Key West

15 Best Key West Sunset Sails

The sunset sails: champagne decks, live music boats and the old wooden schooners, all facing the same direction at seven. Sunset is a scheduled event in Key West, and the boats beat the Mallory Square crowds to it.

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

“While the weather wasn’t the best, the crew made up for it! Grace and the Jordan’s took great care of us. Delicious appetizers and drinks.”

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3.Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset

Explore Key West's coast with a half-day tour featuring sailing, kayaking, snorkeling, and sunset views. Perfect for adventure lovers and nature enthusiasts.

★ 5.0

“I had a wonderful time with Nate, Molly, and Bible. They were very helpful, warm, hospitable. This is a great way to explore the natural side of the Keys. I definitely recommend it.”

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9.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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13.Key West: Reef Snorkeling with Drinks and Sunset Option

Experience snorkeling at North America's only living coral reef in Key West, with drinks and sunset options, on a spacious catamaran with friendly crew.

★ 4.4

“Excellent family friendly snorkeling trip. The staff was professional and helpful. Loved the hospitality and mimosas on the way back to shore. The boat was also well cleaned and maintained. Would definitely do this excursion again.”

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More Key West Sunset Sails

4.9Key West: Schooner Sunset Sail with Food & Drinks2 hours$122 4.5Sunset Sip and Sail Key West with Open Bar and Live Music2 hours (approx.)$72.00 5.0Sunset Sail Cruise in Key West2 hours (approx.)$95.00 5.0Key West Sunset Sail Aboard Legendary Schooner Appledore2 hours (approx.)$89.00 4.5Key West: Sunset Dinner Cruise with Open Bar & Live Music2 hours$92 5.0Classic Key West Schooner Sunset Sail with Full Open Bar2 hours (approx.)$109.00 5.0Key West Sushi Sunset Cruise with Complementary Drinks$75.00 4.7Key West: Sunset Sail with Live Band, Drinks, and Appetizers2 hours - 150 minutes$79 5.0Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar2 hours (approx.)$65.00 5.0Key West Tiki Bar Sunset Cruise (by the seat)2 hours (approx.)$80.58 4.5Key West Sunset Snorkel with Unlimited Draft Beer & Wine3 hours (approx.)$69.95 4.7Key West: 2-Hour Sunset Sail with Live Music2 hours$79 5.0Sunset Sail on Historic Schooner in Key West2 hours (approx.)$109.00 4.2Key West: Glass Bottom Boat Reef Tour with Sunset Option1.8 hours$69 5.02-Hour Sunset Sailing With Wine In Stock Island2 hours (approx.)$125.00 4.5Key West: Dolphin & Reef Snorkel Trip with Sunset Option3 hours$75 4.6Key West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks3 hours$69 4.5Key West: Private Sunset Cruise on an Authentic Tiki Bar Boat2 hours (approx.)$456.88 5.0Private Sunset Cruise around Key West2 hours (approx.)$400.00 5.0Historic 7-Mile Bridge Sunset Cruise in Marathon1 hour 30 minutes (approx.)$124.99 4.5Private Key West Sunset Sail2 hours (approx.)$695.00 4.5Captain’s Choice: Dolphin Watch Sunset Sail2.5 hours$89 4.5Dolphin Watch + Sunset Sail with Honest Eco3 hours (approx.)$117.17 5.0Reef Snorkel + Sandbar & Sunset Sail-Small Groups with Honest Eco4 hours 30 minutes (approx.)$143.05