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Things To Do in Key West in May

May is a great time of year to visit to Key West. It’s the height of spring with summer just around the corner and the weather is glorious. The seas are flat and calm making it a joy to get offshore and the temperatures on land haven’t yet reached their summertime steamy peak. There are also a few of the year’s best events taking place. For the water sports enthusiast, the Key West Paddleboard Classic is from May 1-4, and for the music lover the Key West Songwriters Festival from May 7-11 is not to be missed.

Key West Paddleboard Classic, May 1-4

Test your endurance on this 12-mile race circumnavigating the island of Key West. Racers will get the full lay of the land as they paddle past the historic seaport, through mangroves and along the Atlantic shoreline. The race is open to paddlers, standup paddle boards, prone boards, outrigger canoes, dory boats, surf skis and kayaks. There will also be a 4-mile open race for those not quite up for the paddle around the island and plenty of events, clinics and happy hours will also be hosted over the course of the long weekend.

Endless Margaritas Cinco de Mayo Party, May 5

Who needs an excuse to indulge in endless margaritas in Key West? After all, this is the island that inspired “Margaritaville?” Still, nothing says margaritas quite like Cinco de Mayo. Start your celebration with a sunset party aboard Fury Water Adventures with endless margaritas, snacks and all the refreshments you can imagine on a beautiful sunset sail. Once you’re back on solid land, try one of the island’s favorite Mexican restaurants: Amigo’s Tortilla Bar, Bad Boy Burrito, Salsa Loca, Old Town Mexican or Chico’s Cantina. Bonus points if you hit all of them up on your trip!

Key West Songwriters Festival, May 7-11

For the country music fan, the Nashville aficionado or simply a lover of music, the Key West Songwriters Festival is a truly special annual event. The best songwriters in the nation (up and comers and legends alike) descend on Key West and its many bars and performance spaces for this festival that seems to get better every year. Look forward to big names like Sara Evans, Robert Earl Keen, Kacy Musgraves and Anders Osborn as the Smokin’ Tuna Saloon holds down the fort as the festival’s official headquarters. One of the most unique places to catch these live acts? Sailing aboard Fury Water Adventures at sunset. They’ll be hosting The Massacoustics, Jesse Rice, Blackjack Billy and more for three can’t-miss evenings on the water.