KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 15 most popular sailing in Key West. What each trip costs, how long it runs, and who takes you out.
Sail Key West’s harbor to chase the champagne sunset from a 69-foot catamaran, with included drinks, a restroom, and great photo views.
Most Popular“It was great with the cruise being the best. Viator is the best to deal with. They go above and beyond to help ensure your booking is first rate,”
Spend a full day cruising on the Yankee Freedom III to Dry Tortugas, with Fort Jefferson history, snorkeling, and breakfast plus lunch included.
“One of the more beautiful beaches we have ever been to. Boat trip is five hours round trip so bring a book or games. But the island is well worth it. Take the tour. Crew was great. The guide was knowledgeable but not overwhelming.”
A 2-hour Key West sunset sail on the Sandie Cat with an open bar, finger foods, and live music on the upper deck.
“The crew did a great job! The pictures do this excursion justice!”
Sail off Key West on a 54 ft yacht for reef snorkeling. Small groups, included snorkeling gear, and drinks on the way back.
“Spectacular sailboat, knowledgeable crew, and great snorkeling. Drinks on the way back while reminiscing about the great underwater sights. So fun. Highly recommend!”
Two hours on the *Tiger Cat* for shark and wildlife viewing in Key West backcountry waters, with drinks, shade, and expert captains.
Cruise the Florida Keys on a 150-minute Key West catamaran dolphin watch with unlimited beer and sangria, roundtrip views included.
Ride a two-hour Key West mini catamaran eco tour through mangroves and sandbars, with a local guide and wildlife stops.
“Lots of fun. But you do need to be comfortable running a small boat by yourself in waves. Our guide was great.”
2-hour sunset sailing from Stock Island, Key West with wine, beer, and charcuterie on a small schooner crew by Danger Charters.
“This was an awesome experience. The food and wine selection was great! Staff was awesome! And the views of the sunset were top notch! Would highly recommend!”
Key West dolphin watch and sunset sail on a catamaran with organic snacks, reusable water bottles, and BYOB adult drinks.
“I booked for this event via Viator but unfortunately this event only takes place in winter as told by dock peoples when I shown my ticket”
Sail from Marathon into Florida Keys National Marine Sanctuary for dolphins, Boot Key Harbor moorings, and a Sombrero Lighthouse photo stop.
“If you are looking for a relaxing sail on a beautiful boat captained by the owner this is just the trip for you. The owner has actually taken this same boat on an around the world regatta! His stories and some of the photos he shared were amazing.”
Private 3-hour Key West catamaran for up to 6: sail the coast, snorkel West Sambo reef, spot dolphins and turtles, end with sunset.
“What a great day on the water! The captain, Nils, was super nice and took us where ever we wanted to go! The first mate, Simon…aka Chester, was a good sport, friendly, and super helpful! Ashley was very responsive to our questions! I HIGHLY recommend them for a great time!”
A private 90-minute sailing charter from Key West on High Tide, with a reef-cruise feel, wildlife refuge views, and a cheese platter.
“We took the private day sail on december 22, 2025 age range from 15 to 72 a family of 5. Will and Cameron were the best crew we could of possible had. The day was windier than normal so turned out to be excellent day for sailboating. They were very knowledgable and also alot of…”
Key West catamaran snorkel with open bar and Low Country seafood boil, plus premium gear and coaching. 4 hours of sun and salt.
Private 3-hour Key West sunset catamaran: snorkel West Sambo reef, spot dolphins and turtles, then cruise past Mallory Square.
“We spent New Year's Eve on a private catamaran trip with Captain Neils and his first mate Simon, and it was everything we could have hoped for. We got started a bit late (totally our fault), but Captain Neils kindly gave us extra time to make sure we still had the full experienRead more”
Key West 90-minute catamaran champagne sunset sail with open bar and prime views of Mallory Square, Sunset Key, and Fort Zachary Taylor.
Every way to get out on the water, and every reason to stay for the sunset.
