nBlanche and Beyond opened the Tennessee Williams New Orleans Literary Festival in 2006\, in a production directed by Lawson and performed by Richard Thomas. Three performances only in Key West. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/blanche-and-beyond/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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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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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270118
DTEND;VALUE=DATE:20270119
DTSTAMP:20260905T192050Z
CREATED:20260905T192050Z
LAST-MODIFIED:20260905T192050Z
UID:3309-1800230400-1800316799@www.historichideaways.com
SUMMARY:The Doo Wop Project
DESCRIPTION:Monday\, January 18\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nAmerica’s premiere doo wop group brings a brand-new show to the Tennessee Williams Theatre stage this January. The Doo Wop Project takes today’s biggest hits and “doowop-ifies” them — reimagining contemporary songs as though they’d been written and recorded in 1958. Familiar melodies arrive wrapped in tight harmony\, walking bass lines\, and finger-snap rhythm\, and the effect is genuinely surprising the first time you hear a modern radio staple come at you in a completely different decade. It’s the reason audiences around the country leave these shows talking\, and the reason the group has built a following well beyond the generation that grew up with the original records. \nAn evening at the Tennessee Williams Theatre is one of the more comfortable nights out in Key West — a proper 480-seat house on the College of the Florida Keys campus\, with easy free parking\, which is not something you can say about most venues on this island. Subscription packages covering the full 2027 season are available at a 15% savings if you’re planning to catch more than one show. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-doo-wop-project/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Concerts,Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270119T080000
DTEND;TZID=America/New_York:20270220T170000
DTSTAMP:20260905T200725Z
CREATED:20260905T200725Z
LAST-MODIFIED:20260905T200725Z
UID:3336-1800345600-1803142800@www.historichideaways.com
SUMMARY:Dracula: A Comedy of Terrors
DESCRIPTION:January 19 – February 20\, 2027 · Tuesdays–Saturdays at 7:30pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn follows its holiday show with Dracula: A Comedy of Terrors\, the Gordon Greenberg and Steve Rosen send-up that became an off-Broadway hit and has been working its way through regional theaters ever since. The premise is the Bram Stoker story you already know\, played entirely for laughs — a high-camp spoof that borrows its sensibility about equally from Mel Brooks and Monty Python and never slows down long enough for anyone to take it seriously. \nThe whole thing runs on a small cast covering a great many characters\, with gender-bent casting\, quick changes\, and a fair amount of deliberate chaos. Jokes land at a clip\, the physical comedy is broad on purpose\, and the script is happy to break its own logic if there’s a bigger laugh available. If you’ve seen the Red Barn take on this kind of material before\, you know they commit. \nThe Key West production stars Jody Orrigo\, Susannah Wells\, Erin McKenna\, Phillip Cole White\, and Dominic Paolillo\, directed by Mimi McDonald. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/dracula-a-comedy-of-terrors/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270121
DTEND;VALUE=DATE:20270122
DTSTAMP:20260905T193128Z
CREATED:20260905T193128Z
LAST-MODIFIED:20260905T193128Z
UID:3312-1800489600-1800575999@www.historichideaways.com
SUMMARY:NoGravity Theatre
DESCRIPTION:Thursday\, January 21\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nOne of Italy’s most inventive performing arts companies makes a stop in Key West this January. NoGravity was founded in Rome in 2005 by artist Emiliano Pellisari\, and it has spent two decades building a form of theater that doesn’t fit neatly into any existing category — part dance\, part visual art\, part outright illusion. Bodies appear to float\, fall upward\, and dissolve into one another. The mechanics behind it are never explained and\, honestly\, are better left unexplained. \nThe company draws its imagery from the Italian Renaissance and Baroque\, translating the compositions of old master painting into moving bodies on a darkened stage. The result is dreamlike rather than technical — surreal tableaux that assemble\, hold for a beat\, and come apart. Since 2010 the dance cast has been led by Mariana Porceddu\, a graduate of the National Academy of Dance who became co-author of the company’s choreography in 2012. \nNoGravity performs annually in major Italian theaters and tours internationally with support from Italy’s Ministry of Cultural Heritage. This is the kind of production that rarely makes it this far south\, and it’s worth seeing on a proper stage rather than in a clip.
URL:https://www.historichideaways.com/event/nogravity-theatre/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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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:20270127
DTEND;VALUE=DATE:20270201
DTSTAMP:20260831T184548Z
CREATED:20230105T192722Z
LAST-MODIFIED:20260831T184548Z
UID:642-1801008000-1801439999@www.historichideaways.com
SUMMARY:Key West Food and Wine Festival
DESCRIPTION:2027 Key West Food and Wine Festival\nJanuary 27–31\, 2027 \n5 continents ~ 5 wines ~ 5 stories ~ 5 dishes ~ 5 chefs \nWelcome to Key West Food & Wine Festival 2027\nA curated journey through the culinary heritage of five continents\, featuring world-renowned chefs\, their signature dishes\, and the legendary wines that define their regions. \nThis journey spans five continents with iconic wines\, each telling a story of terroir\, history\, and culture: \n\nAfrica: a smoky Pinotage\nEurope: a structured Bordeaux\nSouth America: a robust Malbec from Mendoza\nOceania: a vibrant Marlborough Sauvignon Blanc\nNorth America: a cool-climate Pinot Noir from Oregon\n\nThe Key West Food and Wine Festival is recognized as one of the best food and wine festivals in the country by the Travel Channel. If you’re a foodie\, Key West is the place to be in January. With many unique events\, held at spectacular island locations\, this is an opportunity to enjoy a wide variety of wines and cuisine\, with waterfront tastings\, wine/food pairings\, and local events around Key West. \nAt a Glance\nWednesday\, January 27 — Welcome to the Festival\nVIP Welcome Party · 5–7pm · Realty One Group Destination\, 1075 Duval St \nThursday\, January 28 — Around the World\nThe Wine Game\, a tasting challenge · 11am–1pm · Key West Cooking Show\, 291 Front St\nWelcome to Oceania: Island Flavors Dinner with Chef Dave Fuhrman · 6–9pm · Audubon House & Tropical Garden\, 205 Whitehead St \nFriday\, January 29 — Europe & North America\nHidden Gems & Golden Sips · 1:30–4pm · Trolley departs Gardens Hotel\, 526 Angela St\nFive Continents Grand Tasting · 6–8pm · Key West Aquarium\, 1 Whitehead St\nAn Exclusive Celebration of American Spirit · 7–10pm · Truman Little White House\, 111 Front St \nSaturday\, January 30 — Key West\, North America & South Africa\nCooking with Love: The Saturday Kitchen Party · 8:45–10am · 1215 Petronia St\n“A Dream Come True” · 12–2pm · Venue TBA\nWelcome to South Africa: Lost Kitchen Supper Club · 6–9pm · Trolley pick-up 5:45pm \nSunday\, January 31 — Europe\nPranzo on the Amalfi Coast · 12–2pm · Conchiglia Key West\, 816 Duval St \nSchedule subject to change. Information courtesy of the Key West Food & Wine Festival — see their website for tickets\, updates\, and complete details.
URL:https://www.historichideaways.com/event/key-west-food-and-wine-festival/
LOCATION:Key West\, Florida\, Key West\, FL\, 33040\, United States
CATEGORIES:Festivals
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/wine_glass_0.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270128T080000
DTEND;TZID=America/New_York:20270206T170000
DTSTAMP:20260905T202701Z
CREATED:20260905T202701Z
LAST-MODIFIED:20260905T202701Z
UID:3355-1801123200-1801933200@www.historichideaways.com
SUMMARY:Unnecessary Farce
DESCRIPTION:January 28 – February 6\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage returns to Paul Slade Smith\, whose The Angel Next Door played there previously\, with Unnecessary Farce. Two cops have set up a sting in a cheap motel\, hoping to catch the mayor taking a bribe. There are two adjoining rooms\, a video camera pointed at the wrong one\, an accountant\, three crooks\, a Scottish hit man\, and eight doors. \nSmith’s play premiered in 2006 and has since become one of the most frequently produced comedies in American regional theater\, largely on the strength of its construction — the plot is engineered so that every escalation follows logically from the last\, however absurd things get. \nReviewers have called it the funniest thing they’d seen in years\, and credited Smith with making the in-one-door\, out-the-other machinery feel new again. It runs about two hours. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/unnecessary-farce/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270201
DTEND;VALUE=DATE:20270202
DTSTAMP:20260905T193433Z
CREATED:20260905T193433Z
LAST-MODIFIED:20260905T193433Z
UID:3315-1801440000-1801526399@www.historichideaways.com
SUMMARY:The Pirates of Penzance
DESCRIPTION:Monday\, February 1\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nThe New York Gilbert & Sullivan Players bring their production of  to Key West this February. NYGASP has been the country’s leading Gilbert & Sullivan repertory company for more than fifty years\, and Pirates is the piece they’re best known for — a full staging with orchestra\, chorus\, and the kind of comic timing that only comes from performing the same material for decades without getting tired of it. \nThe plot runs on one of Gilbert’s better absurdities. Frederic has been apprenticed to a band of soft-hearted pirates and intends to leave their service on his twenty-first birthday to devote himself to stamping out piracy. The catch is that he was born on February 29th\, which means his twenty-first birthday won’t arrive until 1940. Duty being duty\, he goes back to the pirates. What follows involves a false claim of orphanhood\, a squad of thoroughly reluctant policemen\, and a resolution that hinges on everyone turning out to be a nobleman. Along the way you get “I Am the Very Model of a Modern Major-General\,” still the most famous patter song ever written and still\, done well\, genuinely funny. \nThe New York Times has praised the company’s staging as opulent and inventive\, singling out the chorus of pirates\, daughters\, and policemen and the strength of the orchestra. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-pirates-of-penzance/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270209
DTEND;VALUE=DATE:20270210
DTSTAMP:20260905T193730Z
CREATED:20260905T193730Z
LAST-MODIFIED:20260905T193730Z
UID:3318-1802131200-1802217599@www.historichideaways.com
SUMMARY:Afrique en Cirque
DESCRIPTION:Tuesday\, February 9\, 2027\nDoors 5:30pm\, Show 6:30pm · Tennessee Williams Theatre \nAfrique en Cirque comes to Key West as part of the Tennessee Williams Theatre’s new Family Fun Series\, a slate of shows programmed for audiences of all ages. It’s the signature production of Cirque Kalabanté\, the company founded by Guinean acrobat Yamoussa Bangoura\, and it draws directly on the daily life\, movement\, and music he grew up with in Guinea. \nThe show pairs high-level acrobatics with live music rather than a recorded score. Performers build human pyramids\, tumble\, and work the Cyr wheel while a band plays Afro-jazz built around percussion and the kora\, the twenty-one-string West African harp that gives the music its distinctive rippling sound. There’s no elaborate set to hide behind — the appeal is bodies\, rhythm\, and a company of young performers doing genuinely difficult things a few feet from the audience. \nIt’s a good fit for families\, and the earlier curtain reflects that: doors at 5:30 and a 6:30 start rather than the theatre’s usual 7:30. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/afrique-en-cirque/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270211
DTEND;VALUE=DATE:20270212
DTSTAMP:20260905T205649Z
CREATED:20260905T205649Z
LAST-MODIFIED:20260905T205649Z
UID:3374-1802304000-1802390399@www.historichideaways.com
SUMMARY:Who's Bad
DESCRIPTION:Thursday\, February 11\, 2027\nKey West Theater\, 512 Eaton Street \nWho’s Bad brings its Michael Jackson tribute to the Key West Theater. The group has been at this since 2003 and has logged more than 2\,500 performances — theaters\, clubs\, festivals\, and House of Blues rooms across the U.S.\, plus tours through the U.K.\, China\, Thailand\, Mexico\, Canada\, Germany\, and the Gulf states\, including a run at London’s O2 Arena. \nThe band’s stated approach is re-creation rather than impersonation: a live cast of musicians and dancers\, drawn from backgrounds including Broadway and Super Bowl halftime shows\, working through the grooves\, vocal inflections\, and choreography rather than miming them. Taalib York fronts the group. \nWho’s Bad has shared stages with Aretha Franklin\, the Four Tops\, Boyz II Men\, the Backstreet Boys\, and Pitbull. Michael Jackson’s longtime manager Frank DiLeo said after seeing the show that Michael would have been proud. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/whos-bad/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/uploadedimage-jpg_6a91bf8471096.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270211T080000
DTEND;TZID=America/New_York:20270213T170000
DTSTAMP:20260905T203003Z
CREATED:20260905T203003Z
LAST-MODIFIED:20260905T203003Z
UID:3358-1802332800-1802538000@www.historichideaways.com
SUMMARY:Call Me Elizabeth
DESCRIPTION:February 11 – 13\, 2027 \nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Spotlight Series continues with the Florida premiere of Call Me Elizabeth\, written and performed by Kayla Boye. It’s set on a single morning in May 1961 at the Beverly Hills Hotel\, drawn from Elizabeth Taylor’s real conversations with the writer Max Lerner about a biography he planned to write. Lerner is never seen — the audience occupies his chair. \n \nTaylor has just won the Academy Award for Butterfield 8\, a film she thought little of\, and is still recovering from the bout of pneumonia that nearly killed her. Over the course of the morning she works through her early life\, her marriages\, her films\, and the gap between the woman she is and the one the fan magazines have invented. The compassion that would later make her one of the first major public figures to take up the fight against AIDS is visible throughout. \nBoye is a Chicago-based actor whose credits include Chicago Shakespeare Theater\, Drury Lane\, and Porchlight Music Theatre; Call Me Elizabeth was her first play. It premiered virtually through the Edinburgh Festival Fringe during the pandemic before its live world premiere at the 2022 Hollywood Fringe Festival\, and has toured since. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/call-me-elizabeth/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/OTSPoster_1800x2700_Elizabeth_26-27-scaled-1.jpeg
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
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2023/01/keywestshrimp.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270227
DTEND;VALUE=DATE:20270228
DTSTAMP:20260905T194427Z
CREATED:20260905T194427Z
LAST-MODIFIED:20260905T194427Z
UID:3321-1803686400-1803772799@www.historichideaways.com
SUMMARY:Ailey II
DESCRIPTION:Saturday\, February 27\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nAiley II is the junior company of Alvin Ailey American Dance Theater\, and calling it a training ensemble undersells it considerably. Founded in 1974 as the Alvin Ailey Repertory Ensemble\, it exists to pair the strongest early-career dancers in the country with choreographers who are themselves still building their reputations. The result is a company with the technical polish of a major troupe and none of the caution — these are dancers with everything to prove\, performing work that hasn’t yet settled into repertory. \n \nPhoto by Nir Arieli and Danica Paulos\, courtesy of Ailey II\nSylvia Waters\, chosen by Alvin Ailey himself as founding artistic director\, led the company through its first thirty-eight seasons and built it into one of the most popular touring ensembles in American dance. Francesca Harper directs it today. Recent programs have included Rena Butler’s In Session and Judith Jamison’s Divining\, mixing new commissions with pieces drawn from the Ailey legacy. \nThe company tours widely but doesn’t often come this far down the Keys. Dance Magazine has called Ailey II second to none\, and The New York Times has described an evening with the company as its own distinct experience\, separate from the parent troupe. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/ailey-ii/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2026/09/AileyIIinRenaButlersInSession.PhotobyNirArieli_1318.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270302T080000
DTEND;TZID=America/New_York:20270320T170000
DTSTAMP:20260905T201141Z
CREATED:20260905T201141Z
LAST-MODIFIED:20260905T201141Z
UID:3339-1803974400-1805562000@www.historichideaways.com
SUMMARY:Liberation
DESCRIPTION:March 2 – 20\, 2027 · Tuesdays–Saturdays at 7:30pm\nRed Barn Theatre\, 319 Duval Street (rear) \nThe Red Barn stages Bess Wohl’s Liberation\, winner of the 2026 Pulitzer Prize for Drama and Best Play at the 2026 Tony Awards. Developed by Roundabout Theatre Company\, it premiered off-Broadway in February 2025 and transferred to Broadway that October\, running through February 2026. \nIt’s a memory play set in two times at once. In 1970\, in the basement of an Ohio rec center\, a woman named Lizzie gathers a small group of women to talk. Fifty years later her daughter looks back\, trying to understand who her mother was before she became her mother. The daughter narrates directly to the audience\, moving the play between past and present. \nThe Pulitzer board cited the play for exploring how the women’s movement grew out of conversation. Wohl’s other work includes Grand Horizons\, Small Mouth Sounds\, and Camp Siegfried. \nThe Red Barn production is directed by Joy Hawkins and features Morgan Fraga Pierson\, Lauren Thompson\, Cassidy Timms\, Fritzie Estimond\, Jessica Miano Kruel\, Ivy Munnerlyn\, Shannon Edwards\, and Jack McDonald. \nSchedule subject to change. Information courtesy of Red Barn Theatre — visit redbarntheatre.com for tickets and complete details.
URL:https://www.historichideaways.com/event/liberation/
LOCATION:Red Barn Theatre\, 319 Duval Street - Rear\, Key West\, Florida\, 33040
CATEGORIES:Theater
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2026/09/Liberation_logo_1200x630.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;TZID=America/New_York:20270304T080000
DTEND;TZID=America/New_York:20270320T170000
DTSTAMP:20260905T203412Z
CREATED:20260905T203412Z
LAST-MODIFIED:20260905T203412Z
UID:3361-1804147200-1805562000@www.historichideaways.com
SUMMARY:Come From Away
DESCRIPTION:March 4 – 20\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage series presents Come From Away\, the musical by Irene Sankoff and David Hein about what happened in Gander\, Newfoundland\, on September 11\, 2001. When American airspace closed that morning\, 38 planes were diverted to Gander’s airport\, and a town of about 9\,000 people took in nearly 7\,000 strangers for the better part of a week. \n \nThe show is built from interviews the writers conducted with Gander residents and the passengers who ended up there. A cast of twelve plays both the townspeople and the travelers\, switching between them onstage\, and the score draws on Newfoundland folk music — fiddle\, accordion\, bodhrán\, Irish flute. It runs about 100 minutes with no intermission. \nCome From Away opened on Broadway in 2017 and ran for five years\, earning seven Tony nominations and a win for Christopher Ashley’s direction. It is about a terrible day\, but it is not really about the attacks; it’s about what a small place did in the days that followed. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/come-from-away/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/OTSPoster_1800x2700_ComeFromAway_26-27-scaled-1.jpeg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270313
DTEND;VALUE=DATE:20270314
DTSTAMP:20260905T210046Z
CREATED:20260905T210046Z
LAST-MODIFIED:20260905T210046Z
UID:3380-1804896000-1804982399@www.historichideaways.com
SUMMARY:Elton Dan & The Rocket Band
DESCRIPTION:Saturday\, March 13\, 2027\nKey West Theater\, 512 Eaton Street \nElton Dan & The Rocket Band bring their Elton John tribute to the Key West Theater. The band formed in 2015 and has since played more than 700 shows across 38 states\, including a crowd of 18\,000 at Kool Deadwood Nights in South Dakota in 2024 and a sold-out night at the Wynn Palace in Macau. \nThe set draws from the run of albums Elton John released across the 1970s and 80s. Expect “Rocket Man\,” “Crocodile Rock\,” “Philadelphia Freedom\,” “The Bitch Is Back\,” and “I’m Still Standing\,” with deep cuts and band favorites like “Levon\,” “Tiny Dancer\,” “Madman Across the Water\,” and “Pinball Wizard” turning up as well\, plus the occasional duet. \nDan’s piano playing carries the show\, along with the costumes. The band’s pitch is a room full of people who came to sing along\, and they play to that. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/elton-dan-the-rocket-band/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
ATTACH;FMTTYPE=image/jpeg:https://www.historichideaways.com/wp-content/uploads/2026/09/uploadedimage-jpg_6a873b511b837.jpg
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270316
DTEND;VALUE=DATE:20270317
DTSTAMP:20260905T195643Z
CREATED:20260905T195022Z
LAST-MODIFIED:20260905T195643Z
UID:3324-1805155200-1805241599@www.historichideaways.com
SUMMARY:Celtic Angels Ireland
DESCRIPTION:Tuesday\, March 16\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nCeltic Angels Ireland arrives in Key West on the eve of St. Patrick’s Day with a full-scale production built around traditional and contemporary Irish music. The show is assembled by a creative team based in Ireland and cast with award-winning and World Champion singers\, dancers\, and musicians\, and it moves through more than thirty tunes over the course of the evening. \nThe vocal ensemble at the center of it — the Celtic Angels themselves — handle the close harmony work that gives the show its name. Around them\, the Celtic Knights Dancers bring the percussive step dancing the tradition is known for\, and the Trinity Ensemble plays everything live. No backing tracks\, which matters more in this repertoire than in most; the fiddle and whistle lines are half the point. \nThe program swings between registers the way Irish music tends to — laments and emigration songs on one side\, reels and set pieces on the other\, often within a few minutes of each other. It’s a good family show and an easy one to bring people to who don’t think they have an opinion about Irish music. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/3324/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Arts,Theater
ATTACH;FMTTYPE=image/webp:https://www.historichideaways.com/wp-content/uploads/2026/09/CAILogoFinal.webp
END:VEVENT
BEGIN:VEVENT
DTSTART;VALUE=DATE:20270319
DTEND;VALUE=DATE:20270320
DTSTAMP:20260905T205842Z
CREATED:20260905T205842Z
LAST-MODIFIED:20260905T205842Z
UID:3377-1805414400-1805500799@www.historichideaways.com
SUMMARY:The Linda Ronstadt Experience
DESCRIPTION:Friday\, March 19\, 2027\nKey West Theater\, 512 Eaton Street \nThe Linda Ronstadt Experience brings its tribute concert to the Key West Theater\, fronted by American Idol alum Tristan McIntosh and backed by a full band. The show focuses on Ronstadt at the peak of her career\, when she was the biggest-selling female recording artist in the country. \nThe set covers the chart singles — “You’re No Good\,” “When Will I Be Loved\,” “That’ll Be the Day\,” “Blue Bayou” — along with songs Ronstadt made famous by Jackson Browne\, Elvis Costello\, Tom Petty\, Neil Young\, Warren Zevon\, and the Rolling Stones. Ronstadt’s gift as an interpreter was picking material from writers who hadn’t broken through yet and turning their songs into hits\, and the show leans into that range. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/the-linda-ronstadt-experience/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270329
DTEND;VALUE=DATE:20270330
DTSTAMP:20260905T195529Z
CREATED:20260905T195529Z
LAST-MODIFIED:20260905T195529Z
UID:3328-1806278400-1806364799@www.historichideaways.com
SUMMARY:Legally Blonde the Musical
DESCRIPTION:Monday\, March 29\, 2027\nDoors 6:30pm\, Show 7:30pm · Tennessee Williams Theatre \nThe Broadway national tour of Legally Blonde the Musical stops in Key West this spring. Adapted from the 2001 film\, the stage version arrived on Broadway in 2007 with music and lyrics by Laurence O’Keefe and Nell Benjamin and a book by Heather Hach\, and it went on to win a fistful of Olivier Awards in London. It has been a staple of touring theater ever since\, largely because it does what it sets out to do without apologizing for any of it. \nElle Woods gets dumped by a boyfriend headed to Harvard Law who has decided he needs someone more serious. Elle follows him there\, talks her way in\, and spends the rest of the show discovering that she is considerably sharper than anyone — including herself — had assumed. The pace is relentless\, the choreography is athletic\, and the score runs from bubblegum to something closer to genuine feeling in “So Much Better” and the title song. Bruiser the chihuahua appears\, as required by law. \nIt holds up better than its reputation suggests. Underneath the pink there’s a real story about being underestimated and deciding not to accept it\, and the show is smart enough to let the joke land without ever making Elle the punchline. Good pick for a mixed group\, and a reliable crowd-pleaser for anyone bringing teenagers. Subscription packages covering the full 2027 season are available at a 15% savings. \nSchedule subject to change. Information courtesy of Tennessee Williams Theatre — visit twstages.com for tickets and complete details.
URL:https://www.historichideaways.com/event/legally-blonde-the-musical/
LOCATION:Tennessee Williams Theatre\, 5901 College Road\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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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
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DTSTART;TZID=America/New_York:20270408T080000
DTEND;TZID=America/New_York:20270417T170000
DTSTAMP:20260905T204125Z
CREATED:20260905T204125Z
LAST-MODIFIED:20260905T204125Z
UID:3364-1807171200-1807981200@www.historichideaways.com
SUMMARY:Dial M for Murder
DESCRIPTION:April 8 – 17\, 2027\nWaterfront Playhouse\, Mallory Square\, 407 Wall Street \nThe Waterfront’s mainstage season concludes with Dial M for Murder\, Frederick Knott’s 1952 thriller in Jeffrey Hatcher’s 2022 adaptation. A husband decides his wealthy wife is worth more to him dead\, and sets out to arrange the perfect murder. What follows is a cat-and-mouse game between him\, his wife\, her lover\, and a police inspector who keeps noticing the small things that don’t add up. \nHatcher’s version\, commissioned by the Old Globe in San Diego\, keeps the 1950s London setting and Knott’s clockwork plotting while reshaping the central triangle and adding a few turns of its own. \nThe Waterfront positions it alongside Wait Until Dark and Accomplice\, both audience favorites at the theatre — tightly built thrillers where the tension comes from watching people think. \nSchedule subject to change. Information courtesy of Waterfront Playhouse — visit waterfrontplayhouse.org for tickets and complete details.
URL:https://www.historichideaways.com/event/dial-m-for-murder/
LOCATION:Waterfront Playhouse\, 407 Wall Street\, Key West\, FL\, 33040\, United States
CATEGORIES:Theater
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BEGIN:VEVENT
DTSTART;VALUE=DATE:20270411
DTEND;VALUE=DATE:20270412
DTSTAMP:20260905T210307Z
CREATED:20260905T210307Z
LAST-MODIFIED:20260905T210307Z
UID:3383-1807401600-1807487999@www.historichideaways.com
SUMMARY:10\,000 Maniacs
DESCRIPTION:Sunday\, April 11\, 2027\nKey West Theater\, 512 Eaton Street \n10\,000 Maniacs play the Key West Theater. The band formed in Jamestown\, New York in 1981 and has sold more than 10 million records\, moving from the indie circuit to a central place in the alternative rock of the late 80s and early 90s. \nThe 1987 album In My Tribe was the breakthrough — it stayed on the charts for 77 weeks and produced “Like the Weather” and “What’s the Matter Here?” The platinum albums Blind Man’s Zoo and Our Time in Eden followed\, with “Trouble Me\,” “These Are Days\,” and “Candy Everybody Wants.” Their MTV Unplugged set\, which included their version of “Because the Night\,” sold over four million copies. \nMary Ramsey leads the band today on vocals and viola\, alongside founding members Jerome Augustyniak on drums\, John Lombardo on guitar\, Dennis Drew on keyboards\, and Steven Gustafson on bass\, with Ben Medina on guitar. The band marked its 45th anniversary in 2026 with the Candy Everybody Wants box set covering their Elektra years\, and their first album of new material in over a decade. \nSchedule subject to change. Information courtesy of Key West Theater — visit thekeywesttheater.com for tickets and complete details.
URL:https://www.historichideaways.com/event/10000-maniacs/
LOCATION:Key West Theater\, 512 Eaton Street\, Key West\, FL\, 33040
CATEGORIES:Concerts
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