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...
Fantasy Fest Royal Coronation 2026
The Fantasy Fest Royal Coronation returns to the Coffee Butler Amphitheater on Friday, October 16, 2026, for one of the signature opening-night celebrations of Fantasy Fest in Key West. The dazzling t...
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 ...
Key West Center Console Boat Rental
Ibis Bay Water Sport
Rent a center console boat from Ibis Bay Water Sport and enjoy the freedom to explore Key West from the water. This rental is a good fit for visitors who want a flexible boating day with access to local waters, scenic cruising, and time on their own schedule.
Book now!
Key West Mini Cooper Convertible Rental
Key West Adventures
Cruise Key West in a Mini Cooper convertible rental from Key West Adventures. This stylish open-air rental is a fun way to explore the island, enjoy scenic streets, visit beaches, and make getting around town part of the experience.
Book now!
Key West Two-Hour Sunset Cruise
Peak Charters Key West
Enjoy a two-hour Key West sunset cruise with Peak Charters Key West. This evening charter is a relaxed way to experience golden-hour views, island breezes, and the famous Key West sunset from the water without committing to a longer trip.
Book now!