Sailing in Key West

Select Local Merchants

Imagine the lightning-like stripe down the side of a yellowtail snapper or the marbled, almost serpentine pattern on a black grouper. The waters off the Florida Keys teem with such visually stunning marine life, and the crews of Gulfstream Fishing, Inc. know how to catch them. The Gulfstream IV, a 58-foot party boat that?s inspected twice a year by the US Coast Guard, motors approximately 60 passengers swiftly out to deep-sea fishing spots thanks to twin Detroit 8v92 turbo engines. Once anchored, the ship?s amenities?which range from men?s and women?s restrooms to a galley serving snacks?keep anglers comfortable between casts.

In addition to daily party outings, Gulfstream?s crews charter small-group trips that include evening shark fishing, offshore and inshore outings for trophies such as sailfish and tarpon, and trips onto coastal flats for catches such as bonefish and barracuda. They also organize private fishing charters to celebrate special occasions, such as a bachelor party or buying your first boat. An FAQ page answers many questions before guests head out.

1801 N Roosevelt Blvd
Key West,
FL
US

Key West Sailing Adventures’ water-savvy ship hands charter passengers to pristine locales for sailing and snorkeling trips. The four-hour excursion outfits each set of up to six divers with all necessary underwater gear—including masks, snorkels, and stingray saddles—as they dive into local reefs. After four hours of subaqueous sightseeing, divers return to the ship’s deck for a two-hour sunset cruise, which chases the picturesque sinking of the nation’s southernmost sun. Excursions occur aboard the 37-foot O’Day sailboat, a solid vessel that avoids bobbling atop waves by practicing core-strengthening Pilates twice weekly. The ship’s galley comes fully stocked with snacks and soft drinks to tide over mid-ocean hunger pangs.

201 William St
Key West,
FL
US

Billy figured that with Key West's powdery beaches and paradisiacal waters, a business could grow itself if it supplied high-quality watersports rentals and guides who could unveil the beauty of the area. To that end, he began building a team and a fleet that would take guests on adventures both above and below water. Today, guides conduct jet-ski tours on Yamaha WaveRunners, as well as lead groups of kayakers and standup paddleboarders on tours that meander along the Atlantic, Caribbean, and Gulf of Mexico. They also lead underwater ventures, such as scuba diving and snorkeling to technicolor coral reefs and historic ships that have lost the will to float. Individual equipment rentals cater to guests who prefer independent explorations. It's this breadth of tours and rentals that has earned Barefoot Billy's a certificate of excellence from TripAdvisor.

1435 Simonton Street
Key West,
FL
US

To call the restoration of the High Tide a labor of love would be to greatly devalue the definition of "labor." The 33-foot sloop remained on land for almost a year and a half as a team, mostly volunteers, returned the 1978-construction vessel to like-new status. Now, with Captain Seth at its open cockpit, the High Tide dips its fiberglass hull back into the waters of Key West, unfurls its sails, and embarks for the horizon. Whether on trips to admire the sunset, snorkel in the Gulf of Mexico, or test a new brand of motion sickness medication, the sailboat provides noiseless passage, save for the flap of canvas on the breeze.

202 William Street
Key West,
FL
US

On many windy, sun-drenched days in the Florida Keys, an electric catamaran flying the colors of the America Sailing & Diving Club can be seen escorting revelers across ocean waves. Formed in 1973, the club brings together boat owners as well as nonowners who can set sail on the club’s fleet of sailboats that range in size from 22 feet to 44 feet, each designed to keep the club’s carbon footprint to a minimum. The club also offers courses that teach landlubbers basic sailing techniques, such as knot-tying skills so they needn’t fear that their loose engagement ring will fall overboard.

12399 Overseas Highway
Marathon Key,
FL
US

After Captain Chris Gruno escaped the chilly air of New Jersey and his desolate cubicle desk, he brought the Grouchy Turtle to the Florida Keys, where he now ferries patrons through tropical waters. The catamaran, a 33.5-foot-long boat with six rooms, can sleep up to four on overnight voyages and fit up to six passengers on daytime jaunts. A blue, U-shaped bench borders the table in the saloon, and the master cabin boasts a bed big enough for a queen. The vessel is the vehicle for diverse aquatic jaunts, including kayak tours.

Boatman’s Mangrove Marina
Tavernier,
FL
US