Key West
The sailing trips: tall-masted schooners and modern cats running reef days, day sails and the sunset ritual. Wind has always been this island’s native engine.
Experience a memorable Key West sunset aboard a spacious catamaran with live music, premium drinks, and delicious hors d'oeuvres for a relaxing evening on the water.
Most Popular“We had a little issue with finding the meeting location but once we found “the pineapple “, it was smooth sailing (pun intended). The crew were awesome. The food and drinks were plentiful and the delightful.”
Experience Key West’s vibrant coral reef on a 3-hour snorkel sailing trip with professional guides, unlimited drinks, and friendly, knowledgeable crew.
“I booked this excursion for my birthday and it was AMAZING! Saw tons of fish, turtles, a dolphin, and manta ray! The reef was gorgeous, drinks were amazing, and the crew members were incredible! Would 1000/10 recommend this to anyone and I plan to book…”
Experience a cozy sunset sail off Key West with wine, beer, and gourmet snacks. Perfect for relaxed travelers seeking scenic views and quality drinks.
“Wonderful experience even though there was not much wind the sails were up and the atmosphere and view were phenomenal. Great crew wine was flowing. Food was flowing was a wonderful experience that I would highly recommend.”
Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
“Windy and chilly but the crew made sure we had an enjoyable sunset cruise! The night was a great time for my family.”
Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.
“Everything was great. Captain and crew were friendly and courteous. Sunset was awesome. Boat away from the dock in plenty of time to be well out to see the sunset. This is definitely worth to money. A repeatable adventure on our next KW trip.”
Experience a relaxing sunset sail in Key West aboard a classic schooner with complimentary drinks and hors d'oeuvres. Perfect for a romantic or scenic evening.
“Fun and good information! Fun to learn how the boat worked! The the Keys are beautiful and the water was great.”
Experience a full day of sailing, snorkeling, and kayaking in Key West with all-inclusive food, drinks, and expert guides. Perfect for active water lovers.
“Fun crew, insightful. Maximum characters and minimum characters are silly nobody needs this info here”
Experience a relaxing sunset sail in Key West with dolphin sightings, tapas, and premium wine. A cozy, scenic cruise perfect for nature lovers and foodies alike.
“This was the BEST dolphin cruise ever! Well worth the money. Sebago is the bomb!!🤗🥰 Will definitely do this cruise again!”
Experience Key West’s stunning sunset from a luxurious 69-ft catamaran, enjoying included wine, champagne, and scenic views in a relaxed, authentic setting.
“Had a wonderful time on this sunset cruise. Loved that they limit amount of people so wasn’t crowded at all.”
Discover the Key West Reef Snorkel & Sail Adventure, a small-group cruise offering stunning reef views, friendly guides, and great value for memorable water fun.
“Well organized. Lots of marine life at the reef. Team was knowledgeable, friendly and fun!!! We had a good time with guests too.”
Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.
“Great trip- note there’s no cell service beginning about 30 miles offshore. Nice crew - very cool tour of the fort.”
Experience soaring above Key West’s turquoise waters with a safe, fun parasailing trip—breathtaking views, friendly staff, and photos to remember.
“Captain Alex and Garrison were fabulous....they went beyond for us....I'm going to send another tip to them”
Experience snorkeling over Key West’s only living coral reef, followed by a sunset sail with reggae music and drinks, all for about $59 per person.
“Everything was good but no rum in punch my wife n I had 6 and 10 drinks apiece n we are lightweights we should have walked off like Capt jack sparrow”
Experience a stunning Key West sunset on a graceful schooner, enjoy drinks, hors d'oeuvres, and wildlife sightings—all in 2 relaxing hours.
“Fantastic sunset experience on a real sailing trip with cool drinks and even some really nice snacks! Very much recommended!”
Experience stunning Key West sunsets with lively music, unlimited open bar, and delicious appetizers on this 2-hour catamaran cruise for $79.95.
“The sunset, the drinks and the music were all great! Snacks were nothing special, but we planned ahead ate dinner. We have done a cruise like this before and it is usually a couple of veggies and maybe rolls or some kind of bite size…”
Schooners at sunset, reef by morning and Duval Street in between.