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.
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!”
★★★★★★★★★★
3,559 reviews2 hours (approx.)From $79.00by Sebago Key West
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Experience a relaxing sunset cruise in Key West with dinner, live music, and drinks included. Perfect for romantic evenings or lively gatherings.
★ 4.5“Was very relaxing. If you wanted to be alone by yourself, you could. if you wanted to party with others you could. Good mix.”
★★★★★★★★★★
1,707 reviews2 hours (approx.)From $92.95by Sunset Watersports
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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“We had some weather come in while we were out. The Captain and crew did a great job keeping everyone safe and really made the best of it! We highly recommend this tour.”
★★★★★★★★★★
1,683 reviews4 hours 30 minutes (approx.)From $115.00by Danger Charters
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Experience a cozy sunset sail off Key West with wine, beer, and gourmet snacks. Perfect for relaxed travelers seeking scenic views and quality drinks.
★ 5.0“Quality sail on schooner with wine tasting and small plates. Paired well with fun staff. 5 stars all the way.”
★★★★★★★★★★
1,366 reviews2 hours (approx.)From $125.00by Danger Charters
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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“The crew was exceptional, as were the views of the sunset. I loved that this excursion was adults only and that my champagne glass was always full. Great find!”
★★★★★★★★★★
954 reviews2 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)
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Experience a vibrant sunset cruise in Key West with live music, unlimited drinks, and appetizers—perfect for relaxing and meeting new friends.
★ 4.5“This cruise was so much fun! The band was phenomenal! The crew worked non-stop serving drinks and making sure there was always plenty of appetizers available.”
★★★★★★★★★★
952 reviews2 hours (approx.)From $79.95by Fury Water Adventures
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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“There are bigger boats and longer trips and options out there for dinner cruises, etc. But we just wanted a nice 90 minute trek around the port with a small number of people on a sailboat. The bar service was a bonus to me. Captain…”
★★★★★★★★★★
907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays
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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 staff, fun and beautiful Can’t beat the views and the staff were engaging and a knowledgeable!”
★★★★★★★★★★
804 reviews2 hours (approx.)From $122.59by Classic Harbor Line
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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“Two of us did NOT get to go because we could NOT find a place to park!!!!!! Of course by that time we were charged!”
★★★★★★★★★★
699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West
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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“So much fun and the crew is fantastic!! If you do nothing else, DO THIS! I really can’t say enough good things. It’s just a really good time.”
★★★★★★★★★★
586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West
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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“We didn't get to the reef because of weather but they did take us to a spot on the gulf side that had some interesting coral, sponge, and fish, and narrated well. Not as good as seeing the reef but we won't be here tomorrow…”
★★★★★★★★★★
576 reviews1 hour 45 minutes to 2 hours (approx.)From $69.95by Fury Water Adventures
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Experience dolphin sightings, snorkeling in protected waters, and stunning sunsets on this 3-hour Key West cruise for $72. Perfect for nature lovers and sunset seekers.
★ 4.4“we went snorkeling and tried to catch a glimpse of dolphins for this trip. the reefs were ok but it was fun hanging out in the water. we were given 45 minutes to snorkel which was plenty of time. it was a little too windy…”
★★★★★★★★★★
493 reviews3 hoursFrom $79by Sunset Watersports Key West
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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“The water was super clear on the day we went and marine life was active. The crew were all very hospitable. Great trip!”
★★★★★★★★★★
419 reviews3 hoursFrom $34by Fury Water Adventures
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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“The ride and entertainment was great. We did not eat or drink but everything looked great.”
★★★★★★★★★★
418 reviews2 hoursFrom $79by Sunset Watersports Key West
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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,…”
★★★★★★★★★★
370 reviews3 hours (approx.)From $59.95by Fury Water Adventures
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