Key West Festivals Events

Golf Cart Facade Viewing Tour Fantasy Fest

3128 N. Roosevelt Blvd., Key West, FL, United States, Florida 33040 29 Oct 2025

Key West Powerboat Races 2025 - Hot Tin Roof Balcony - SUNDAY

Hot Tin Roof Restaurant 9 Nov 2025

31st Annual Taste of Key West

Truman Waterfront, Key West, FL, United States, Florida 33040 23 Mar 2026

DEADFEST KEY WEST - FALL SESSIONS - DEC 5th, 6th & 7th

The Alamo Key West 5 Dec 2025

Wesley House Holiday Village & Bike Ride

Coffee Butler Amphitheater 5 Dec 2025

Q West: Comedy Escape 2026

Key West Theater 10 Apr 2026

Melon Jelly LIVE @ The Alamo, Key West FL 🎶

The Alamo Key West 21 Nov 2025

Shoreline Sessions Reggae Beach Festival

1319 Duval Street, Key West, FL, United States, Florida 33040 1 Nov 2025

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025

61th Annual Key West Art & Craft Festival

Truman Waterfront Park 21 Feb 2026

Freedom Flotilla Festival

Key West 19 Dec 2025

CFK Community Day 2025

5901 College Rd, Key West, FL 33040-4315, United States 1 Nov 2025

Wheeland Brothers

Key West Theater 8 Nov 2025

Cupid's Chase 5K Key West

Clarence S.Higgs Memorial Beach 14 Feb 2026

Florida Keys Seafood Festival

Truman Waterfront Park 14 Feb 2026

FANTASY FEST. STREET FAIR

700 Duval St, Key West, FL 33040-7404, United States 1 Nov 2025

Changes In Latitude at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 3 Mar 2026

The Carole King & James Taylor Story ft. Phoebe Katis & Dan Clews

Key West Theater 25 Nov 2025

A Tribute to the Songs of Pat Dailey in Key West with Ray Fogg and Reese Dailey

Key West Theatre 14 Feb 2026

Phil Collins Experience at Key West Theater

512 Eaton St, Key West, FL, United States, Florida 33040 26 Jan 2026

Key West 250th Celebration and Time Capsule Opening 2072

Mallory Square Key West 25 Mar 2026

2025 - Friday, Oct. 31 - Jerry Diaz's Sunset Cruise in Key West!

Sebago Key West 31 Oct 2025

Crooks Second Line Parade

111 Olivia St (temporary during construction), Key West, FL 15 Feb 2026

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026

Southernmost Turkey Trot 5K

The Southernmost Point Buoy 27 Nov 2025

Fantasy Fest

Key West, Florida 26 Oct 2025

WOOF Week 2026!

1129 Fleming St, Key West, FL, United States, Florida 33040 21 Apr 2026

Key West Audio Tour: Hemingway’s Haunts and Island Legends

Ernest Hemingway House 25 Oct 2025