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Key West Events

Looking for things to do in Key West? Check out these local annual events.

There’s always something to do in Key West! As the last stop on the Overseas Highway, Key West is closer to Cuba than it is Miami - and you’ll be able to sense it by the feeling in the air. Once home to Ernest Hemingway, the nation’s southernmost city is peppered with tropical fruit trees while the ocean is never far away. Gather with the locals at Mallory Square to celebrate the sunset while being entertained by street performers and buskers.

Key West is home to a rotating calendar of annual events that keep that island buzzing year round. Finding the best activities in Key West means checking your schedule and seeing what appeals to you when you arrive. Unlike the past, there is no down season, there will always be something to keep you entertained.

Woman wearing wings at Fantasy Fest Key West.

Fantasy Fest

Oct 19 – 28, 2018

This annual week of costuming, masquerading, parading and partying brings out the creative spirit of locals and visitors alike. Billed as a multi-venue, costume festival for grown ups, Fantasy Fest turns Key West into a spectacle of masked processions, parties, contests and dances attended by tens of thousands of participants. The week of wild events culminates in the Fantasy Fest Parade and Street Fair. When looking for a hotel close to Fantasy Fest ground zero, Ocean Key Resort & Spa has you covered.

Dating back to 1979, Fantasy Fest was the brainchild of local business owners looking to create events and activities in Key West 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.

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Super Boat Race in Key West.

Key West Super Boat Race

November 4 – 11, 2018

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. Reserve a room now at Ocean Key Resort & Spa to ensure luxury accommodations close to the Key West Super Boat Race.

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. 2018 marks the 38th anniversary of the Key West World Championships. Take a shore side seat for this exciting watersport action.

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Meeting of the Minds Parrot Head Convention Key West.

Parrot Head Convention

Oct. 31 – Nov. 4, 2018

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 3500 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. Since the host hotel for the event is typically sold out well in advance, if you’re still looking for luxury accommodations near the Parrot Head convention, consider Ocean Key Resort & Spa.

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People running a marathon.

Key West Half Marathon & 5K Run

January 20, 2018

The Key West Half Marathon is a competitive 13.1 mile road race that’s been recognized by Runner’s World as one of the top 10 bucket list, destination half marathons. 2019 will mark the 21rst edition of the annual event. The course runs through the Old Town and along the Key West waterfront. Landmarks include Ernest Hemingway’s house, the Key West Lighthouse and the southernmost tip of the continental US.

If you’re looking for something easier on the knees, try the 5K run which is considered one of the top activities in Key West for non-competitive runners. The 5K course skips the lengthy waterfront, but still cruises along Duvall Street and passes by Mallory Square. Entertainment is provided along the course and afterwards there’s an awards ceremony and celebration. If you’re looking to participate or simply cheer on the runners, Ocean Key Resort & Spa is the top luxury resort close to Key West Half Marathon events.

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Aerial view of Key West.

Swim Around Key West

June 16, 2018

Swim Around Key West is a 12.5 mile race around the island. Going into its 43rd year, the idea for Swim Around Key West began in 1977 when a recreational swimmer attempted the circumnavigation. It took almost 13 hours. Today, the course record is just over 3 and a half hours! There is a $1000 prize for any first place swimmer who breaks the current record.

If you don’t fancy yourself an endurance swimmer, you can also participate by being a support kayaker. Support kayakers shadow a swimmer and carry any food, drinks or other supplies on the swimmer’s behalf while providing protection from other watercraft. An awards ceremony takes place after the race along with refreshments and raffle draws. If you’re looking for a popular water activity in Key West, the Swim Around Key West should be on your list.

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