Sunset Celebration at Mallory Square
Sunset Celebration at Mallory Square
January 1 - December 31, 2023

Key West's world-famous Sunset Celebration takes place every evening at Mallory Square close to the foot of Duval Street. Featuring both renowned local and international artists and entertainers, the ...

Waterfront Playhouse: Little Shop of Horrors
Waterfront Playhouse: Little Shop of Horrors
November 29 - December 16, 2023

The deviously delicious Broadway and Hollywood sci-fi smash musical Little Shop of Horrors comes to Waterfront Playhouse for a three-week run. Tickets range from $40 to $75. Showtimes at 8 p.m. along...

Conch Tour Train's Holiday Sights & Festive Nights Tours
Conch Tour Train's Holiday Sights & Festive Nights Tours
December 8 - December 23, 2023

Lively Conch Tour Train tours depart from Key West High School, 2100 Flagler Ave., at 6:30, 7, 7:30, 8 and 8:30 p.m. on evenings from Dec. 8 to 12 and 15 to 23. Included are holiday lights glasses as ...

Old Town Trolley's Holiday Sights & Festive Nights Tours
Old Town Trolley's Holiday Sights & Festive Nights Tours
December 8 - December 23, 2023

The popular green and orange trolleys, festively adorned with holiday lights, showcase Key West's best-decorated neighborhoods, buildings and homes on fun-filled 60-minute excursions. Tours depart ea...

Key West Triathlon
Key West Triathlon
December 10, 2023 7:30 AM

Key West Triathlon Finds a New Home The renowned Key West Triathlon, a major event in the global sports calendar, will be moving to a new location for the upcoming two years. The shift is attributed ...

Key West Artisan Market: Merry Marketplace on the Beach
Key West Artisan Market: Merry Marketplace on the Beach
December 10, 2023 10:00 AM

Shop for holiday treasures from local artisans while enjoying live music, tasty treats, fun drinks, activities for the kids – including a ‘snowman’ building contest and even a visit ...

Lighting of The Menorah
Lighting of The Menorah
December 10, 2023 5:00 PM

Please join us for this joyous tradition - Lighting of the Minorah at Bayview Park

Kids Come First in the Florida Keys - Toy Drive
Kids Come First in the Florida Keys - Toy Drive
December 12, 2023 8:00 AM

Our mission is to provide clothing, personal, and school supplies to every child experiencing financial adversity in Monroe County.  Here at Kids Come First in the Florida Keys, we kno...

Fringe Theater: The Best Christmas Pageant Ever
Fringe Theater: The Best Christmas Pageant Ever
December 12 - December 16, 2023

Mischief and mayhem ensue at the annual Christmas pageant when the town's young hoodlums enact a coup and unexpectedly teach the town the true meaning of Christmas. An endearing family show with perf...

Farm to Table Wine Paired Dinner at the Green Pineapple
Farm to Table Wine Paired Dinner at the Green Pineapple
December 13, 2023 7:30 PM

Wednesday, December 13, 2023 | 7:30pm Farm-to-Table Dinner: Bona Furtuna Sicilian Dinner and Heritage Olive Oil Tasting - Land of Sun and Sea featuring the unique wines of Donna Fugata Winery (four co...

Scott Kirby w. Caffeine Carl
Scott Kirby w. Caffeine Carl
December 14, 2023 7:00 PM

Singer, songwriter, guitarist, storyteller, traveler and road warrior are all words that aptly describe Scott Kirby. Kirby started writing songs after some inspirational late-night words from legendar...

Key West Waterfront Winter Wonderland
Key West Waterfront Winter Wonderland
December 15 - December 30, 2023

The Coffee Butler Amphitheater at Truman Waterfront Park transitions into the Key West Waterfront Winter Wonderland for an all ages, family friendly holiday experience Dec. 15 through 30 including stu...