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.
Jun05Snorkel 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 - June 26, 2026
Time: Friday's, varies by tour operator
Location: Off-Site (Catamaran / Key West waters)
Jun06Sunset Sails
There is nothing quite like a Key West sunset, and the second-best place to view one (after the Sunset Pier, of course) is out on the water.
Date: May 9, 2026 - June 27, 2026
Time: Saturday's, Varies (sunset)
Location: Off-Site (Key West waters)
Jun07World Class Fishing
The Florida Keys are known for amazing fishing. From the flats and shallows, sight fishing for permit, tarpon or bonefish or in the deeper waters of the backcountry, on the hunt for snapper, grouper or tuna.
Date: May 10, 2026 - June 28, 2026
Time: Sunday's, Varies by charter
Location: Off-Site (Florida Keys waters)
Jun09Double Dip Snorkel Trip
Explore the turquoise waters of the 3rd largest coral barrier reef, teeming with fish, coral, sea turtles and more.
Date: May 12, 2026 - June 30, 2026
Time: Tuesday's, 2:00 pm – 5:00 pm
Location: Off-Site (Catamaran / Key West reef)
Jun10Zero Duval Scavenger Hunt
Experience a one-of-a-kind, interactive scavenger hunt in the downtown area of Old Town, starting at Zero Duval.
Date: May 13, 2026 - June 24, 2026
Time: Wednesday's, 10:00 am – 12:00 pm
Location: Old Town Key West (starts at Zero Duval)
Jun11Haunted Tours
Explore the SPOOKY side of Key West with a haunted historical tour.
Date: May 14, 2026 - June 25, 2026
Time: Thursday evenings (varies by operator)
Location: Off-Site (Key West – walking or trolley tour)
Jun11Ocean Key Lime Bike Tour
Sightseeing the Key West way with a leisurely island bike tour that can be done in flip flops!
Date: May 14, 2026 - June 25, 2026
Time: Thursday's, 10:00 am – 12:00 pm
Location: Key West (guided bike tour)
Jun11Key West Farmers Market
Visit the Key West Farmers Market every Thursday at the Truman Waterfront.
Date: May 14, 2026 - June 25, 2026
Time: Thursday's, 2:00 pm – 7:00 pm
Location: Truman Waterfront
Jul23Hemingway Days
Fans of Ernest Hemingway’s literary greatness and vigorous life – including scores of bearded Hemingway look-alikes
Date: July 23 - 27, 2026
Time: Varies by event
Location: Key West (Sloppy Joe's Bar, 201 Duval St., and other venues)
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)
