Discover the best festivals and events in Key West!
From captivating theater performances and comedy shows to exhilarating fishing tournaments and literary seminars, our curated event listings offer unforgettable experiences year-round. Plan your perfect Key West getaway and immerse yourself in the vibrant local culture, entertainment, and island charm.
Hedwig and the Angry Inch — Encore at Waterfront Playhouse
Hedwig and the Angry Inch Returns to Waterfront Playhouse Hedwig and the Angry Inch returns to the Waterfront Playhouse in Key West for an encore run from October 15 through October 23, 2026. This c...
Fantasy Fest 2026 – Musical Icons and Iconic Musicals
Fantasy Fest 2026 takes over Key West from October 16–25 with ten days of elaborate costumes, parades, live entertainment, street celebrations and some of the island's biggest annual parties. The 2026...
Zombie Bike Ride 2025 at Fort East Martello – Key West’s Halloween Parade on Wheels
Zombie Bike Ride 2026 at Fort East Martello – Key West’s Halloween Parade on Wheels Key West, FL – Sunday, October 18, 2026 The legendary Zombie Bike Ride 2026 returns to Key West for another unforg...
Fantasy Fest 5K Run/Walk
Are you ready for Fantasy Fest 2026? We are excited to be the Official Monday Night Party! Come RUN/WALK with us and see why it's More Than a 5K... It's a PARTY! This Bed-Time Stories and Magical Mon...
Pet Masquerade | Fantasy Fest 2026
Pet Masquerade at Coffee Butler Amphitheater – Fantasy Fest 2026 On Wednesday, October 21, 2026, the Coffee Butler Amphitheater will come alive with whimsy and laughter as the Pet Masquerade returns ...
Sloppy Joe’s 47th Annual Toga Party – Fantasy Fest 2026
One of the longest-running and most recognizable traditions of Fantasy Fest, the Sloppy Joe’s Toga Party transforms the legendary Duval Street bar into a sea of creative togas, outrageous costumes and...
Reef Revival Inaugural Lionfish Derby- All Day Fishing
The inaugural Reef Revival Lionfish Derby brings anglers and divers together in the Lower Florida Keys for a multi-day competition supporting marine conservation and Driftwood Ministries. The event b...
Key West Headdress Ball – 43rd Anniversary Edition
The 43rd Anniversary Edition of the Key West Headdress Ball returns Thursday, October 22, 2026, to the Coffee Butler Amphitheater at Truman Waterfront Park for one of the signature events of Key West ...
Captain Morgan Masquerade March 2026 – Fantasy Fest’s Locals’ Parade
The Captain Morgan Masquerade March, affectionately known as Fantasy Fest’s “Locals’ Parade,” takes over Old Town Key West on Friday, October 23, 2026, for one of the most colorful and participatory t...
Key West Private Combo Charter
Key West Coastal Charters
Build a flexible day on the water with a Key West private combo charter from Key West Coastal Charters. This charter is a good fit for visitors who want to mix island scenery, time on the water, and a customized boating experience instead of choosing just one activity.
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Key West Historic Seaport Food Tour
Key West Food Tours
Taste your way through the Key West Historic Seaport with Key West Food Tours. This guided food tour is a fun way to explore local flavors, waterfront history, and hidden culinary stops while learning more about one of the island’s most colorful neighborhoods.
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Key West Premium 6-Passenger Gas Cart Rental
Mile 0 Rentals
Explore Key West with a premium 6-passenger gas cart rental from Mile 0 Rentals. This larger cart is a convenient option for families or groups who want an easy way to cruise around the island, visit beaches, stop at attractions, and get around town together.
Book now!