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Things to Do in Key West in May

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.

Race Around the Island on a Paddleboard

The island of Key West is relatively small, but if you’re one of the paddlers competing in the annual Key West Paddleboard Classic, the island suddenly seems a LOT bigger. Stand up paddlers, prone paddlers and kayakers come from across the country for this challenging, but oh-so-beautiful 12-mile race around Key West. There’s also a four-mile race for those not up for circumnavigating the island. The weekend also includes paddleboard clinics, a kids’ race and sprint and relay races. You’ll gain a greater appreciation for our “little” island when you see all 12 miles of its shoreline from the water, entirely on your own strength and stamina!

Fury's Key West Parasail Trip

Spice Things up for Cinco de Mayo

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's Commotion on the Ocean Sunset Cruise

Key West Songwriter’s Festival

The largest festival of it’s kind in the world, always located in Key West, includes 200+ Performers, 50+ Concerts for 5 full days and nights. Performances take place all over the island, from bars to boats, beachside to a historic theatre, it truly is a one-of-a-kind experience that brings locals together with performers and tourists from all over the world. Be sure to book a spot on our special Songwriters Festival Sunset Sails! Party with World-Renowned Songwriters.

Plan Your Own “Duval Crawl”

Start your night with a Commotion on the Ocean Sunset Cruise enjoying live music, bottomless beer, wine, and/or margaritas and witness the spectacular Key West Sunset. Then use our handy Google map to plot your crawl down Duval.

Mother's Day with Fury Key West

Pamper Mom in Island Style

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. Lounge atop a paddleboard or kayak as you explore the lush mangroves of the Key West backcountry. Then, grab your snorkeling equipment and dive into the warm, crystal blue waters. 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 and parasailing to jet skiing and kayaking. 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.

Rev up Your Memorial Day Weekend

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 remote mangrove islands in the backcountry and relax on a shallow water sandbar while following Fury’s expert guide 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!

Enjoy Being a Minimalist

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.

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Dolphin Watch Eco Tour Eco Tour • Backcountry Snorkel
  • 9:00am, 12:30pm
  • 3 hrs
  • low
  • Beverages
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Dolphin Watch Sunset Cruise Combo Eco Tour • Backcountry Snorkel • Sunset
  • 5:30pm
  • 3 hrs
  • low
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Double Dip Snorkel Sunset Combo Snorkel 2 Reef Locations
  • 5:30pm
  • 3 hrs
  • moderate
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Double Dip Snorkel Trip Snorkel 2 Reef Locations
  • 9:00am, 12:30pm
  • 3 hrs
  • moderate
  • Beverages
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Glass Bottom Boat Reef Eco Tour
  • 12:00pm, 2:00pm
  • 2 hrs
  • low
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Glass Bottom Boat & Sunset Cruise Reef Eco Tour • Sunset
  • 6:00pm
  • 2 hrs
  • low
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Island Adventure & Sunset Cruise Combo Eco Tour • Snorkel • Kayak • Paddleboard • Sunset
  • 4:00pm
  • 4.5 hrs
  • moderate
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Island Adventure Eco Tour Eco Tour • Snorkel • Kayak • Paddleboard
  • 9:30am
  • 4.5 hrs
  • moderate
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Key West Snorkeling Morning Reef Snorkel
  • 9:30am
  • 3 hrs
  • moderate
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Key West Sunset Cruise Sunset Cruise • Champagne
  • 6:30pm
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Land and Sail Package Trolley Tour • Sunset Sail
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Land and Sea Package Trolley Tour • Glass Bottom Boat
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$63.81 Reg. $77.90
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Reef & Ritas Snorkeling Trip Afternoon Reef Snorkel
  • 1:00pm
  • 3 hrs
  • moderate
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Rum & Reggae Afternoon Reef Snorkel • Sunset Sail
  • 5:03pm
  • 3 hrs
  • moderate
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