Sailing suits Key West better than any engine, and this list gathers the day sails and catamaran trips that earn it. Catamarans ride flatter than monohulls, a real mercy for anyone prone to seasickness. Reef stops and sandbar swims come standard on most full-day trips.
Experience the magic of a Key West sunset sail with a full bar, live music, and delicious hors d'oeuvres. Don't miss out on this unforgettable evening at sea!
Most Popular★ 4.5“Honestly worth all the money! Music 10/10, drinks were great & they were able to make mocktails to accommodate our pregnant family member! Food was good & they had plenty of it. They constantly came around to check on us & the views were amazing.”
★★★★★★★★★★
3,559 reviews2 hours (approx.)From $79.00by Sebago Key West
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Experience the ultimate Key West sunset sail with wine. Escape the crowds and enjoy a small-group adventure, sipping wine while taking in breathtaking views. Book now!
★ 5.0“Friendly, knowledgable staff, excellent wine, plenty of options to drink aside from their wine. Ample amount food”
★★★★★★★★★★
1,366 reviews2 hours (approx.)From $125.00by Danger Charters
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Experience the beauty of a sunset sail in Key West, complete with refreshing beverages. Don't miss out on this unforgettable adventure. Book your spot now!
★ 5.0“It was fabulous! This is my fourth time sailing with you guys and it was great! Great music, drinks, and conversation. So relaxing.”
★★★★★★★★★★
907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays
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Experience the breathtaking beauty of Key West at sunset aboard the Schooner America. Sip on cocktails, indulge in delicious hors d'oeuvres, and make memories that will last a lifetime.
“Great experience! Crew was very attentive and food and drinks hit the spot. Weather was a little iffy but cleared for a spectacular sunset.”
★★★★★★★★★★
804 reviews2 hours (approx.)From $122.59by Classic Harbor Line
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Experience the magic of Key West's dolphins while sipping premium wine and indulging in mouthwatering tapas. Join us for an unforgettable sunset sail like no other.
★ 4.5“The host and hostess were phenomenal..the scenery with the sunset was worthwhile moment to say the least. I would do it again.”
★★★★★★★★★★
699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West
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Experience the ultimate luxury on a Key West Sunset Champagne Catamaran Cruise. Sip champagne, soak in stunning views, and create unforgettable memories. Book your adventure now!
★ 4.5“We had a great time. DrewBear sang for us. That was great. The staff took great care of us. Loved it.”
★★★★★★★★★★
586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West
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Experience the vibrant underwater world of the Florida Keys on an unforgettable snorkel and sail adventure. Dive into adventure now!
★ 4.5“Well organized. Lots of marine life at the reef. Team was knowledgeable, friendly and fun!!! We had a good time with guests too.”
★★★★★★★★★★
540 reviews3 hours (approx.)From $79.00by Floridays
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Experience the thrill of sailing in Key West and snorkeling with wild dolphins in shallow waters. Book your adventure today and create memories that will last a lifetime.
★ 4.5“Great trip even with windy conditions! We got to the best snorkel spot for the day and then sailed around for the rest of the trip with cold drinks and great company. The crew made the most of the rough weather day and we couldn’t…”
★★★★★★★★★★
465 reviews4 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)
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Landmarks, history, and natural beauty collide in this captivating full-day catamaran adventure to the remote and enchanting Dry Tortugas National Park.
★ 4.5“Great trip- note there’s no cell service beginning about 30 miles offshore. Nice crew - very cool tour of the fort.”
★★★★★★★★★★
433 reviewsFrom $220.00by Historic Tours Of America - Dry Tortugas
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Experience the thrill of soaring above Key West's turquoise waters on an unforgettable parasailing adventure. Get ready for breathtaking views and an adrenaline rush like no other!
★ 5.0“It was a great time, well worth the cost.🦜🦎🦜. I would recommend this excursion to anyone. Will be back.”
★★★★★★★★★★
387 reviews50 minutes (approx.)From $53.70by Fury Water Adventures
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Discover the ultimate tropical adventure! Dive into crystal-clear waters, soak up the sun, and groove to reggae beats on a Key West Snorkel and Sunset Sail: Rum N Reggae tour.
“Good trip, but sail was not raised. Cap't said too much wind...(Saw many sailing) it was a 6' jump into the ocean, and a nerve wracking return to the boat via metal stairs being pounded w waves and no assistance. Good rum punch, efficient crew,…”
★★★★★★★★★★
370 reviews3 hours (approx.)From $59.95by Fury Water Adventures
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Experience a breathtaking sunset sail in Key West aboard the Schooner America 2.0. Enjoy a 2-hour cruise, beautiful views, and create memories that will last a lifetime.
★ 4.9“The sunset sail was wonderful. We saw a beautiful sunset on our cruise. We were treated to dolphin sightings. The crew was knowledgeable and it was such a thrill to watch them hoisting and lowering the sails. Drinks and snacks were provided. Highly recommended!”
★★★★★★★★★★
318 reviews2 hoursFrom $122by Classic Harbor Line - Key West
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Experience the magic of Key West's stunning sunsets while sipping on cocktails, dancing to live music, and indulging in delicious appetizers. Don't miss out on this unforgettable sunset sail!
★ 4.5“I’m not really sure if the vibe was supposed to be a fun party or a romantic sunset experience. The entertainment was a guitarist on the upper deck and his choice of music was something you’d find in a pub. This was not as fun…”
★★★★★★★★★★
314 reviews2 hours (approx.)From $72.00by Sunset Watersports
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Immerse yourself in the magic of Key West's sunset sailing trip with a secret ingredient that transforms the ordinary into something extraordinary...
★ 4.5“The captain and staff were super accommodating and the DJ was nice. We saw several dolphins right before sunset!”
★★★★★★★★★★
310 reviewsFrom $80by Sunset Watersports Key West
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Experience the breathtaking beauty of a Key West sunset on a sail cruise. Set sail for an unforgettable evening of romance and relaxation. Book now!
★ 5.0“Very good 💯 I love the crew very much love atmosphere the culture good experience Love crew very quiet and pleasant”
★★★★★★★★★★
260 reviews2 hours (approx.)From $95.00by Schooner Jolly II Rover
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