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“Great staff, fun apps and delish drinks. Boat is nice and big with plenty of room up top and the covered down below”
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.
“Friendly, knowledgable staff, excellent wine, plenty of options to drink aside from their wine. Ample amount food”
Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
“Not your usual review as our sunset cruise was cancelled by a freak raging windstorm. Just wanted to thank the team there at the pier that handled everything so professionally and quick. Rescheduling was offered but we had opt for cancellation as it was our…”
Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.
“The crew was professional and friendly! They made sure we were safe and happy! The sunset was beautiful and the crew gave photo suggestions. They were also knowledgeable about the area.”
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.
“great time and great crew. what fun. ffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffffff”
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.
“The crew are awesome, friendly and knowledgeable. The captain knows his stuff and provides education on how you can assure your safety and have a most enjoyable trip. He is a world class navigator and knows the Keys well.”
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.
“The host and hostess were phenomenal..the scenery with the sunset was worthwhile moment to say the least. I would do it 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.
“It was great with the cruise being the best. Viator is the best to deal with. They go above and beyond to help ensure your booking is first rate,”
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.
“Awesome people very attentive we all had a great time would do again next time we are in the keys thank you both”
Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.
“We saved the best for last! They all day trip to Dry Tortuga- everything was fantastic from the great crew to the food and bar! We had plenty of time to see the fort and snorkel and then enjoy the great ride back to a…”
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.
“Great time, awesome crew! Loved going at night to experience the sunset! Highly recommend! Family friendly.!”
Experience a stunning Key West sunset on a graceful schooner, enjoy drinks, hors d'oeuvres, and wildlife sightings—all in 2 relaxing hours.
“Our sunset sail on the Key West Schooner was truly unforgettable! Captain Janet, along with Dan, Tom, and Milo, were all incredibly attentive and friendly, making sure everyone was comfortable and having a great time. We enjoyed delicious canapés and drinks as we cruised, soaking…”
Experience stunning Key West sunsets with lively music, unlimited open bar, and delicious appetizers on this 2-hour catamaran cruise for $79.95.
“Boat and crew were fantastic and sunset was amazing. We appreciated that the boat turned several times so that all guests could get good views without moving. Huge bonus with multiple dolphin sightings. Drinks were good but food was just sub-par at best. This would…”
Schooners at sunset, reef by morning and Duval Street in between.