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
Key West OktoBREWfest Sat, 03 Oct at 03:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040
Fantasy Fest Street Fair & Costume Promenade Fri, 23 Oct at 12:00 pm Duval St, Key West, FL 33040, United States FESTIVALS
Bahama Village Goombay Festival - A Family Friendly Event Fri, 16 Oct at 12:00 pm Petronia 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 FESTIVALS
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
Nine One Five's Fantasy Fest Parade Viewing Party Sat, 24 Oct at 06:00 pm Nine One Five USD 59 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
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 PARTIES
Gold Pool Parties Sun, 20 Sep 1129 Fleming St, Key West, FL, United States, Florida 33040 POOL-PARTIES
Lip Sync & Lifeguards - A Fantasy Fest Pool Party Sat, 17 Oct at 12:00 pm Blue Flamingo Resort Key West FREE 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
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
Golden Hour - Sunset Experience by Electroniconch Mon, 19 Oct at 04:00 pm Galleon Marina USD 71 TO 117 FESTIVALS
Key West Powerboat Races 2026 - VIP Tent - SUNDAY Sun, 08 Nov at 09:00 am Sunset Pier USD 525 FITNESS
Key West Powerboat Races 2026 - VIP Tent - FRIDAY Fri, 06 Nov at 09:00 am Sunset Pier USD 525 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
Southernmost Scavenger Hunt's 7th Annual Fantasy Fest Bar Crawl Thu, 22 Oct at 02:00 pm Conch Republic Seafood Company FESTIVALS
Dante's Annual Halos & Horns Pool Party Thu, 22 Oct at 12:00 pm Dante's Pool Bar & Restaurant PARTIES
Halloween Eve Bar Crawl 10/30 - KEY WEST Fri, 30 Oct at 05:00 pm La Concha Key West, Autograph Collection USD 16 TO 19 PARTIES
NINA STYLY X ELECTRONICONCH RECORDS - FASHION THROGHT SOUND Fri, 23 Oct at 10:00 pm Viva Argentinian Steakhouse ART
Halloween Bar Crawl 10/31 - KEY WEST Sat, 31 Oct at 04:00 pm La Concha Key West, Autograph Collection USD 16 TO 19 FITNESS
Pool Party, Cannonball Contest, Tea Dance Sun, 27 Sep at 01:00 pm Southernmost Beach Resort, La Te Da CONTESTS
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
Haunted "Conch Train"! The CREEPY Story of Carl Tanzler! Thu, 08 Oct at 07:00 pm Southernmost Beach Resort NONPROFIT
Sins & Sequins - An Official Fantasy Fest Event Wed, 21 Oct at 07:00 pm Blue Flamingo Resort Key West USD 31 FITNESS
Full Moon Ghost Show Sat, 26 Sep at 07:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040
Tutu Tuesday Pre-Party Bar Crawl Tue, 20 Oct at 04:30 pm 420 Applerouth Ln, Key West, FL 33040-6535, United States PARTIES
Full Moon Party At Simonton Beach Reggae Vibes Sat, 26 Sep at 07:00 pm Lagerheads Beach Bar & Watersports USD 30 FITNESS
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
Key West Murder Mystery 2: Crime on Date Night! Thu, 01 Oct at 12:00 am 502 Whitehead St, Key West USD 15 TRIPS-ADVENTURES
Fantasy Fest Royal Campaign All Candidate Event at The Gardens Hotel! Wed, 14 Oct at 05:00 pm Gardens Hotel FESTIVALS
Barbie's Pink Pool Party For Breast Cancer Awareness At The Marker Fri, 16 Oct at 04:00 pm The Marker Key West Resort NONPROFIT
Floatapalooza Fantasy Fest at The Reach Thu, 22 Oct at 11:00 am 1435 Simonton St, Key West, FL 33040 FESTIVALS
"Rhinestones & Rocky Horror" themed CommuniTEA Dance benefiting Marc Key West Sat, 26 Sep at 04:30 pm Alexander's Guesthouse Key West NONPROFIT
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
GLAMOROUS DEAD & UNDEAD POPSTARS PARTY - at Viva's Thu, 22 Oct at 06:00 pm Viva Argentinian Steakhouse USD 19 TO 111 FITNESS
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
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
Fantasy Fest Body Paint at Margaritaville! Sun, 18 Oct at 11:00 am Margaritaville Restaurant, Key West FESTIVALS
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
Dirty Doctors Naughty Nurses Party Sat, 24 Oct at 09:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 41 TO 75 FITNESS
Krewe de Krazy Life Meet and Greet and Costume Parts Exchange Sun, 18 Oct at 12:00 pm Galleon Tiki Bar MEET-AND-GREET
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
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC
Swayzees Music Icons Pool Party at Shores Pool Wed, 21 Oct at 02:00 pm Southernmost Beach Resort PARTIES
Key West 11th Annual Casino Night by SOS Foundation Fri, 13 Nov at 06:30 pm Casa Marina Key West, Curio Collection by Hilton FITNESS
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
2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise" Fri, 30 Oct at 05:00 pm Sebago Watersports MUSIC
Rockin' it as Cowboys, Cowgirls, and Indians Thu, 22 Oct at 08:00 pm Captain Tony's Saloon Key West FESTIVALS
Copy of Seattle Hidden Gems Experience Tue, 28 Jul at 10:00 am Mallory Square USD 23 TRIPS-ADVENTURES
Mangoes Drag Brunch Royale Christmas Show Sun, 20 Dec at 11:30 am Mangoes Restaurant USD 55 TO 66 FITNESS
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
October's Community Swim Sat, 17 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
STUDIO 69 DISCO PARTY - at Viva's Wed, 21 Oct at 06:00 pm Viva Argentinian Steakhouse USD 11 TO 111 FITNESS
Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys! Sat, 14 Nov at 06:00 pm Key West Aquarium USD 13 FITNESS
Greatest Hits Pool Party at Winslow's Bungalows Tue, 20 Oct at 12:00 pm 725 Truman Ave, Key West, FL 33040-6423, United States PARTIES
Dinner with Entrepreneurs: Small Town, Small Business Edition | Key West Sat, 13 Dec at 07:00 pm Restaurant of the Week USD 29 TO 55 FITNESS
Welcome To The Jungle Party Tue, 20 Oct at 08:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 30 TO 58 FITNESS
Trivia Night Wed, 04 Nov at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 FESTIVALS
A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg, Reese Dailey & Special Guests Sat, 13 Feb at 08:00 pm Key West Theatre ART
An Evening Aglow: A Candlelight Christmas with Marjory Lee Tue, 15 Dec at 08:00 pm Key West Theater MUSIC
Photo Op Fest Letters All Day Fri, 16 Oct at 10:00 am 631 Greene St, Key West, FL 33040-6624, United States FESTIVALS
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band Fri, 01 Jan at 08:00 pm Key West Theater MUSIC
2027 Cupid's Chase 5K Key West Sat, 13 Feb at 09:00 am Higgs Beach Pavilion, 1000 Atlantic Boulevard, Key West, FL US 33040 SPORTS