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“Very friendly and knowledgeable staff. Despite windy and cloudy weather, we had an exceptional time. Hors d’oeuvres and drinks were delicious.”
Experience Key West’s vibrant coral reef on a 3-hour snorkel sailing trip with professional guides, unlimited drinks, and friendly, knowledgeable crew.
“The crew is great! They explained how to use the equipment and worked to make the experience a great one!”
Experience a cozy sunset sail off Key West with wine, beer, and gourmet snacks. Perfect for relaxed travelers seeking scenic views and quality drinks.
“Very attentive staff on the boat! Generous wine pouring. Nice variety. Beautiful cruise. Check in process was slow.”
Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
“Fun and drinks great band. Weather was good got to see the sunset it was a great experience highly recommend”
Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.
“Hunter and the Captain were Great Hosts. Made sure you are Hydrated Definitely recommend This 90 minute Sunset Tour”
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 experience! Crew members were the best and took care of everyone on board. The food and drink were great too!”
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.
“A nice way to get to do multiple activities at the same time. The snorkeling was better than my time at Cabo. All of our guides are great. Lots of food and drink.”
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.
“Captain Daniel and John were outstanding and very accommodating. The tapas were exceptional, much more than we anticipated and would give the chef 5 stars!”
Experience Key West’s stunning sunset from a luxurious 69-ft catamaran, enjoying included wine, champagne, and scenic views in a relaxed, authentic setting.
“It was above the expectation. Nice crews, open bar and live music were great. Only thing I could’ve done differently is bringing a sweatshirts. It was pretty chilly out in the sea.”
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.
“This was an awesome snorkeling experience!! The boat was small - about 12 passengers, and the crew, Chuck and Jared, were very friendly, welcoming and helpful! Compared to the mega boats, this was excellent for our first time snorkeling. We had a variety of ages…”
Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.
“Ben was a terrific tour guide! He knew so many facts and interesting stories about the fort. It is a fascinating place to visit.”
Experience soaring above Key West’s turquoise waters with a safe, fun parasailing trip—breathtaking views, friendly staff, and photos to remember.
“We did our first time parasailing with Fury and it was great! We did 9AM early bird tour. Captains (I forgot their names) were really experienced. Tow of our group were eldery (in their 70s and one of them had both knees surgery around a…”
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.
“I would’ve loved to appetizers. The staff energetic was great. Your out there for 3 hours with nothing to eat”
Experience a stunning Key West sunset on a graceful schooner, enjoy drinks, hors d'oeuvres, and wildlife sightings—all in 2 relaxing hours.
“Great crew, nice ship, food was great, drinks were cold. Awesome experience. No changes needed.”
Experience stunning Key West sunsets with lively music, unlimited open bar, and delicious appetizers on this 2-hour catamaran cruise for $79.95.
“The sliders should’ve been made into sandwiches. The roles should’ve been cut and prepared with the meat. more options of food. Captain and workers were very nice.”
Schooners at sunset, reef by morning and Duval Street in between.