May is a gorgeous month to visit Key West – the days are long, the sky is clear and the Royal Poinciana trees are ablaze in fiery orange blooms! As peak tourist season winds down, it’s as if the island catches its breath before school lets out and summer sets in.

On Your Mark, Get Set, PADDLE!

May 4

Grab a buddy and grab a board for this year’s Key West Paddle Classic! This event brings together all skill levels of the paddling arts including rowers, kayakers and paddleboarders who will engage in friendly competition over this 4-day event that includes a 12 mile circumnavigation of the island itself! Rather skip the paddling part? You can still participate in the lively proceedings surrounding the event like Happy Hour, great food and live music. So row, row, row your boat down to Higgs Beach and let the party begin!

Fury's Key West Ultimate Express

Spice Things up for Cinco de Mayo

May 5

Throw on your swimsuit and apply the sunblock, it’s time to hit the seas with Fury! Aboard our fleet of decked out catamarans you can celebrate Cinco de Mayo the way it was intended – on the water! We invite you to a Mexican fiesta like no other, with margaritas and delicious Mexican-style cuisine on select Fury trips. There’s no better way to enjoy the holiday and gorgeous May weather.

Fury sail boat with beautiful sunset in background

Songwriters Sunset Sails – Watch Live

May 8-12

Our Songwriters Festival Sunset Sails always sell out. However, for those of you that were unable to book in time, you can still get in on the action. Through the magic of Facebook Live, you won’t miss a beat as world-renowned songwriters like Aaron Scherz, Tyler Reeve, and Channing Wilson play their hits in an intimate setting with our famous Key West sunset providing back-up. Visit our Facebook page and follow us to receive notification when we go live. Unless the weather conditions are unfavorable, this special streaming event guarantees you a spot on our boat no matter how far away you may be so fire up the wireless, grab a cold one and enjoy all this great music from the privacy of your favorite chair.

Mother's Day with Fury Key West

Pamper Mom in Island Style

May 12

Make this a Mother’s Day she’ll never forget! For the mom who enjoys the relaxation of breakfast in bed, treat her to Fury’s Island Adventure trip. Grab your snorkeling equipment and dive into the warm, crystal blue waters. Then, lounge atop a paddleboard or kayak as you explore the lush mangroves of the Key West backcountry. And for the mom who has an adventurous side, skip the traditional brunch and embark on a full-day Ultimate Adventure trip. You won’t have to decide on the perfect gift because this trip includes everything from snorkeling, banana boat rides and parasailing to jet skiing and a water park. Not able to make it to Key West for Mother’s Day but still want to treat her to something unforgettable? Purchase a gift certificate for her favorite Fury trip.

Eat Fresh and Sustainable Local Seafood

If you like seafood, then you’ll love Florida stone crab claws! Though their thick, hard shell requires a little work and bit of finesse to crack, the taste is well worth the effort. These locally caught crustaceans pair perfectly with cold beer or white wine! And the best part – stone crabs are a sustainable fishery! After the claws are removed, crabs are returned to the water alive and their claws regenerate after a few seasons. The fishery closes May 15, so be sure to get them before then or you’ll have to wait until mid-October when it reopens.

Key West Whiskey Fest

May 24-27

You don’t have to hop a flight to the Emerald Isle or traverse the cliffs of the Scottish Highlands to attend a first-class whiskey tasting event. Lounge around the Southernmost Beach Resort in stunning Key West, Florida and soak up some of the most beautiful ocean views along with the flavors from the finest purveyors of whiskey in the U.S. Prominent national brands and small-batch varieties are all on hand with their latest offerings during this 4-day event where you’ll even get a chance to judge a cocktail competition. There will be flair bartenders wowing the crowd, live music, great island fare, merch tents, and a Whiskey Workshop where you’ll learn the subtle intricacies involved in making a world-class spirit! Best of all, a portion of the proceeds goes to support Keys Strong, an organization that helps prepare the Florida Keys against natural disasters.

Couple riding a jet ski in Key West

Rev up Your Memorial Day Weekend

May 25-27

Take advantage of the extended weekend with a trip to Key West. See the island from its best angle, on the water aboard a Sea Doo Jet Ski! During our Key West Jet Ski tour, you’ll explore our island while making stops at various points of interest behind one of our expert tour guides on a scenic 28-mile trip. It may not officially be summer yet, but local Conchs like to consider Memorial Day weekend as the kickoff to summertime. Don’t forget your waterproof camera so you can take pictures of famous Key West landmarks like Mallory Square and the Southernmost Point Buoy from a totally different, on-the-water perspective. And be sure to wave to the people on land who are no doubt taking pictures of you!

Splashin’ around with the locals 💦

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Enjoy Being a Minimalist at the Regatta

May 26

Key West hosts numerous boat races and regattas throughout the year, but none perhaps as colorful or memorable as the Schooner Wharf Minimal Regatta. You’ll be surprised by the crafty vessels participants are able to build with only one piece of plywood, two two-by-fours, a roll of duct tape and a pound of fasteners. The watercraft may not float long enough to complete the required course, but usually long enough for a photo opportunity! Costumed teams from local bars and restaurants vie for bragging rights in several categories.

Last Updated 06/17/2020