Stop by the Chamber of Commerce and snap a selfie with the Fantasy Fest King & Queen Sculpture, then pick up official Fantasy Fest swag. Tag #Keywestchamber and #fantasyfest for a chance to win prizes.

The longest-running drag show in Key West. Valid photo ID required, guests must be 21+. Reservations strongly suggested; no shows Oct 24 & 25. Doors at 8PM.

Femme Fatale Body Art’s all-female team offers body art from small pieces to full-body work, with waterproof/sweat-proof options, plus music, food, and sunset views. Book directly by texting team lead Amanda at 850-596-4065.

A Halloween decorating contest open to all Key West and Stock Island businesses and residents. $1,000 grand prize for Best Spooktacular Showstopper, plus awards for Creepiest Concept, Bloodiest Horror Scene, Best Fantasy Fest Theme Integration, and the Great Pumpkin Award. Entries appear on the official Fantasy Fest app map.

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

Intimate poolside bar with a boutique wine list, mixologist-crafted cocktails, and house-made infusions with fresh-squeezed juices.

Key West’s original medical spa offers mobile hydration IV service. Fantasy Fest special: mobile service fee waived for groups of 5+, with an additional 10% off for groups of 10+.

Nightly karaoke throughout Fantasy Fest week at the Karaoke Lounge, hosted by Stars Karaoke Club and DJ Rico.

Snap a selfie with the giant Fantasy Fest letters at Conch Republic Seafood Company. Happy hour daily 4–7PM in the bar & patio.

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

Morning-after recovery all week long with Deep Eddy Vodka cocktails, Bloody Marys, Dulce Vida frozen margaritas, live entertainment, and giveaways.

A street party in the historic Bahama Village neighborhood with island arts, crafts, food, and nonstop music ranging from reggae to soca.

Barbie/Ken pink costume party benefiting Womankind Key West, with music from DJ Maya and DJ Top Jimmy, a costume contest, photo booth, and pink drink & food specials.

Florida Keys SPCA event crowning the King and Queen of Fantasy Fest after a 6-week fundraising campaign, with a tribute to King Christopher Elwell. Ticketed packages include reserved seating and a 3-course dinner; general admission lawn seating is free. Contact [email protected] for info.

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

Continues from Friday — island arts, crafts, food, and live music at the corner of Petronia and Emma Street.

A local-history photo op referencing former Key West Fire Chief Joseph “Bum” Farto, who disappeared in 1976. Snap a photo and receive a rum shot; donations appreciated.

An official Fantasy Fest undersea-themed pool party at the new Blue Flamingo Resort.

Lantern walk through the hammock, fire-pit dancing “witches,” a hayride, games, a Halloween movie screening, and concessions including popcorn, cider, corn dogs, and roasted corn.

A high-energy tribute concert to classic ’70s and ’80s rock at Sunset Pier.

Fantasy Fest edition of the Artisan Market with fine crafts and art from Florida Keys makers, official Fantasy Fest merch, international food trucks, and live music.

A poolside party with a mythical/serpent theme — DJ, food, and drinks, with jewel-tone and metallic dress encouraged.

Repeat performance of the classic rock tribute show at Sunset Pier.

A rubber-duck-themed pool party with beverage samples, swag, and a chance to win a $200 gift card plus other giveaways from The Tazzle.

Margaritas and a pop-up shop featuring 30 women artists at this all-female gallery.

A “Three’s Company”-themed party with sunset views, music, trivia, games, and specialty drinks. Not ticketed, but donations go entirely to a local charity. Info: 850-596-4065.

Key West’s own Beatle Band performs three sets, with an optional ’60s dress-up theme for the crowd.

“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.

Regency-era masquerade ball and multi-course wine dinner with live music. Masks required; reserve seats at Keystix.com.

$7 martinis all night, plus live music and food.

A dark-fairytale-themed women-only evening with cocktails, a costume contest, VIP lounge access, mask-making, and a photo booth.

Key West’s original Fantasy Fest kink party, in its 28th year, with interactive BDSM stations and fetish rooms. Kinky costume required for entry; cash only. Tickets sold Oct 17–20.

Themed costume party at Sloppy Joe’s with live entertainment throughout the day and night.

Private underwear party with free clothes check.

Patriotic-themed pool party with food and drink specials.

Rum tasting and cocktail-making class featuring Captain Morgan White and Spiced, with two cocktails made and a swag bag included.

Storybook-character costume pool party with two pools, live entertainment, food/drink specials, a costume contest, and hourly vacation raffles.

Meet the winning 2026 poster designer, get posters/shirts/swag, and sample wine courtesy of Bogle Wines.

A walking parade pre-party with a drink stop, feeding into the main Tutu Tuesday event; parade pass includes entry to the Tutu Party.

Six-round Halloween-themed trivia night; costumed players get bonus points. This one is already sold out per the listing.

15th annual dance-party crawl across four venues (First Flight Brewery, Hanks Hair of the Dog Saloon, The Alamo, and General Horseplay as the hub) with 10+ DJs on one wristband. VIP adds treetop lounge access, limited to first 150.

Live Taylor Swift tribute concert performed by local artist Meghan Barter.

Salsa dance instruction while wearing tutus, sponsored by Dulce Vida Organic Tequila, with margarita and sangria specials.

Charity event benefiting the Florida Keys SPCA with unlimited drinks across the Rick’s complex and an animal-costume contest with a $500 grand prize. Contact Jennifer at 305-294-4857 ext. 5.

Plaid-costume party with music and drinks at Capt. Tony’s.

Sleepwear-costume contest themed to “Bedtime Stories & Magical Monsters.” Prizes: $500 / $250 / $100 Sloppy Joe’s gift cards; band “Nightbreakers” plays after the contest.

Pajama or swimwear pool party with live music from Les Greene and the Swayzees, sponsored by Empress Gin.

Clothing-optional pool party at Island House resort; no costumes needed. Admission includes locker, towels, and extended resort access. Photo ID required.

Underwater-monster costume contest. 1st place $1,000, 2nd place a PlayStation 5, plus hotel stays and sunset cruises as additional prizes. Entry includes a drink and appetizer.

Guitar Shred-Off competition ($1,000 cash prize), a live-band set from 9–10PM, then a Costume & Air Guitar Contest at 10PM ($300/$200/$100 prizes). Partial proceeds support a local musician’s medical bills.

“Bedtime Stories & Magical Monsters”-themed evening event with lounges, cocktails, live entertainment, and immersive décor. Pajama-chic to fully costumed attire encouraged.

Pet costume contest with four categories (Junior, Pet/Owner Lookalike, Most Exotic, Best Theme Adaptation) plus Best in Show. Proceeds benefit the Monroe County Sheriff’s Office Animal Farm. Bring a blanket or lawn chair.

’70s disco-themed dance party with local DJs Scott Gerke and Chris Cohen.

1960s Woodstock-themed sit-in with live music from “That Hippie Band,” costume prizes for sexiest hippie chick and grooviest dude (judged 8:30PM).

14th annual UV blacklight glow party with multiple DJs and a Funktion-One sound system. No glow, no entry — come dressed or painted to glow under blacklight. Door price increases night-of (cash only).

Private fetish party with fetish attire encouraged and free clothes check.

Keys-wide open house event; visiting homes enters guests for VIP tickets to a Fantasy Fest Parade viewing party (bonus entry for 3+ open houses visited). Note: source text lists this under “Thursday, October 23rd” — confirm actual date.

Team bar crawl (teams up to 6, 21+) sponsored by Dulce Vida Organic Tequila. Includes a free drink, swag, souvenir cup, and scavenger hunt map. Awards announced 5PM. Note: source text references “October 26th” — this event also recurs on Oct 24; confirm the correct date.

Second round of the pajama/swimwear pool party with live music, sponsored by Dulce Vida Organic Tequila.

Angel/devil-themed pool party with cash prizes, free body painting, live music, and a stage in the center of the pool; pole dancing starts 4:30PM.

Live sets from funk band Funk You, blending modern and vintage dance grooves.

Rooftop pool-deck lounge party with classic cocktails and DJ sets.

The Key West Business Guild’s flagship LGBTQ+ event, judged headdress competition with a $5,000 top prize, emceed by Randy Roberts. Sells out most years — book early via keystix.com or gaykeywestfl.com/headdress-ball. Note: source text says “Thursday, October 23, 2025” — confirm current-year date.

Breast cancer awareness costume/charisma contest with a $500 first prize plus crown and sash, live music from 9PM.

Western/monster costume party with local DJs Scott Gerke and Chris Cohen and late-night food.

Pink-costume party with live entertainment and a costume contest ($500/$250/$100 bar tabs). Note: source text says “Thursday 10/23” — confirm date.

Long-running toga-costume contest, individual or groups of 2–4. Prizes $500/$250/$100 Sloppy Joe’s gift cards; “Nightbreakers” plays after.

Poolside foam party with two dance floors, blacklight room, and exotic dancers. Full access to the pool area with limited free towels and clothes check. Tickets via New Orleans House or Keystix.com.

’80s-themed party with a dedicated cover band taking the stage at 10PM.

Duval Street’s signature mile-long street fair: arts, crafts, and food on Friday, with Saturday shifting focus to food served late into the night.

Poolside dance party / street fair T-Dance with live DJs, drag queens, and games.

Oceanfront infinity-pool party with DJ Hazard and drink specials; bunny ears required for topless sunbathing per venue policy.

Cuban music and dancing street party hosted by the San Carlos Institute, with a mojito bar.

A locals-focused costume parade tradition through Old Town into the Street Fair, with a red-carpet block party, 360-selfie station, and complimentary drinks along the route.

Pirate-themed party with nautical music and a costume contest paying $500/$300/$200.

Surfer-costume party with live music and drink specials.

Body-painting/living-art competition for solo, male, female, or group entries, competing for $2,000 in cash and prizes ($1,000 for Best Overall). Registration via Sunset Pier, 305-295-7047.

Horror-themed drag show from Beatrix Dixie and Jonathan Barrett featuring the Aquanettes. Reservations recommended — tends to sell out. Note: source text says “Friday October 24th” — confirm date.

Couples-exclusive event with a performance from latex entertainer RubberDoll. Pre-registration required; no re-entry once you leave. Repeats Saturday.

Adults-only late-night event at Island House resort. Admission includes first drink, locker, towels, and extended resort access. Photo ID required.

Late-night dance party at the Birdcage Cabaret hosted by Holly Dae, featuring an international DJ.

Ladder-format charity tennis tournament benefiting Keys to Be the Change mentoring programs; includes breakfast, drinks, awards, and lunch. Registration limited to 20 — contact 541-974-4398 or [email protected]. Note: source text says “Saturday, October 25th” — confirm date.

Saturday’s Street Fair shifts focus to food, running late into the night alongside the parade.

Cuban music, dancing, and a mojito bar hosted by the San Carlos Institute.

Parade-day pool party with live DJ and pool games.

Team bar crawl (teams up to 6, 21+) sponsored by Dulce Vida Organic Tequila — same event as listed under Thursday Oct 22; confirm which date is correct before publishing.

Grand-balcony parade viewing with open bar and catered buffet, private entrance and restrooms. Tickets from 305-293-9800 or keystix.com.

Dinner buffet and 3-hour open bar with a choice of sidewalk chair, indoor table, or porch-chair seating for the parade.

Elevated patio parade-viewing with drink specials, a special dinner menu, and live piano from Dave Bootle after the parade.

Reserved-seating parade viewing with hors d’oeuvres, desserts, and two complimentary drinks at Eleanor’s Elixirs Martini Bar. Pajama-themed costumes encouraged; sells out most years.

Outdoor tiki bar and air-conditioned indoor viewing, live music and DJ, plus a live 8-piece Argentine band after the parade.

The main event — floats, costumes, and dance groups down Duval Street in front of a crowd historically numbering in the tens of thousands.

Street-side parade viewing emceed by WEOW’s Rude Girl.

Whimsical mythical-creatures-themed drag show, second half of the two-night Slay Queen event. Reservations recommended.

Second night of the couples-only latex/fetish-themed event with RubberDoll.

Ocean/mermaid-themed party with Jeff Clark’s All Star Band; partial proceeds support Sea Basecamp.

Charity pickleball tournament for Keys to Be the Change, including breakfast, a hat/visor, awards, and lunch. Limited to 40 registrants — 541-974-4398 or [email protected]. Note: source text says “Sunday, October 26th” — confirm date.

Family-friendly festival with food, rides, games, arts and crafts, and a kids’ costume contest.

Clothing-optional pool party with a Sunday raffle. Admission includes locker and towels. Photo ID required.

Recovery-day pool party with food/drink specials and a live DJ. Note: source text says “Sunday, 10/26” — confirm date.

Traditionally the last official event of Fantasy Fest week, with music from DJ Rude Girl.

Sponsored by Dirty Monkey Banana Peanut Butter Whiskey — live reggae music, drink specials, and two pools.

Post-Fantasy-Fest, pre-Halloween golf cart tour of decorated houses and businesses entered in the Facade Contest. Costumes and a golf cart decor contest encouraged; use code FANTASY for 15% off Fury golf cart rentals. Designate a sober driver.