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.
“We had a great time. The ride over was nice. Once there I would not waste too much time on the fort unless that is really your interest. The best part was the coral reef. Make sure you ask the team where is the best area to enter to see the coral read. Amazing fish…”
A 2-hour Key West sunset sail on the Sandie Cat with an open bar, finger foods, and live music on the upper deck.
“Beautiful cruise and an amazing sunset. We enjoyed the food, drinks and music”
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.
“As advertised! Had a great time! Cost was very reasonable. Would do it again. Provider did excellent job.”
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.
“It was a wonderful experience. There were only 9 people on the cruise so it was quite cozy. The captain Alexa took us directly to an area where dolphins were plaint and jumping out of the eaters while Heather told us all about them. Heather also cut up fresh fruit and vegetables for us to…”
Sail from Marathon into Florida Keys National Marine Sanctuary for dolphins, Boot Key Harbor moorings, and a Sombrero Lighthouse photo stop.
“Mike is a great captain with amazing stories. Fun to learn from a true sailor. Beautiful boat and lovely spot.”
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.
“Great time and awesome crew! We were able to drop off wine and snacks and they put in the cooler for us. Enjoyed chatting with them. Boat was great.”
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.
