Category Archives: May Events

May 1-5– 18th Annual Key West Songwriter’s Festival

18th Annual Key West Songwriter’s Festival features more than one-hundred top songwriters performing at a variety of venues in Key West. There will be a concert on the Sunset Pier of the Ocean Key House at 1 Duval Street and … Continue reading

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May 27th- 21st Annual Minimal Regatta

Come check out the craziest regatta you’ll ever see. The 21st Annual Schooner Wharf Minimal Regatta takes place this Sunday, May 27th. This is a hysterical race of build-your-own boats using a minimum supply of materials. Prizes awarded for fastest … Continue reading

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May 26th- Reggae Moonsplash

It’s that time again!!! Reggae Moonsplash! This will be one incredible night filled with great food, great drinks, and of course the great sounds of Reggae. Come sit under the stars and in the sand at Higgs beach and enjoy … Continue reading

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May 19-20- Keys100

The 5th Annual Keys100 will be this weekend May 19-20. The three competitions are the individual races of 100 miles and the 50 mile race. The third race is the original South Florida six runner 100 mile relay race. The … Continue reading

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May 25th- Conga Line from Atlantic Ocean to the Gulf of Mexico

LET’S CONGA!!!!! On Friday May 25th revelers in Cuban attire will conga from the shores of the Atlantic Ocean to the Gulf of Mexico. This will be a celebration of Key West’s rich and colorful Cuban heritage. The conga line … Continue reading

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Stone Crab Season is coming to an End

Stone crab season ends tomorrow May 16th. If you have a good stone crab supplier or a favorite restaurant that serves them, you may want to get out your bibs and start cracking and slurping because they will be gone … Continue reading

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May 12- Key West Paddleboard Classic Race

The Annual Key West Paddleboard Classic Race will be May 12th at Smather’s Beach. The classic is organized by Key West locals with a passion for paddle boarding. A paddleboard is a sort of oversized, super-stable surfboard that allows you … Continue reading

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May 4th-13th- Key West Mystery Fest

Key West Mystery Fest kicks off today. 10 days of mysteries and mystery-related events will include: Crime Scene Photography – How long will it take you to solve the crimes? “Crime Scene Photographer” is an exciting, first-of-its-kind mystery game, custom-designed … Continue reading

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May 2-6- 17th Annual Songwriter’s Festival

The 17th Annual Key West Songwriter’s Festival will kick off tomorrow May 2nd. The festival revolves around 5 days and 5 nights of more than 20 free shows, staged at an array of the island’s most popular drinking holes and … Continue reading

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Upcoming Events

Summer is almost here and there are a plethora of things going on in Key West.  There are activities for everyone to enjoy. Some summer events include:  May 27– Cuban Heritage Festival–Join the conga line down mile-long Duval from ocean to … Continue reading

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