KEY WEST
Ranked by traveller popularity
The 10 most popular sailing in Key West. Here's what they actually deliver, who runs them, and what they cost.
Key West champagne sunset catamaran with beer, wine, champagne, sangria and light bites. 1.5 hours of captain-led views.
“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.”
Take a high-speed catamaran from Key West to Dry Tortugas National Park for fort history, snorkeling gear, and breakfast and lunch.
“Great trip- note there’s no cell service beginning about 30 miles offshore. Nice crew - very cool tour of the fort.”
Sail into Key West sunset on the Sandie Cat with unlimited open bar, light bites, and live music for about two hours.
“Beautiful cruise and an amazing sunset. We enjoyed the food, drinks and music”
Sail the Florida Keys and snorkel a coral reef on a small-group 54' yacht with drinks and gear included.
“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!!!”
See sharks up close on a shaded Key West catamaran, plus turtles, stingrays, dolphins, and hands-on marine info from expert captains.
Sail the Florida Keys by catamaran from Key West, watch bottlenose dolphins, and enjoy unlimited beer, wine, sangria, and soft drinks.
Ride a mini catamaran in Key West for 2 hours through mangroves and sandbars, with wildlife chances, small groups, and photo keepsakes.
“As advertised! Had a great time! Cost was very reasonable. Would do it again. Provider did excellent job.”
2-hour sunset sail from Stock Island with eight wines, five beers, and charcuterie. Small group, schooner crew, stunning views.
“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…”
3-hour Key West catamaran cruise for dolphins and sunset. BYOB, snacks and water included. Small group max 24.
“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…”
A 3-hour small-group sail in the Florida Keys National Marine Sanctuary from Marathon, with dolphin chances and Sombrero Lighthouse views.
“Mike is a great captain with amazing stories. Fun to learn from a true sailor. Beautiful boat and lovely spot.”
