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Backstage view of band playing Sunset Pier

Events

Just a Few Friends Key West

Just a Few Friends

September 3 - 7, 2026

Celebrating the life & love of Jimmy Buffett

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.

Parrot Heads celebrating in Just A Few Friends' annual parade down Duval Street in Key West
Mile 0 Fest

Mile 0 Fest

2027 DATES 

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!

Festival fans listening to Red Dirt music at the Key West Amphitheater during sunset.
POSH Gala

Annual POSH Gala

Thursday, December 4th 2025

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!

Two dogs wearing fascinators smiling from the Audubon House's porch
Carlfest

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!

Caffeine Carl shredding a guitar solo
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