Events

Carlfest

November 20-23, 2025

Four days of rockin’ music, unique events, and general shenanigans all in the name of helping one of our own – who also happens to be on the of most well-loved AND talented musicians that Key West has ever seen! The one and only Caffeine Carl!

Annual POSH Gala

Thursday, December 4th 2024

Since 2012, the POSH event has raised over $150,000.00 for the Florida Keys SPCA. The event is a gala style affair encouraging guests to dress up and don their favorite fascinators. Silent auctions, raffle prizes, exquisite catering from Great Events and Catered Affairs, and live music will be part of the fun at this year’s event. Follow our Second Line at the end of the night to continue the party!

MILE 0 FEST

January 27 – 31, 2026

Key West’s only Red Dirt & Americana Music Festival

Mile 0 Fest is a Destination Festival. We factor the fan’s opinion into every decision we make. We bring the best of Red Dirt & Americana music to paradise in Key West every Year. At Mile 0 Fest, we bring together some of the most talented and renowned artists from across the country for a one-of-a-kind event that showcases the unique spirit of Key West. Our lineup is carefully curated to provide an unforgettable musical experience!

Just a Few Friends

August 28 – September 2, 2025

Celebrating the life & love of Jimmy Buffet

Join us for a four-day island celebration honoring Jimmy Buffett’s legacy with live music, food, fun, and unforgettable experiences in Key West. Embrace the spirit with the Just a Few Friends: Latitude Adjustment Hotel Package, your passport to an unforgettable Labor Day weekend in Key West. As a Latitude Adjustment Package Guest, you’ll receive first access to purchase tickets for our special events and activities, ensuring you don’t miss a single moment of the festivities. From intimate gatherings to lively celebrations, you’ll be at the heart of the action.