Key West Festivals Events

Freedom Flotilla Festival

Key West, Floirda 19 Dec 2025

31st Annual Taste of Key West

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

Freedom Flotilla Festival

Key West 19 Dec 2025

Florida Keys Seafood Festival

Truman Waterfront Park 14 Feb 2026

Q West: Comedy Escape 2026

Key West Theater 10 Apr 2026

December Duo Holiday Concert: Irie Monte and Crispin Campbell

533 Eaton St, Key West, FL, United States, Florida 33040 13 Dec 2025

Gabriel Rutledge Live in Key West

Key West Theater 15 Feb 2026

Cupid's Chase 5K Key West

Clarence S.Higgs Memorial Beach 14 Feb 2026

61th Annual Key West Art & Craft Festival

Truman Waterfront Park 21 Feb 2026

Changes In Latitude at Key West Theater

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

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

Key West Theatre 14 Feb 2026

Mile 0 Fest - (Saturday)

Coffee Butler Amphitheater 31 Jan 2026

Phil Collins Experience at Key West Theater

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

29th Annual Key West Paddle Classic

Higgs Beach in Key West 9 May 2026

Mile 0 Fest Key West - 3 Day Pass (Thursday-Saturday)

Truman Waterfront Amphitheater 28 Jan 2026

Mile 0 Fest - (Friday)

Coffee Butler Amphitheater 30 Jan 2026

Mile 0 Fest Key West - 5 Day Pass

Truman Waterfront Amphitheater 26 Jan 2026

Mile 0 Fest Key West - Tuesday

Truman Waterfront Amphitheater 26 Jan 2026

Parking Mile 0 Fest - (Friday)

Coffee Butler Amphitheater 30 Jan 2026

Mile 0 Fest Key West - 3 Day Pass (Tuesday-Thursday)

Truman Waterfront Amphitheater 27 Jan 2026

Mile 0 Fest Key West: Randy Rogers Band Kaitlin Butts & Tanner Usrey - Thursday

Truman Waterfront Amphitheater 28 Jan 2026

Mile 0 Fest Key West: Paul Cauthen Cody Canada and The Departed & Them Dirty Roses - Friday

Truman Waterfront Amphitheater 29 Jan 2026

Mile 0 Fest Key West: Stephen Wilson Jr. American Aquarium & Taylor Hunnicut - Wednesday

Truman Waterfront Amphitheater 27 Jan 2026

Mile 0 Fest - (Thursday)

Coffee Butler Amphitheater 29 Jan 2026

Parking Mile 0 Fest - (Thursday)

Coffee Butler Amphitheater 29 Jan 2026

Parking Mile 0 Fest - (Saturday)

Coffee Butler Amphitheater 31 Jan 2026

Parking Mile 0 Fest - (Wednedsay)

Coffee Butler Amphitheater 28 Jan 2026

Parking Mile 0 Fest - (Tuesday)

Coffee Butler Amphitheater 27 Jan 2026

Mile 0 Fest - (Tuesday)

Coffee Butler Amphitheater 27 Jan 2026

Mile 0 Fest Key West: Shane Smith and The Saints Casey Donahew & The Band of Heathens - Saturday

Truman Waterfront Amphitheater 30 Jan 2026

Key West 250th Celebration and Time Capsule Opening 2072

Mallory Square Key West 25 Mar 2026

The Massacoustics at Key West Theater

Key West Theater 4 Feb 2026

Mile 0 Fest - (Wednedsay)

Coffee Butler Amphitheater 28 Jan 2026

WOOF Week 2026!

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

Mile 0 Fest - (5 Day Pass) with Stephen Wilson Jr., Randy Rogers Band, Cross Canadian Ragweed

Coffee Butler Amphitheater 27 Jan 2026

Parking Mile 0 Fest - (5 Day Pass) with Stephen Wilson Jr., Randy Rogers Band, Cross Canadian Ragweed

Coffee Butler Amphitheater 27 Jan 2026

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

Ernest Hemingway House 29 Nov 2025