Key West Events Calendar

From annual festivals to holiday celebrations, the fun never stops in Key West. We're looking forward to these upcoming Key West events. For details on any event or planning a holiday vacation, contact our local team! We're happy to provide nearby vacation rental recommendations and the inside scoop on all things Key West. 

vfw fishing contest

VFW Fishing Tournament

Jun 20 2025 - 7:00am to Jun 22 2025 - 7:00pm
June 20 - 22, 2025 Key West VFW Fishing Tournament Website VFW's annual fishing tournament returns with over $75,000 in cash and prizes. The big change for 2025 will be that all registered boats are able to fish two days, with no separate registration required...Read more
Upcoming Events
key west pride

Key West Pride

Jun 22 2025 - 8:00am to Jun 29 2025 - 5:00pm
June 22 - 29, 2025 Key West KEY WEST PRIDE WEBSITE Celebrate PRIDE on the tropical island of Key West that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with friends, travel with family, or to...Read more
Upcoming Events
4th of july fireworks

Studios of Key West: 4th of July Rooftop Fireworks Viewing

Jul 4 2025 - 7:15pm
July 04 Key West Studios of Key West: 4th of July Rooftop Fireworks Viewing Website Join Studios of Key West for a special Independence Day party on the Hugh's View rooftop! Ticket price includes a free drink, a view of the fireworks on the horizon,...Read more
Upcoming Events
key lime festival

Key Lime Festival

Jul 2 2025 - 7:00am to Jul 5 2025 - 11:00pm
July 02 - 05, 2025 Key West Key Lime Festival Website The Key Lime Festival celebrates the world’s most sensational citrus with a spectacular lineup of festivities taking place across Key West, the island where Key lime pie was conceived. Highlights include a kick-off cookbook...Read more
Upcoming Events
key west marlin tournament

KEY WEST MARLIN TOURNAMENT

Jul 16 2025 - 7:00am to Jul 23 2025 - 9:00pm
July 16 - 23, 2025 Key West Key West Marlin Tournament Website Coinciding with the 45th annual Hemingway Days celebration, anglers ply the waters once fished by novelist Ernest Hemingway, vying for $50,000 in guaranteed cash prizes. The event awards $25,000 to the first-place team...Read more
Upcoming Events

HEMINGWAY DAYS: RUNNING OF THE BULLS

Jul 26 2025 - 1:00pm
July 26 Key West Hemingway Days: Running of the Bulls Website A festival tradition, this wacky event is sponsored by Sloppy Joe’s Bar and features Hemingway Look-Alike Contest winners and entrants dressed in their Pamplona best — and a breed of “bull” found only in...Read more
Upcoming Events

Hemingway Days

Jul 22 2025 - 8:15am to Jul 27 2025 - 8:15pm
July 22 - 27, 2025 Key West Hemingway Days Website Ernest Hemingway look-alikes, writers, anglers, and fans of the late author’s work are to gather in Key West for the annual Hemingway Days celebration. The festival honors the legacy of the American literary giant who...Read more
Upcoming Events
hemingway sunset run

Hemingway 5k Sunset Run & Beach n' Beer Mile

Jul 26 2025 - 12:00pm to Jul 27 2025 - 8:30pm
July 26 - 27, 2025 Key West Hemingway 5k Sunset Run & Beach n' Beer Mile Website Join fellow runners and walkers for the 36th annual Hemingway 5k Sunset Run. This year, final registration for the evening race is at Southernmost Beach Cafe, 1405 Duval...Read more
Upcoming Events
Hemingway Look Alikes

Sloppy Joe's 44th Annual Hemingway Look-Alike Contest

Jul 23 2025 - 8:00am to Jul 27 2025 - 10:00pm
July 23 - 27, 2025 Key West Sloppy Joe's 44th Annual Hemingway Look-Alike Contest Website The look-alike challenge is a highlight of Key West’s July 23-27 Hemingway Days celebration, created to salute the writing talent and adventurous life of the literary master who lived and...Read more
Upcoming Events
tropical heat

Key West Tropical Heat

Aug 13 2025 - 9:00am to Aug 17 2025 - 8:00pm
August 13 - 17, 2025 Key West Key West Tropical Heat Website Enjoy five days of sizzling happenings in the island city whose openness and respect for diversity have made it a world-renowned gay vacation destination. The festival’s events range from all-male theme parties, pool...Read more
Upcoming Events

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