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
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
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
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
Key of Bones: Curse of the Ghost Pirate – Key West Red Carpet Premiere Fri, 02 Oct at 06:30 pm Tennessee Williams Theatre ENTERTAINMENT
Bahama Village Goombay Festival - A Family Friendly Event Fri, 16 Oct at 12:00 pm Petronia St, Key West, FL 33040, United States FESTIVALS
Nine One Five's Fantasy Fest Parade Viewing Party Sat, 24 Oct at 06:00 pm Nine One Five USD 59 FITNESS
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
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
Sunset Moonrise Sail Sat, 26 Sep at 06:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040
Golden Hour - Sunset Experience by Electroniconch Mon, 19 Oct at 04:00 pm Galleon Marina USD 71 TO 117 FESTIVALS
Buccaneer Booty's been Burgled from Key West Outdoor Exploration Game Thu, 01 Oct at 12:00 am Key West Aquarium USD 13 TRIPS-ADVENTURES
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
That Arena Rock Show Sun, 18 Oct at 07:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 SPORTS
Key West Powerboat Races 2026 - VIP Tent - SUNDAY Sun, 08 Nov at 09:00 am Sunset Pier USD 525 FITNESS
Southernmost Scavenger Hunt's 7th Annual Fantasy Fest Bar Crawl Thu, 22 Oct at 02:00 pm Conch Republic Seafood Company FESTIVALS
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
Dante's Annual Halos & Horns Pool Party Thu, 22 Oct at 12:00 pm Dante's Pool Bar & Restaurant PARTIES
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
Key West Powerboat Races 2026 - General Admission - Fri Fri, 06 Nov at 09:00 am Sunset Pier USD 75 FITNESS
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
Mangoes Drag Brunch Royale Halloween Edition Sun, 01 Nov at 11:30 am Mangoes Restaurant USD 55 TO 66 FITNESS
Full Moon Party At Simonton Beach Reggae Vibes Sat, 26 Sep at 07:00 pm Lagerheads Beach Bar & Watersports USD 30 FITNESS
Key West Powerboat Races 2026 - General Admission - Sun Sun, 08 Nov at 09:00 am Sunset Pier USD 75 FITNESS
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
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
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
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
Mike Stack and Friends on the BIG stage at the Sunset Pier Sun, 11 Oct at 05:30 pm The Sunset Pier at Ocean Key Resort
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 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
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
Royal Aqua Idol Week 3: Country Night! Tue, 22 Sep at 06:00 pm Veterans of Foreign Wars Walter R. Mickens Post 6021 and William Weech American Legion Post 168 MUSIC
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
Candlelight: The Best of Hans Zimmer Fri, 13 Nov at 08:30 pm Key West Theater USD 40 TO 76 CANDLELIGHT-CONCERTS
Swayzees Music Icons Pool Party at Shores Pool Wed, 21 Oct at 02:00 pm Southernmost Beach Resort PARTIES
29th Annual Key West Half Marathon & Runfest Fri, 15 Jan at 04:00 pm Key West Historic Seaport MARATHONS
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
Custom House Holiday Concert & Bazaar Fri, 11 Dec at 05:00 pm Key West Art & Historical Society MUSIC
GLAMOROUS DEAD & UNDEAD POPSTARS PARTY - at Viva's Thu, 22 Oct at 06:00 pm Viva Argentinian Steakhouse USD 19 TO 111 FITNESS
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC