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

“It is a wonderful experience! Great music, food & beverages! The sunset was magnificent!! Highly recommend!”

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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

“Wonderful variety of water sports to do. Micah, Anthony, and Laura were very knowledgeable about the wildlife that was seen during our trip. Would definitely recommend to anyone who is up to being on the water!”

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7.Sunset Sail in Key West with Beverages Included

Experience a tranquil sunset from a small sailboat off Key West, with drinks included, attentive crew, and stunning water views—ideal for relaxed evenings.

★ 5.0

“Great night of sailing with a gracious captain and crew. They took great care of us making sure we had everything we needed! It was a lovely night.”

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14.Key West Signature Sunset Cruise with Open Bar, Food & Music

Experience stunning Key West sunsets on a 2-hour catamaran cruise with open bar, delicious appetizers, and lively music—perfect for a laid-back evening.

★ 4.5

“It was really cool to see the sun kiss the horizon. Definitely come hungry and ready to drink. The bartenders were great. DJ was awesome. My friend enjoyed the drinks and food. I enjoyed the view and sailing more than anything.”

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15.Key West Rum and Reggae: Reef Snorkel Adventure and Sunset Sail

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.

★ 4.5

“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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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