Deep Eddy Vodka 2026 Fantasy Fest Parade Sat, 24 Oct at 07:00 pm Duval St, Key West, FL 33040, United States PARADES
Captain Morgan's Masquerade March Fri, 23 Oct at 05:30 pm 1117 Fleming St, Key West, FL 33040-6909, United States PARTIES
The Fright Crawl | Key West's #1 Halloween Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 07:30 pm TBA USD 8 TO 82 FITNESS
The Fright Crawl | Key West Halloween Day Bar Crawl 2026 | Sat, Oct 31 Sat, 31 Oct at 01:00 pm TBA USD 8 TO 71 FITNESS
Fantasy Fest Street Fair & Costume Promenade Fri, 23 Oct at 12:00 pm Duval St, Key West, FL 33040, United States FESTIVALS
LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West Wed, 21 Oct at 08:00 pm Rick's Bar USD 36 TO 117 FITNESS
2026 Fantasy Fest Parade Viewing Party @ First Flight Sat, 24 Oct at 06:00 pm First Flight Island Restaurant & Brewery USD 177 TO 562 PARADES
Paparazzi Row Block Party Fri, 23 Oct 1129 Fleming St, Key West, FL, United States, Florida 33040 PARTIES
Friday Night Fever Fantasy Fest Party at Hog's Breath *FREE EVENT* Fri, 23 Oct at 07:00 pm 400 Front St, Key West, FL, United States, Florida 33040 FESTIVALS
Nine One Five's Fantasy Fest Parade Viewing Party Sat, 24 Oct at 06:00 pm Nine One Five USD 59 FITNESS
Bahama Village Goombay Festival - A Family Friendly Event Fri, 16 Oct at 12:00 pm Petronia St, Key West, FL 33040, United States FESTIVALS
The Fright Crawl | Key West Halloween Bar Crawl 2026 | Fri, Oct 30 Fri, 30 Oct at 07:30 pm TBA USD 8 TO 71 FITNESS
Lip Sync & Lifeguards - A Fantasy Fest Pool Party Sat, 17 Oct at 12:00 pm Blue Flamingo Resort Key West FREE FITNESS
Golden Hour - Sunset Experience by Electroniconch Mon, 19 Oct at 04:00 pm Galleon Marina USD 82 TO 128 FITNESS
The Fright Crawl | Key West Halloween Bar Crawl 2026 | Thurs, Oct. 29 Thu, 29 Oct at 07:30 pm TBA USD 8 TO 71 FITNESS
Key West Powerboat Races 2026 - VIP Tent - FRIDAY Fri, 06 Nov at 09:00 am Sunset Pier USD 525 FITNESS
Midnight Mass: A Heated GAYthering Fri, 23 Oct at 10:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040 PARTIES
NINA STYLY X ELECTRONICONCH RECORDS - FASHION THROGHT SOUND Fri, 23 Oct at 10:00 pm Viva Argentinian Steakhouse ART
Southernmost Scavenger Hunt's 7th Annual Fantasy Fest Bar Crawl Thu, 22 Oct at 02:00 pm Conch Republic Seafood Company FESTIVALS
Halloween Bar Crawl 10/31 - KEY WEST Sat, 31 Oct at 04:00 pm La Concha Key West, Autograph Collection USD 20 TO 25 FITNESS
Halloween Eve Bar Crawl 10/30 - KEY WEST Fri, 30 Oct at 05:00 pm La Concha Key West, Autograph Collection USD 20 TO 25 FITNESS
VIVA'S GRAND FINALE - FANTASY FEST PARADE VIEWING & DINNER PARTY Sat, 24 Oct at 06:00 pm Viva Argentinian Steakhouse USD 86 TO 168 FITNESS
Sins & Sequins - An Official Fantasy Fest Event Wed, 21 Oct at 07:00 pm Blue Flamingo Resort Key West USD 31 FITNESS
Dante's Annual Halos & Horns Pool Party Thu, 22 Oct at 12:00 pm Dante's Pool Bar & Restaurant PARTIES
Tutu Tuesday Pre-Party Bar Crawl Tue, 20 Oct at 04:30 pm 420 Applerouth Ln, Key West, FL 33040-6535, United States PARTIES
That Arena Rock Show Sun, 18 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 SPORTS
WE LOVE DOLLY! 💖 A Dolly Parton Tribute Party Tue, 20 Oct at 04:00 pm 431 Front St, Key West, FL 33040-6663, United States FESTIVALS
Mangoes Drag Brunch Royale Halloween Edition Sun, 01 Nov at 11:30 am Mangoes Restaurant USD 55 TO 66 BRUNCH
Gold Pool Parties Sun, 20 Sep 1129 Fleming St, Key West, FL, United States, Florida 33040 POOL-PARTIES
ABC ( Anything But Clothes ) Party Wed, 21 Oct at 08:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 30 TO 58 FITNESS
Key West Powerboat Races 2026 - General Admission - Fri Fri, 06 Nov at 09:00 am Sunset Pier USD 75 FITNESS
Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL Fri, 21 Aug Illusions the Drag Queen Show Key West USD 13 TO 914 ENTERTAINMENT
Havana Cabana At Key West's Duck, Duck, Booze Pool Party Mon, 19 Oct at 12:00 pm Havana Cabana Key West FESTIVALS
Floatapalooza Fantasy Fest at The Reach Thu, 22 Oct at 11:00 am 1435 Simonton St, Key West, FL 33040 FESTIVALS
The Gold Party - Fantasy Fest Edition! Wed, 21 Oct at 05:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040 FESTIVALS
Irish Kevin's Annual 80's Party Thu, 22 Oct at 10:00 pm 211 Duval St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
Candlelight: Coldplay vs. Imagine Dragons Fri, 13 Nov at 06:00 pm Key West Theater USD 40 TO 76 ENTERTAINMENT
Key West Powerboat Races 2026 - General Admission - Sun Sun, 08 Nov at 09:00 am Sunset Pier USD 75 SPORTS
Florida Keys Council of the Arts Fantasy Fest Poster Signing Party Tue, 20 Oct at 03:00 pm La Concha Key West FESTIVALS
Mamma Mia’s Margaritaville Pool Party Mon, 19 Oct at 11:00 am 2001 S Roosevelt Blvd, Key West, FL 33040-5243, United States PARTIES
Muscle Men Male Strippers Revue & Male Strip Club Shows Key West FL Fri, 02 Oct Muscle Men Male Strippers Key West USD 13 TO 914 PARTIES
Candlelight: The Best of Hans Zimmer Fri, 13 Nov at 08:30 pm Key West Theater USD 40 TO 91 CANDLELIGHT-CONCERTS
Asylum Circus Haunted House for all ages! Fri, 30 Oct at 05:00 pm 1908 Flagler Ave., Key West, FL GHOST-HUNTS
KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER Sat, 14 Nov at 05:00 pm Half Shell Raw Bar USD 109 TO 215 FITNESS
Tay-Tay Tuesday - Life of a Showgirl Tue, 20 Oct at 06:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 ENTERTAINMENT
FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY Fri, 23 Oct at 06:00 pm Viva Argentinian Steakhouse USD 11 TO 111 ENTERTAINMENT
A Tribute to the Songs of Pete & Wayne with Pete Jarvis, Larry Strickland, Ray Fogg & Special Guests Sat, 14 Nov at 08:00 pm Key West Theatre COMEDY
34rd Annual ABC 10K/5K Run/Walk Sat, 07 Nov at 07:30 am 1000 Atlantic Blvd, Key West, FL 33040-4852, United States SPORTS
Welcome To The Jungle Party Tue, 20 Oct at 08:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 30 TO 58 FITNESS
Pimp And Ho Party Fri, 23 Oct at 08:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 41 TO 75 ENTERTAINMENT
Fantasy Sunsets Vip Yacht Experience Fri, 16 Oct at 06:00 pm The Perry Hotel & Marina Key West USD 227 FOOD-DRINKS
Masquerade Monday Wine Dinner Presented by Bogle Wines Mon, 19 Oct at 06:00 pm A&B Lobster House MUSIC
Swayzees Music Icons Pool Party at Shores Pool Wed, 21 Oct at 02:00 pm Southernmost Beach Resort PARTIES
Full Moon Magic Ghost Stories Mon, 26 Oct at 07:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 GHOST-HUNTS
Les Greene & The Swayzees Musical Icons Pool Party Take 2 At The Marker Resort Thu, 22 Oct at 02:00 pm The Marker Key West Resort PARTIES
“MOULIN ROUGE”: Sing-Along Movie Night In The Courtyard Thu, 22 Oct at 12:00 pm 524 Front St, Key West, FL 33040-6658, United States ENTERTAINMENT
Fantasy Fest Royal Campaign All Candidate Event at The Gardens Hotel! Wed, 14 Oct at 05:00 pm Gardens Hotel FESTIVALS
GLAMOROUS DEAD & UNDEAD POPSTARS PARTY - at Viva's Thu, 22 Oct at 06:00 pm Viva Argentinian Steakhouse USD 19 TO 111 FITNESS
SOMO Short "Cut" DEAD ZONE Block & Watch Party Sun, 18 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 PARTIES
Dirty Doctors Naughty Nurses Party Sat, 24 Oct at 09:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 41 TO 75 FITNESS
Rockin' it as Cowboys, Cowgirls, and Indians Thu, 22 Oct at 08:00 pm Captain Tony's Saloon Key West FESTIVALS
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC
Fantasy Fest Body Paint at Margaritaville! Sun, 18 Oct at 11:00 am Margaritaville Restaurant, Key West FESTIVALS
Scotty Ziegler at Monarch Gallery Thu, 22 Oct at 06:00 pm 910 Duval Street, Key West, FL, United States, Florida 33040 FESTIVALS
Fantasy Fest 26th Annual Living Art Expo Fri, 23 Oct at 08:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 FESTIVALS
Krewe de Krazy Life Meet and Greet and Costume Parts Exchange Sun, 18 Oct at 12:00 pm Galleon Tiki Bar MEET-AND-GREET
Buccaneer Booty's been Burgled from Key West Outdoor Exploration Game Sun, 01 Nov at 12:00 am Key West Aquarium USD 13 TRIPS-ADVENTURES