Key West

15 Best Key West Sailing & Catamaran Tours

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.

1.Key West Sunset Sail with Full Bar, Live Music and Hors D’oeuvres

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★ 4.5

“The captain and crew were extremely attentive to all of the passengers. They even brought drinks and horsdoeuvres to the passengers hanging out on the main deck who were watching the Amazing sunset. They even mingled with the everyone and helped take pictures when asked.…”

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2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

Experience Key West’s vibrant coral reef on a 3-hour snorkel sailing trip with professional guides, unlimited drinks, and friendly, knowledgeable crew.

★ 4.5

“Beautiful weather calm seas. Entertaining & knowledgeable captain & crew. Great experience on board. All equipment needed available & in great condition. Enjoyed hour at reef snorkeling. Bartenders make a great Rum punch & full bar. We will do again when we return to visit…”

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6.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

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.

★ 5.0

“Our captain, Janet was fantastic! She made sure our experience on her ship was perfect including the sunset. Her crew Jade, Milo & Heather were super efficient in not only tending to the ship’s duties but served their guests with a huge smile. Thanks for…”

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8.Key West Sunset Sail: Dolphin Watching, Wine, and Tapas

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.

★ 4.5

“This was the BEST dolphin cruise ever! Well worth the money. Sebago is the bomb!!🤗🥰 Will definitely do this cruise again!”

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9.Champagne Sunset Catamaran Cruise in Key West

Experience Key West’s stunning sunset from a luxurious 69-ft catamaran, enjoying included wine, champagne, and scenic views in a relaxed, authentic setting.

★ 4.5

“You may want a sweatshirt or light jacket after the sun sets. The wind is fairly strong and the temperature gets a little cooler. We booked a 1.5 hour champagne cruise but it didn’t sail that evening so we were given a complimentary upgrade to…”

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10.Key West Reef Snorkel & Sail Adventure

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.

★ 4.5

“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…”

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11.Dry Tortugas National Park Day Trip by Catamaran from Key West

Discover the beauty of Dry Tortugas with this full-day catamaran trip from Key West, featuring snorkeling, historic tours, and stunning ocean views.

★ 4.5

“We had a wonderful time. Mostly we enjoyed the walking tour with Dan. We learn the history and also all of past and present. A few stories also. Great job Dan! The ship’s crew out of their way to serve us and make sure we…”

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More Key West Sailing & Catamaran Tours

5.0Sunset Sail Cruise in Key West2 hours (approx.)$95.00 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 on Schooner America 2.0 with 2 Drinks1 hour 30 minutes (approx.)$73.10 5.0Key West Sailing & Snorkeling: A Reef Adventure3 hours (approx.)$79.00 5.0Kayak + Guided Snorkel & Morning Sail hosted by Honest Eco4 hours 30 minutes (approx.)$156.00 4.7Key West: Sunset Sail with Live Band, Drinks, and Appetizers2 hours - 150 minutes$79 4.8Key West: Shark and Wildlife Viewing Catamaran Tour2 hours$99 4.7Key West: Parasailing Above the Island Paradise1 hour$54 4.5Key West’s Favorite Afternoon Dolphin Sail2 hours 30 minutes (approx.)$59.00 4.5Parasailing in Key West at Smathers Beach1 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 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 4.5Key West Morning Snorkel Sail with Mimosas and Gourmet Breakfast3 hours (approx.)$49.00 5.0Parasail Adventure in Marathon$120.00 4.5Private Key West Sunset Sail2 hours (approx.)$695.00 5.0Key West Parasailing: Ideal For Cruise Ship & Downtown Guests1 hour (approx.)$49.95 4.5Captain’s Choice: Dolphin Watch Sunset Sail2.5 hours$89