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.
Tats for TaTas 2026 | The Breast Event of the Year
Tats for TaTas at Tattoos & Scars Saloon – Key West’s Breast Cancer Awareness Event Wednesday, October 14, 2026 • 7:00 PM – 10:00 PMTattoos & Scars Saloon • 512 Greene Street, Key West, FL T...
Waterfront Playhouse Presents: The Rocky Horror Show 51st
The Rocky Horror Show (Encore) at Waterfront Playhouse: Celebrate 50 Years of Cult Classic Chaos October 14 – October 23, 2026 | Waterfront Playhouse, Mallory Square, Key West, FLTickets & Info: ...
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...
Key West Double Rider Scooter Rental
Island Style Ride
Get around Key West with a double rider scooter rental from Island Style Ride. This rental is a convenient option for two visitors who want an easy way to explore Old Town, beaches, restaurants, attractions, and scenic island streets without relying on parking-heavy car travel.
Book now!Key West Afternoon Sail, Snorkel, Kayak & Sunset Excursion
Danger Charters
Spend the afternoon on the water with Danger Charters on a Key West sail, snorkel, kayak, and sunset excursion. This trip combines classic sailing, shallow-water adventure, snorkeling, kayaking, and a sunset finish, making it a strong all-in-one option for visitors who want more than a simple boat ride.
Book now!
Key West 2-Door Jeep Rental
Key West Adventures
Explore Key West with a 2-door Jeep rental from Key West Adventures. This compact open-air rental is a fun way to cruise the island, visit beaches, explore scenic streets, and enjoy the freedom of having your own ride while in town.
Book now!