KEY WEST · FLORIDA KEYS
Key West’s best days on the water.
The 8 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“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”
Spend a full day cruising on the Yankee Freedom III to Dry Tortugas, with Fort Jefferson history, snorkeling, and breakfast plus lunch included.
“Great trip- note there’s no cell service beginning about 30 miles offshore. Nice crew - very cool tour of the fort.”
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.
“It was a very fun experience especially as first time snorkelers. Enjoyed our time thoroughly. The captain and the co-captain were so helpful and entertaining! we loved the experience!!!”
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.
“We had a wonderful time on the Wind and Wine Sail! It was great meeting new people while enjoying delicious wine and tasty hors d’oeuvres. One of the highlights was seeing baby dolphins jumping out of the water—such a special surprise. The sunset was absolutely stunning, and the crew was incredibly attentive and knowledgeable throughout…”
Every way to get out on the water, and every reason to stay for the sunset.