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

“The crew were friendly and on top of filling our drinks. The music was good and he took requests. Our experience was great.”

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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

“This is well worth the $125 cost! The crew could not have been nicer or more accommodating! I was worried that it would be too cold to snorkel but there were wetsuits available for use. I had never been snorkeling before but it didn’t matter…”

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5.Adults only Sunset Cruise from Key West with Champagne

Experience a romantic adults-only sunset cruise from Key West with champagne, gourmet cheese, and stunning water views—perfect for a relaxed, intimate evening.

★ 5.0

“It's a fun way to enjoy the sunset. They had many selections besides Champagne and the crew was fabulous. I highly recommend this activity. The boat only seats a small group, and it was delightful.”

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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

“Wear comfortable shoes, it may get chilly in winter weather but a light sweatshirt is plenty to keep warm. The captain and fist Kate are very kind and well informed about sailing and Key West history.”

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8.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

“Great foods and lots of it. Tremendous staff, we are all very helpful and courteous. Great time and beautiful sunset. True sailing experience.”

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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

“The captains were great. The trip should have been canceled . The weather was rough saw 1 dolphin and no sunset. I would have rather had my money back or come another day to totally enjoy the experience.”

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10.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

“Beautiful sunset cruise aboard a catamaran. Crew super nice and accommodating making sure you are well taken care of. Plenty of O’douvres and drinks are served, along with live entertainment. Definitely recommend!”

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11.Key West Glass-Bottom Boat Tour with Sunset Option

Experience Key West’s vibrant coral reef from a glass-bottom boat, with options for daytime or sunset cruises, perfect for non-swimmers and reef lovers alike.

★ 4.0

“Perfect sunset night travel. Enjoyed the education about the coral reef and our crew was a delight during the trip.”

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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

“We had an amazing time on the Key West Snorkeling with Drinks and Sunset tour! From the moment we boarded, Captain Bill, Ally, Action Jackson, and Lauren made sure everyone felt welcome and excited for the adventure ahead. The crew was incredibly friendly, energetic, and…”

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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