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Best Events in Key West, May 2023

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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.


Mile Zero Fest


Called the ‘the friendliest and best fest’ out there by it’s attendees, Mile Zero takes their patrons to heart in every decision made. They bring the best of Red Dirt & Americana Music to Paradise every year. Official Dates for 2021 are April 27th – May 1st and the last day is sure to be a grand finale!


Pride Follies

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Pride Follies returns to headline this year’s PRIDE celebration presented by the Key West Business Guild. Fantasy Fest Queen Destiny Montgomery is to direct this year’s presentation of Key West talent not usually seen on a professional stage, at the Key West Theater, 512 Eaton St. Does open 7 p.m., show starts 8 p.m. Tickets available online for general admission, balcony and socially-distanced table seating.


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 5-9th) “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.


Finish Your Vacation Strong…With A STRONG Cocktail!


Finish a sunny day around Key West with a fun afternoon bar hopping on our Craft Cocktail Crawl. 


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!