Skip to main content
CallReserve
A bunch of people in the streets celebrating Fantasy Fest

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.

Exterior of Sloppy Joes Bar at night with a lot of foot traffic

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.

A dragon float for Fantasy Fest in the street new Ocean Key Resort

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.

A band on stage performing

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!

The patio ready for service at Hot Tin Roof

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.

An open concept room with a living space, bed area and a balcony

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.

  • 2 people on a Fury Snorkel
    Sep08

    Double 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 - December 31, 2026

    Time: Tuesday's, 2:00 pm – 5:00 pm

    Location: Off-Site (Catamaran / Key West reef)

  • A lantern in the ground in a dark room and a ominous shadow in the background
    Sep10

    Haunted Tours

    Explore the SPOOKY side of Key West with a haunted historical tour.

    Date: May 14, 2026 - December 31, 2026

    Time: Thursday evenings (varies by operator)

    Location: Off-Site (Key West – walking or trolley tour)

  • 3 people biking on a Key Lime Bike tour
    Sep10

    Ocean 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 - December 31, 2026

    Time: Thursday's, 10:00 am – 12:00 pm

    Location: Key West (guided bike tour)

  • A mix of fruit at the Farmer's Market
    Sep10

    Key West Farmers Market

    Visit the Key West Farmers Market every Thursday at the Truman Waterfront.

    Date: May 14, 2026 - December 31, 2026

    Time: Thursday's, 2:00 pm – 7:00 pm

    Location: Truman Waterfront

  • A woman snorkelling with a sail boat in the water
    Sep11

    Snorkel 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 - December 31, 2026

    Time: Friday's, varies by tour operator

    Location: Off-Site (Catamaran / Key West waters)

  • 2 large sailboats on the water during a gorgeous sunset
    Sep12

    Sunset 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 - December 31, 2026

    Time: Saturday's, Varies (sunset)

    Location: Off-Site (Key West waters)

  • A man offshore fishing
    Sep13

    World 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 - December 31, 2026

    Time: Sunday's, Varies by charter

    Location: Off-Site (Florida Keys waters)

  • A parade in the streets for Fantasy Fest
    Oct16

    Fantasy 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)

  • The pier at night during Bahamas Benefit Concert 65
    Oct17

    That 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

  • Tamara Roper Romp
    Oct19

    Mrs. Roper Romp, Costume Contest

    Get your caftans ready and that signature curly red wig for a groovy costume party on Sunset Pier.

    Date: October 19, 2026

    Time: 5:00 PM

    Location: Sunset Pier