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. 

latin festival

Latin Fest

Mar 22 2025 - 10:00am to Mar 23 2025 - 10:00pm
March 22 - 23, 2025 Key West Latin Festival Key West Website Enjoy a lively combination of food, music and culture during the family-friendly Latin Festival at Bayview Park, 1320 Truman Ave. Restaurants participating include El Siboney, El Mocho, El Habanero, Sandy's Cafe and more.Read more
Upcoming Events
tennessee williams

TENNESSEE WILLIAMS FESTIVAL

Mar 2 2025 - 10:00am to Mar 26 2025 - 8:00pm
March 02 - 26, 2025 Key West TENNESSEE WILLIAMS FESTIVAL WEBSITE In celebration of Tennessee Williams, the Pulitzer-prize winning literary icon that moved to Key West in 1949 and remained a resident for 34 years, the Key West Art & Historical Society hosts an annual...Read more
Upcoming Events
schooner bar wreckers cup race

Schooner Wharf Bar: Wrecker's Cup Race

Mar 30 2025 - 1:00pm
March 30 Key West Schooner Wharf Bar: Wrecker's Cup Race Website Set your sails for the 40th annual Wrecker's Cup Race series. Sailing vessels of all sizes are welcome to join the regatta. A captain's meeting is to be held Sat. night, March 29, with...Read more
Upcoming Events
spanish fly shark tournament

Spanish Fly Shark Tournament

Apr 3 2025 - 7:00am to Apr 5 2025 - 5:00pm
April 03 - 05, 2025 Key West Spanish Fly Shark Tournament Website The 2nd annual Spanish Fly Shark Tournament comes to Key West Yacht Club, 2315 N. Roosevelt Blvd. with another exciting event dedicated to gathering data on the bull shark population in the Keys...Read more
Upcoming Events
mote marine

Mote Marine's Ocean Fest

Apr 12 2025 - 10:00am
April 12 Key West Truman Waterfront Park: Mote Marine's Ocean Fest Website Underwater and outdoor enthusiasts, ecotravelers and families are encouraged to celebrate the marine environment at Mote’s Ocean Fest: A Community Celebration. Proceeds and donations from the festival support Mote Marine Laboratory’s coral reef...Read more
Upcoming Events
key west earth day

Earth Day 5K Run/Walk

Apr 19 2025 - 7:00am
April 19 Key West Earth Day 5k Run/Walk Website The Key West Southernmost Runners' 26th annual Earth Day 5k Run/Walk takes place Saturday at Truman Waterfront Park at the end of Southard St. The start and finish line is near the U.S .Coast Guard Cutter...Read more
Upcoming Events
key west songwriters festival

Key West Songwriters Festival

Apr 30 2025 - 7:00am to May 4 2025 - 11:30pm
SAVE THE DATE!! 29th Annual Key West Songwriters Festival April 30 - May 4, 2025Read more
Upcoming Events
swim around key west

College of the Florida Keys Swim Around Key West

Jun 14 2025 - 7:00am
June 14 Key West College of the Florida Keys Swim Around Key West Email Website Embark on an adventurous competitive swim - a 12.5 loop around the island. The pristine waters around Key West give swimmers great views of both the land and underwater life...Read more
Upcoming Events

Key West Gator Club Dolphin Derby

Jun 13 2025 - 7:00am to Jun 15 2025 - 7:00pm
June 13 - 15, 2025 Key West Key West Gator Club Dolphin Derby Website Anglers targeting dolphin fish can compete for $15 thousand in guaranteed cash prizes during the Key West Gator Club Dolphin Derby June 13 through 15. Tournament location to be announced. The...Read more
Upcoming Events
sunset celebration

Summer Solstice Celebration

Jun 1 2025 - 7:00pm to Jun 20 2025 - 9:15pm
June 01 - 20, 2025 Key West Summer Solstice Celebration at Mallory Square: June 1-20 Website Every evening in Key West, locals and visitors gather at the waterfront Mallory Square for the world-famous Sunset Celebration, to enjoy the unique gathering of skilled artisans, exciting performers,...Read more
Upcoming Events

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