Key West Events

There is something happening in Key West all year long.

Key West is home to a rotating calendar of annual events that keep the island buzzing. Finding the best activities means checking our calendar and seeing what appeals to you when you arrive.
Fantasy Fest in the Florida Keys

Fantasy Fest

This annual week of costumes, masquerades, parades and parties brings out the creative spirit of everyone who participates. Billed as a multi-venue, costume festival for grown-ups, Fantasy Fest is attended by tens of thousands of participants. The week of wild events culminates in the Fantasy Fest Parade and Street Fair.

Dating back to 1979, Fantasy Fest was the brainchild of local business owners looking to create events that would attract visitors to the once slow season of October. What started out as a simple parade has gradually morphed into Key West’s largest weeklong series of events which attracts people from all over the world. Get your creative juices flowing, work out you costume ideas and come to strut your stuff at Fantasy Fest.

superboat race in Key West, FL

Key West Super Boat Race

Experience the most powerful of water activities in Key West with the Super Boats International World Championships. Watch as the world’s biggest and fastest boats attain speeds of up to 180 mph over the six-mile course on the Gulf side of the island. Over the course of the season, from May to November, teams from all around the world compete in National Series Points races which eventually determine the overall winner. Most of the Super Boat racers are out on the water in a different locale every weekend. Take a shore side seat for this exciting watersport action.
Meeting of the Minds

Parrot Head Convention

Get your own little taste of Margaritaville by migrating to Key West along with the rest of the Parrot Heads. Parrot Head chapters from all over the world flock to Key West for an annual Meeting of The Minds, a four day convention that celebrates friendship, charitable “partying with a purpose” and Jimmy Buffet’s music. The Parrot Head convention annually attracts about 3,500 attendees on the week following Fantasy Fest and is regarded as one of the best things to do in Key West around the end of October.

Escape to Paradise

Savor the relaxed Key West vibes that permeate our chilled-out oasis in the heart of Key West.

DISCOVER OCEAN KEY RESORT

Escape to Paradise

Savor the relaxed Key West vibes that permeate our chilled-out oasis in the heart of Key West.

DISCOVER OCEAN KEY RESORT

PACKAGES & OFFERS

Sunny Side Up

The most desirable view (and way to wake up) on all of Key West.  Daily breakfast for two on the privacy of your balcony or down in our waterfront restaurant.

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Romance in Paradise

Indulge in the best oceanfront accommodations on the island and pamper yourselves. Champagne on arrival, $100 spa credit & $100 food and beverage credit – per day – per room.

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