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
Paparazzi Row Block Party Fri, 23 Oct 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
Gold Pool Parties Sun, 20 Sep 1129 Fleming St, Key West, FL, United States, Florida 33040 POOL-PARTIES
Havana Cabana At Key West's Duck, Duck, Booze Pool Party Mon, 19 Oct at 12:00 pm Havana Cabana Key West 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
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
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
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
2026 - Saturday, Oct. 31 - Jerry Diaz's Key West Sunset "Booze Cruise"! Sat, 31 Oct at 04:00 pm Sebago Watersports MUSIC
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
Photo Op Fest Letters All Day Fri, 16 Oct at 10:00 am 631 Greene St, Key West, FL 33040-6624, United States FESTIVALS
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
Key West Lighted Boat Parade Sat, 12 Dec at 08:00 pm 0 Duval Street, Key West, FL, United States, Florida 33040 PARADES
Third Annual Key West Woman's Club Bougie Afternoon Tea Party Sat, 16 Jan at 03:00 pm 319 Duval St, Key West, FL, United States, Florida 33040 ENTERTAINMENT
Last Sunset Sail of 2026! Thu, 31 Dec at 04:15 pm 0 Duval Street, Key West, FL, United States, Florida 33040 DOG
Annual Holiday Ornament Paint Night With Jess Thu, 03 Dec at 05:30 pm 22&Co Key West DRAWING-PAINTING
Valentine's Day Sunset Sail Sun, 14 Feb at 04:45 pm 0 Duval Street, Key West, FL, United States, Florida 33040 DOG