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Best Events in Key West, May 2020



What’s the buzz in Key West this May? From acting like a kid again to eating a bucket list menu island-style, we’re covering all the bases. Our list of things to do in Key West will have you drinkin’, dancin’ and playin’ like the locals.


Ready, Set, Paddle

Think you got what it takes? Challenge yourself with a 12-mile paddle around Key West. From May 2-5th there will be racing, paddle clinics, eco tours, happy hour, parties, great food, live music, raffles & more!  You can paddle solo or team up with friends and enter the 3-Person Stand-Up Relay Race!

Stay for Sunday FUNday and cruise out the Lazy Dogs on a leisurely boat ride to a secluded sandbar for a festive picnic!


Watch the Sculpture Parade

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We like to come up with any excuse to have a parade here in Key West and this one sounds pretty legit. The fourth annual Kinetic sculpture parade will feature human-powered sculpture art down Duval Street. It’s honoring Stanley Papio, a Key Largo metalworks artist from the 70s. The parade gets moving on May 4, 2017 @ 12:00 pm – 1:30 pm in front of Customs House.


Jam with G-Love

G. Love is coming back again on Tuesday May 7th! He’ll take the stage from 7-9pm at the at the Southernmost Beach Resort at the end of Duval st. The Ries Brothers will open for what should be a perfect night of sound waves and real ones. Tickets here!


Soak up the tunes at the Songwriters Festival

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Who writes all those songs you get stuck in your head? The Songwriter festival, celebrating it’s 24th year, spans five days (May 8-12th) “where live music bliss introduces crowds to the faces, voices and stories behind the songs.” With over 200+ artists performing live shows day and night, we’ll guarantee that you’ll be grooving while you’re here.


Satiate your cravings on a Seafood Lover’s Food Tour

Drinking Tour Florida

Drinking Tour Florida

Everyone knows there’s not much better than the fresh seafood of Key West, and this tour has done its due diligence to provide you with a top notch line-up of tastings. The Seafood Lover’s Tour not only showcases all of our different kinds of fruits of the sea (like local fish, pink shrimp, Florida lobster, & conch), but you’ll also get locally made beer, the regionally famous Key lime pie, and a knowledgable and entertaining local guide during the three hour tour.


Barbeque island-style on Memorial Day

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Photo: Rob O’neal

Party like the locals and head out into the sandbars in the Gulf of Mexico this Memorial Day. Make friends with some residents on the island and jump on their boat, or go on some ‘back-country’ or ‘eco-tours’ to see the pristine waters. But don’t forget what this day is about: remembering the vets who died while serving in our country’s armed forces!