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. 

holiday village and belighted bike ride

Holiday Village and Belighted Bike Ride

Dec 1 2023 - 4:00pm
The Wesley House Family Services’ Holiday Village & BeLighted Bike Ride from 4 to 8 Truman Waterfront Park's Coffee Butler Amphitheater, 21 Quay Rd., is a fun-filled, festive evening for all ages and a great way to kick off the Keys' Holiday season. The...Read more
key west holiday parade

Key West Holiday Parade

Dec 2 2023 - 7:00pm
Charming holiday spirit abounds in this annual parade in the southernmost city in the continental U.S. Local flavor prevails with marching bands, school groups, motorized and non-motorized floats and lively community participation. The parade kicks off at 7 p.m. at Truman Avenue and White Street...Read more
key west lighted boat parade

Schooner Wharf Bar Lighted Boat Parade

Dec 9 2023 - 8:00pm
Deck the hulls, it's time for the annual Schooner Wharf Lighted Boat Parade along Key West Bight and Harbor. The glittering parade of illuminated watercraft begins at 8 p.m. There are multiple viewing spots from bars and restaurants and from spots all along the Harbor...Read more
key west waterfront winter wonderland


Dec 15 2023 - 9:00am to Dec 30 2023 - 8:00pm
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 stunning light displays, an ice skating rink, games, rides, attractions, music and more. The amphitheater’s vendor...Read more
new year's eve wench drop


Dec 31 2023 - 11:00pm
Schooner Wharf Bar invites you to join the party to witness the annual tradition of the Lowering of Pirate Wench Evalena, who will once again descend from the towering mast of Schooner America 2.0 to welcome in 2024. The fun starts in the afternoon with...Read more
great gatsby plane drop


Dec 31 2023 - 11:15pm
Dress to impress in your best Gatsby era outfits at First Flight, Enjoy an open bar, champagne toasts, chef-manned stations and live band. At the stroke of midnight, a replica of an old Pan Am airplane with a real-life "stewardess" will take flight in the...Read more
sloppy joe's conch drop


Dec 31 2023 - 11:15pm
This year at Sloppy Joe's, the conch shell will drop at the approach of midnight for the 30th time at the corner of Duval and Greene Street to ring in the New Year! Watch it live in the street or watch from inside the bar...Read more
Key West Track & Field Club

Pole Vault In Paradise

Jan 6 2024 - 9:00am
Pole Vault in Paradise brings together pole vaulters of all ages to compete alongside some of the best pole vaulting elites from around the country. Sponsored by the nonprofit Key West Track & Field Club, the event is to be staged at Key West High...Read more
Florida Keys Seafood Festival

Florida Keys Seafood Festival

Jan 13 2024 - 8:00am to Jan 14 2024 - 8:00pm
Gather your entire family to savor the freshest seafood, sourced, cleaned, and expertly prepared by our local fishermen. The Florida Keys Seafood Festival serves as a fundraiser for the Florida Keys Commercial Fishermen's Association (FKCFA), with proceeds directed towards sustainable fishing initiatives, marine restoration endeavors,...Read more
Key West Half Marathon and 5K

Key West Half Marathon & 5K

Jan 12 2024 - 7:00am to Jan 15 2024 - 5:00pm
The Annual Key West Half Marathon & 5k is a "bucket list" race.Read more