Key West

15 Best Key West Sailing & Catamaran Tours

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.

1.Key West Sunset Sail With Full Bar, Live Music & Hors Doeuvres

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.”

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2.Small-Group Key West Sunset Sail With Wine

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”

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4.Key West: Schooner America Sunset Sail With Bar & Hors Doeuvres

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.”

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5.Key West Dolphin Watch Sunset Sail With Premium Wine, and Tapas Pairings

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.”

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6.Key West Sunset Champagne Catamaran Cruise

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.”

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8.Key West Wild Dolphin Sail and Shallow-Water Snorkel

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…”

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10.Key West Parasailing Adventure

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.”

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11.Key West Snorkel and Sunset Sail: Rum N Reggae

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,…”

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12.Key West: 2-Hour Sunset Sail on Schooner America 2.0

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!”

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13.Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West

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…”

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15.Sunset Sail Cruise in Key West

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”

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5.0Key West Sunset Sail Aboard Legendary Schooner Appledore2 hours (approx.)$89.00 5.0Classic Key West Schooner Sunset Sail With Full Open Bar2 hours (approx.)$109.00 4.5Parasailing Over the Historic Key West Seaport1 hour (approx.)$49.95 5.0Key West Day Sail Aboard Schooner1 hour 30 minutes (approx.)$73.10 5.0Reef Snorkel & Sail Adventure From Key West3 hours (approx.)$79.00 4.5Key West Multi-Stop Reef Snorkeling Boat Tour by Catamaran3 hours (approx.)$79.95 5.0Sail, Snorkel, Kayak, Dolphins, and Lunch With Honest Eco4 hours 30 minutes (approx.)$156.00 4.7Key West: Sunset Party Cruise by Catamaran$80 4.5Key Wests Favorite Afternoon Dolphin Sail2 hours 30 minutes (approx.)$59.00 4.5Parasailing at Smathers Beach in Key West1 hour (approx.)$49.95 4.7Key West: 2-Hour Sunset Sail With Live Music2 hours$79 4.5Key West: Afternoon Catamaran Sail and Dolphin Watch2.5 hours$59 5.0Sunset Sail on Historic Schooner in Key West2 hours (approx.)$109.00 4.52 Hour Key West Mini Catamaran Eco Tour2 hours (approx.)$264.95 5.02-Hour Sunset Sailing With Wine In Stock Island2 hours (approx.)$125.00 4.7Key West: Parasailing Flights$85 5.0Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak5 hours (approx.)$119.00 5.0Schooner Appledore Day Sail With Full Bar in Key West2 hours (approx.)$79 5.0Private 2-Hour Wind and Wine Sunset Sail in Key West$4,000.00 4.5Key West Morning Snorkel Sail With Mimosas and Gourmet Breakfast3 hours (approx.)$49.00 4.5Private Key West Sunset Sail2 hours (approx.)$695.00 5.0Key West Parasailing: Ideal For Cruise Ship & Downtown Guests1 hour (approx.)$49.95 4.7Key West: Ultimate Parasailing Experience1 hour$84 4.5Captains Choice: Dolphin Watch Sunset Sail2.5 hours$89