Deep Eddy Vodka 2026 Fantasy Fest Parade Sat, 24 Oct at 07:00 pm Duval St, Key West, FL 33040, United States 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 FITNESS
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 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
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
Paparazzi Row Block Party Fri, 23 Oct 1129 Fleming St, Key West, FL, United States, Florida 33040 PARTIES
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 | Thurs, Oct. 29 Thu, 29 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
Midnight Mass: A Heated GAYthering Fri, 23 Oct at 10:00 pm 1129 Fleming St, Key West, FL, United States, Florida 33040 PARTIES
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
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
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
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
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 ENTERTAINMENT
Asylum Circus Haunted House for all ages! Fri, 30 Oct at 05:00 pm 1908 Flagler Ave., Key West, FL GHOST-HUNTS
Dirty Doctors Naughty Nurses Party Sat, 24 Oct at 09:00 pm Southernmost Pint Brewpub - Blast Beer Company Brewery USD 41 TO 75 FITNESS
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
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
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
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
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC
Krewe de Krazy Life Meet and Greet and Costume Parts Exchange Sun, 18 Oct at 12:00 pm Galleon Tiki Bar MEET-AND-GREET
Texas Trop Rock: Jerry Diaz, Dan Sullivan, Jonas Lorence Band Sat, 31 Oct at 01:00 pm Key West Theater MUSIC
Key West 11th Annual Casino Night by SOS Foundation Fri, 13 Nov at 06:30 pm Casa Marina Key West, Curio Collection by Hilton USD 18 TO 135 NONPROFIT
2026 - Friday, Oct. 30 - Jerry Diaz's Key West Sunset "Booze Cruise" Fri, 30 Oct at 05:00 pm Sebago Watersports MUSIC
Custom House Holiday Concert & Bazaar Fri, 11 Dec at 05:00 pm Key West Art & Historical Society MUSIC
Key West Murder Mystery 2: Crime on Date Night! Sun, 01 Nov at 12:00 am 502 Whitehead St, Key West USD 15 TRIPS-ADVENTURES
Fantasy Fest Les Greene & the Swazees The Marker Key West Harbor Resort on October 22 Thu, 22 Oct at 02:00 pm The Marker Key West Harbor Resort FREE FESTIVALS
October's Community Swim Sat, 17 Oct at 06:00 pm 1319 Duval Street, Key West, FL, United States, Florida 33040 MUSIC
IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour Wed, 11 Nov at 07:30 pm Congregation B'nai Zion USD 18 TO 29 MUSIC
Candlelight: Vivaldi's Four Seasons Fri, 11 Dec at 06:00 pm Key West Theater USD 40 TO 88 ENTERTAINMENT
32nd Annual Hog's Breath Saloon Hog Trot 5K Sat, 28 Nov at 08:00 am 400 Front St, Key West, FL, United States, Florida 33040 SPORTS
Candlelight: Tribute to Fleetwood Mac Fri, 11 Dec at 08:30 pm Key West Theater USD 40 TO 76 ENTERTAINMENT
Copy of Seattle Hidden Gems Experience Tue, 28 Jul at 10:00 am Mallory Square USD 23 TRIPS-ADVENTURES
The Broken Hearts: A Tribute to Tom Petty & The Heartbreakers Sat, 12 Dec at 08:00 pm Key West Theater MUSIC
December Duo Holiday Concert: Irie Monte and Crispin Campbell Sat, 12 Dec at 06:00 pm 533 Eaton St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
An Evening Aglow: A Candlelight Christmas with Marjory Lee Tue, 15 Dec at 08:00 pm Key West Theater MUSIC
The Restless Natives: Macon, Georgia's tribute to The Allman Brothers Band Fri, 01 Jan at 08:00 pm Key West Theater MUSIC
Fantasy Fest Barbie Pink Pool Party at The Marker Key West Harbor Resort on October 16 Fri, 16 Oct at 04:00 pm The Marker Key West Harbor Resort PARTIES