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Best Events in Key West, May 2024

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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.


Singer Songwriter Festival


Join us for one of the best events of the year! Key West’s 28th Annual Singer Songwriters Festival is the largest of its kind in the world. Enjoy 5 days and nights of musical bliss, as you see and hear countless musicians at various locations throughout the island. Venues include beaches, boats, bars, resorts and historic theaters and the best part is most of the shows are FREE! Check here for more information.


Support Local Theater!


“Brooklyn 1942, two brothers, Jay and Arty must learn to live with their stern Grandma, their Aunt Bella, and their Uncle Louie, a henchman for some gangsters”. Watch some of Key West’s best local talent in this Pulitzer Prize winning play at the Waterfront Theater. Tickets sold here

Through May 11


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. 


Spend the day at Key West’s favorite beach.


Soak up the sun, listen to the waves and the wind blowing through the trees at Fort Zachary Taylor. Not only is this a beautiful beach where the Gulf of Mexico meets the Atlantic Ocean, it’s also got historical significance; this State Park is home to an old Civil War Fort. For just a few dollars per person you can explore the fort, swim in the turquoise waters, BBQ or have a picnic and watch a spectacular sunset while the sailboats float by. This is truly one of the island’s best spots to spend a day away from the hustle and bustle of Duval Street. Check here for more info.


Schooner Wharf Minimal Regatta

Participate in or watch from the safety of the dock, Key West’s wackiest boat race! Competitors are given a strict list of the most minimal supplies, hence the name: The Schooner Wharf Minimal Regatta. Participants are allowed a single sheet of 4-by-8-foot plywood, two 8-foot-long 2-by-4s, a pound of fasteners and a trusty roll of duct tape. Regatta rules even forbid the use of caulking or adhesives, though epoxy paint is permitted. The “sink or swim” challenge is a Memorial Day Weekend tradition in the Florida Keys, with Sunday’s fun scheduled to begin at 11 a.m. when teams can register at the Schooner Wharf Bar, 202 William St. May 26


Support our Local Reef

Join us for Reef Relief’s Luau to raise money for local reef conservation. Put on your most tropical attire and sip a few tasty beverages by the beach. Sounds like a perfect day to us!