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Key West Events

Holidays, festivals, outrageous parades and special occasions—you won’t find a more ‘event-full’ place than Key West, FL. From tropical spins on holidays such as 4th of July and Thanksgiving, to Key West signature events like Fantasy Fest and the Meeting of the Minds, be sure and check your calendar: If it’s sunny and warm in Key West, there’s bound to be a celebration!

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Valentine’s in Key West!

Have an adventure this Valentine’s Day in Key West with the one you love. Join Cool Key West for a perfect sunset sail, a romantic day sailing, snorkeling and kayaking, or go all out with jet ski tour around the island.

Easter in Key West

Where else in the world can you find the Easter Bunny hiding eggs 20-ft underwater …in full snorkel gear? (And where else can you find kids and adults who dive in after them?) It’s business as unusual here in the Florida Keys: Not only do we like our fun wet, we like our wet fun—Easter included!

Key West Songwriter’s Festival

Celebrate one of the most famous Key West events with an exclusive Sunset Cruise.

4th of July in Key West

4th of July, Key West-style means friends and families. Daytime fun, then hop aboard chartered boats to experience Key West’s most unforgettable fireworks display – from the water. These cruises are guaranteed to sell out, best to book in advance. May the Fourth be with you!

Key West Powerboat Races

Guaranteed to be one of the most thrilling experiences of your life, Key West Powerboat Races get more legendary and powerful every year. The one time of the year where our laidback Key West pace gives way to pulse-pounding speed. Why’d the chicken cross the road? 125-mph Key West Powerboat Races! This opportunity sells out every year, be sure to book early.

Thanksgiving in Key West

If the idea of another year’s Turkey Day seems a little routine, step things up this year by celebrating Thanksgiving in Key West. Sure we have the traditional stuff (gobble, gobble) but where else can you snorkeling the reef before Thanksgiving dinner? Or build an appetite on waverunners? Key West Thanksgiving—you’ll give thanks all for the fun!

Key West Lighted Boat Parade

When you are in Key West you know we are going to do it different. Case in point, the Key West Lighted Boat Parade. It’s a cross between regular Holiday tradition and a fully-nautical Electric Light Parade—with music! A flotilla decked out for festivities and fun. Ho ho ho, Decks and Bows with bows of holly: it’s the Key West Lighted Boat Parade!

Christmas in Key West

Wake up Christmas morning and throw open the sash …because it’s nice and warm outside! Here in Key West, we keep our ice in our tropical drinks, and the “white stuff” is just the sand between your toes in your flip-flops. Let the neighbors and in-laws carol in the snow: When it’s Christmas in Key West, we’re all listening to Jimmy Buffet covers at the beach!

New Year’s Eve in Key West

What better way to bring in the New Year than with an awesome water adventure with Cool Key West? Choose from one of our all-inclusive water sports packages, backcountry eco tours, or set sail into the night on a sunset cruise with complimentary drinks and snacks. At Cool Key West, we’ve gone the extra mile to help you bring in the new year in style. May you have a wonderful new year in Key West!

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