Past Events

Key West Pride 2024

Celebrate PRIDE on a tropical island that is legendary for its laid-back style and its open and accepting atmosphere. Whether you’re looking to party with [...]

Hemingway 5K Sunset Run & Paddleboard Race

Runners, walkvers and paddleboard enthusiasts can test their skills and celebrate Ernest Hemingway’s sporting lifestyle Saturday, July 20th during the Hemingway 5k Sunset Run and [...]

27th Annual Key West Lobsterfest

A Celebration of our favorite Crustacean: August 8-11, 2024! Lobsterfest Schedule of Events August 8 - 11, 2024   Thurs Aug 8 Original Lobster Boil [...]

Inaugural Key West Rumfest

Presenting the 2024 Rum Fest  Welcome to America’s Southernmost continental Caribbean Island, What better place is there to celebrate RUM. August 16th is National Rum Day. [...]

Key West Brewfest 2024

Southernmost Beach Resort 1319 Duval Street, Key West, FL, United States

Brewfest is a multi-day festival hosted by Southernmost Beach Resort! It includes beer pairing dinners, pool parties, tap takeovers, and culminates with a signature tasting [...]

Key West Fantasy Fest 2024

Fantasy Fest 602 Greene Street, Key West, FL, United States

Key West Fantasy Fest 2024! Key West Fantasy Fest 2024 is an annual 10-day party in paradise for grown-ups! Started in 1979 by a small [...]

Schooner Wharf Bar 2024 Tree Trimming Party and Toy Drive

Schooner Wharf Bar 202 William St, Key West, FL, United States

Sunday, December 1 – FREE to Attend Schooner Wharf Bar 2024 Tree Trimming Party and Toy Drive Starting at 6:00PM LOCATION: Schooner Wharf Bar and Galley [...]

2024 Pet Pictures with Santa™ – Hosted by The All Animal Clinic

At the 16’ Nautical Christmas Tree on the Harbor Walk of Lights at William St.

Thursday, December 5 – FREE to attend 6:00pm – 8:00pm 2024 Pet Pictures with Santa™ – Hosted by The All Animal Clinic Professional photos by [...]

2024 Key West City “Hometown Holiday Parade”

2024 Key West City “Hometown Holiday Parade” SATURDAY, DECEMBER 7, 2024 - FREE! Starts at 6:30pm LOCATION: Parade starts on Truman Ave. (at White St.) then [...]

The Southernmost Regatta – 2025

The Southernmost Regatta - 2025 Top sailing teams from around the world compete in the azure waters off Key West, showcasing colorful sails and avid [...]

Key West Songwriters Festival 2025

The Key West Songwriters Festival is the largest festival of its kind in the world, and known as a career starter for top country talent. [...]

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