Key West Events

There is always something lively happening in old town Key West!

Key West is home to a rotating calendar of annual events that keep the island buzzing. Finding the best activities means checking our event calendar to see what might appeal to you when you arrive!

Fantasy Fest in the Florida Keys

Key West Fantasy Fest

Fantasy Fest is an annual 10-day party in paradise for grown-ups. Started in 1979 by a small group of Key West locals, the party was created to bring visitors to the island in what was a typically quiet, but beautiful season. It worked. Fantasy Fest has grown every year since its inception and is now the wildest extravaganza around! Fun-loving revelers from around the globe bring their creativity and imaginations as they descend upon Key West each year in October for 10 days filled with costuming, parades, libations, and excitement!

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 beginning of November.

superboat race in Key West, FL

Race World Offshore Key West Championships

Experience the most powerful of water activities in Key West with the Race World Offshore 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.

Marathon Near Ocean Key.

Key West Half Marathon & 5K

If you’re planning on joining the Key West half-marathon or 5k run, make Ocean Key Resort & Spa your home base. You’ll be able to relax before and after the race, in true Keys style. Be sure to book a massage after the race, to soothe your tired muscles!

Mile 0 Event At Sunset Pier.

Mile 0 Fest

Mile 0 Fest is a boutique destination festival. Called by attendees the ‘the friendliest and best fest’ out there. Bringing the best of “Red Dirt & Americana Music” to Paradise every year. Join us at venues around the island including the Sunset Pier!

Songwriter Event At Ocean Key Resort.

The Key West Songwriters Festival

The Key West Songwriters Festival is the largest festival of its kind in the world. Celebrating its 26th year. The festival revolves around five days and nights where live music bliss introduces crowds to the faces, voices and stories behind the songs. Join us at many venues around the island including the Sunset Pier!

Escape to Paradise

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

Escape to Paradise

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

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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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Gift Cards Now Available

Give the gift of adventure, exploration or relaxation in Key West. Gift cards to our resort, restaurant and spa are now available for purchase.

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