Key West Nightlife
Fantasy Fest began in the late 1970s as a way to liven up the island’s tourism off-season. Now, almost 50 years later, the vibrant celebration of creativity, community and island magic continues. This 10-day festival brings artists, performers, vendors and “free spirits” from around the world to Key West, with parades, costumes and parties.
Key West Fantasy Fest
Key West Fantasy Fest is going to be lively this year! Charge your creative juices during the craziness that is Fantasy Fest, and enjoy some partying, playing and plain old having a great time! Fantasy Fest occurs near Halloween every year and is now one of the busiest times of the year in Key West. Thousands of people participate, bringing great costumes and great times.
Looking for fun accommodations in Key West near the heart of the action? Ocean Key Resort is your hotel. And when you’re not celebrating at Fantasy Fest, Ocean Key guests can relax at the foot of Duval Street, just steps from the action in a beautiful setting perched over the harbor.
What is Fantasy Fest?
Fantasy Fest is the premier costume and masked spectacle in South Florida. The 10-day themed festival for grown-ups includes street fairs, costumed processions, glamorous balls and over 60 parties, all culminating in the Fantasy Fest Parade on the penultimate day. As many as 75,000 partygoers participate in the festivities by expressing their creativity through costumes, partying and general excitement.
The origins of Fantasy Fest date back to 1979, when a group of business owners decided to come up with an event to attract visitors during the slow season. What began as a simple, yet audacious costume parade has since turned into a multi-day event. The festival has since added several events and activities that serve as fundraisers for community groups and non-profit organizations.
What to Do at Fantasy Fest
Fantasy Fest has a jam-packed, 10-day schedule that features parades, carnivals, pool parties, luaus, musical performances, open house events, dances, contests, balls, pub crawls and a whole lot more. To say that you won’t be at a loss for something to do at Fantasy Fest is an understatement.
Events can be attended depending on your choice of costume (the Toga party, Bowties and Birthday Suits, Tutu Tuesday, the Venetian Masquerade Ball), activity (the Naughty Bike Ride, the Heroes and Villains 5k Run/Walk) or theme (Cheraoke, Beach Bash, Rock and Roll pool party.) In addition to festivities during the entire week, most of the attendees make sure to stick around for the final weekend for the Fantasy Fest Street Festival and Parade. Get your costumes ready and prepare to get weird!
Where to Eat and Drink
If you’re looking for some excellent dining near Fantasy Fest, check out the mélange of tastes from Florida and the Caribbean at Hot Tin Roof. Also open for breakfast, the restaurant offers beautiful harbor views overlooking the iconic Sunset Pier.
If you’re looking for some lighter fare, try the food at Sunset Pier Tiki Bar & Grill. The tropical Caribbean menu features seafood, burgers, sandwiches and fresh salads. Sip frozen tropical drinks while enjoying the nightly music, dancing and the most epic sunsets.
LIQUID is our poolside bar exclusive to hotel guests. Take pleasure in luxury VIP service, a dipping pool for cooling off and a large whirlpool for extra relaxation. Offering the best views on the island along with a premium cocktail bar and snacking menu, LIQUID is a delightfully secluded spot.
Where to Stay
Staying at the Ocean Key Resort, close to Fantasy Fest in Key West, means you can enjoy all of the crazy activities without a long walk. And when you’re not celebrating, relax in your Keys chic room with a balcony overlooking the water.
Events Calendar
Good times and good vibes are always on deck. Check out our activities and the local music scene at Ocean Key Resort and Sunset Pier.
Jul30Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - July 31, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Jul31Snorkel Experience
Dive into the 3rd largest coral barrier reef in the world and the only barrier reef in the continental United States.
Date: May 8 - July 31, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Oct16Fantasy Fest
Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands.
Date: October 16 -25, 2026
Time: Varies by event
Location: Key West (multiple venues)
Oct17That Arena Rock Show
Kick of Fantasy Fest 2026 with iconic rock music over the water on the world-famous Sunset Pier.
Date: October 17 & 18, 2026
Time: 7:00 PM
Location: Sunset Pier
- Oct20
Tay Tay Tuesday, Life of a Showgirl
Join us for a family-friendly tribute to your favorite musical icon and showgirl.
Date: October 20, 2026
Time: 6:00 PM
Location: SpaTerre
Oct2326th Annual Living Art Expo
A showcase of the human form as a living canvas.
Date: October 23, 2026
Time: 8:00 PM
Location: Sunset Pier
Nov01Race World Offshore Championships
Experience the most powerful of water activities in Key West with the Race World Offshore World Championships.
Date: November 1 - 8, 2026
Time: Daytime (race schedule varies)
Location: Key West (Gulf side – six-mile course)
Nov06Key West Powerboat Races – General Admission
Join us at the BEST VIEWING spot in town for the 2026 Race World Offshore, Key West World Championship.
Date: Friday, Nov 6 & Sunday, Nov 9, 2026
Time: 9:00 am - 4:00 pm
Location: Sunset Pier
Jan26Mile 0 Fest
Experience the “friendliest festival” in paradise, featuring the best Red Dirt and Americana music at island venues, including Sunset Pier.
Date: January 26, 2027 - January 30, 2027
Time: All day
Location: Key West (multiple venues)
Apr28Key West Songwriter Festival
Discover the stories behind the songs at the world’s largest songwriters festival, featuring five days of live music, including shows at Sunset Pier.
Date: April 28, 2027 - May 2, 2027
Time: All Day
Location: Key West (multiple venues)
