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. 

Old Town Trolley: Holiday Nights Tours

Dec 9 2024 - 7:45pm to Dec 23 2024 - 7:45pm
December 09 - 23, 2024 Key West Old Town Trolley: Holiday Nights Tours Website Take the trolley for a tour of the Key West residential neighborhoods known for going all-out with holiday home decorations. Make this your new holiday tradition with friends and family. Narrated...Read more
Holiday Events
noche buena

Noche Buena

Dec 24 2024 - 6:00pm
December 24 Key West Old Island Restoration Foundation: Noche Buena Website This Christmas Eve event is a celebration of Key West Cuban heritage. Enjoy a traditional succulent roast pig dinner loaded with sides and topped off with El Mocho's homemade flan. $50 adults, $15 age...Read more
Key West Events
key west waterfront winter wonderland

KEY WEST WATERFRONT WINTER WONDERLAND

Dec 13 2024 - 9:00am to Dec 28 2024 - 8:00pm
December 13 - 28, 2024 Key West Waterfront Winter Wonderland Website Make your Key West holiday experience even more magical at Waterfront Winter Wonderland at Truman Waterfront Park. Coffee Butler Amphitheater transforms into an amazing winter wonderland, with an ice-skating, rides, games, music, holiday lights,...Read more
Upcoming Events
red shoe drop

Red Shoe Drop

Dec 31 2024 - 9:00pm
December 31 Key West New Year's Eve Red Shoe Drop Website Witness Key West's iconic Red Shoe Drop at the Bourbon Street Pub, 724 Duval St. Free to watch from Duval Street; VIP options are to be available for balcony seating. Live entertainment in the...Read more
Upcoming Events
schooners wharf bar new years eve

SCHOONER WHARF BAR: NEW YEAR'S EVE PIRATE WENCH DROP

Dec 31 2024 - 11:00pm
December 31 Key West Schooner Wharf Bar: New Year's Eve Lowering of the Pirate Wench Website Celebrate the New Year in true Schooner Wharf Bar style with the annual Lowering of the pirate wench down the mast of the Schooner America 2.0 at midnight. Enjoy...Read more
Upcoming Events
gatsby flight drop

GREAT GATSBY NEW YEAR'S EVE WITH "PLANE DROP"

Dec 31 2024 - 11:15pm
December 31 Key West New Year's Eve Gatsby Gala at First Flight Island Restaurant & Brewery Website Dress to impress in your Gatsby-era best for First Flight Island Restaurant & Brewery's New Year's Eve gala. Enjoy live music, DJ tunes and the Plane Drop at...Read more
Upcoming Events
conch shell drop

SLOPPY JOE'S BAR: DROPPING OF THE CONCH SHELL

Dec 31 2024 - 11:15pm
December 31 Key West New Year's Eve Conch Shell Drop at Sloppy Joe's Website The arrival of 2025 is to be heralded on Key West's Duval Street with the "drop" of a gigantic manmade conch shell, the symbol of the Florida Keys, to the flat...Read more
Upcoming Events
key west half marathon

Key West Half Marathon & Runfest Weekend

Jan 16 2025 - 7:00am to Jan 20 2025 - 5:00pm
The Annual Key West Half Marathon & 5k is a "bucket list" race.Read more
Races
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
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