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.
“we were put on a different cruise which was bigger , longer time , music and apps. the focus was on an obnoxious singer and drinking alcohol. sunset was beautiful, food was yummy, service a was great.”
Take a high-speed catamaran from Key West to Dry Tortugas National Park for fort history, snorkeling gear, and breakfast and lunch.
“Great operation, boat crew and amazing time at the park. You will enjoy it! Just be prepared for the downtime on the ferry there and back.”
Sail into Key West sunset on the Sandie Cat with unlimited open bar, light bites, and live music for about two hours.
“The captain and staff were super accommodating and the DJ was nice. We saw several dolphins right before sunset!”
Sail the Florida Keys and snorkel a coral reef on a small-group 54' yacht with drinks and gear included.
“This sailing and snorkeling trip was really fun. We saw sea turtles as we were sailing and sharks and fish out at the reef. Really fun time plus wine or beer on the way back to the dock.”
See sharks up close on a shaded Key West catamaran, plus turtles, stingrays, dolphins, and hands-on marine info from expert captains.
“We saw a lot of dolphins! Unfortunatetly not many shells on shell island even if you walk towards the ocean side. Great guides very friendly And genuine”
Sail the Florida Keys by catamaran from Key West, watch bottlenose dolphins, and enjoy unlimited beer, wine, sangria, and soft drinks.
“This tour was canceled. Please return my money.”
Ride a mini catamaran in Key West for 2 hours through mangroves and sandbars, with wildlife chances, small groups, and photo keepsakes.
“I am extremely disappointed with how my recent situation was handled. Due to circumstances completely outside of my control, I was unable to move forward with the service I paid for. Despite explaining the issue and providing context, I was denied a refund. What makes this even more frustrating is that I did everything on…”
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.”
