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“Great time!!! Awesome crew and entertainment!! Snacks were excellent 😊 Drinks, drinks and more drinks! Awesome sunset.”
★★★★★★★★★★
3,559 reviews2 hours (approx.)From $79.00by Sebago Key West
Check Availability →Read our full review →
Experience a relaxing sunset cruise in Key West with dinner, live music, and drinks included. Perfect for romantic evenings or lively gatherings.
★ 4.5“Captain and all the crew members were great. Bartenders were outstanding. I was invited into the wheelhouse and talked to Capt Mike for almost 20 minutes. Great night overall.”
★★★★★★★★★★
1,707 reviews2 hours (approx.)From $92.95by Sunset Watersports
Check Availability →Read our full review →
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“It was good. The guides were nice and accommodating. Had a good time and it was a good beginners ride.”
★★★★★★★★★★
1,683 reviews4 hours 30 minutes (approx.)From $115.00by Danger Charters
Check Availability →Read our full review →
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“The captain and crew were awesome. The wines were a great choice and the snacks were just the right amount. There was a vegan in our party and she had nothing but wine...no complaints! I recommend the danger boat..it's the best!!”
★★★★★★★★★★
1,366 reviews2 hours (approx.)From $125.00by Danger Charters
Check Availability →Read our full review →
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.”
★★★★★★★★★★
954 reviews2 hours (approx.)From $108.91by Dolphin Echo Inc. (Catamaran Echo)
Check Availability →Read our full review →
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
Check Availability →Read our full review →
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.”
★★★★★★★★★★
907 reviews1 hour 30 minutes (approx.)From $79.00by Floridays
Check Availability →Read our full review →
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 experience! Crew was very attentive and food and drinks hit the spot. Weather was a little iffy but cleared for a spectacular sunset.”
★★★★★★★★★★
804 reviews2 hours (approx.)From $122.59by Classic Harbor Line
Check Availability →Read our full review →
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“Wonderful experience, excellent hors d’oevres, drinks, beautiful sunset, well worth the price - would have liked to be under sail instead of engine for the trip”
★★★★★★★★★★
699 reviews2 hours 30 minutes (approx.)From $89.00by Sebago Key West
Check Availability →Read our full review →
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“We didn't get to go on this cruise. It got canceled. We got put on a different cruise with appetizers, open bar, and live music. It was fine. But, not what we signed up for. However at least we still got to go on a…”
★★★★★★★★★★
586 reviews1 hour 30 minutes (approx.)From $59.00by Sebago Key West
Check Availability →Read our full review →
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“It was a great experience - have seen something very similar in Puerto Rico during my visit. Wanted to take my family along for a ride and they loved it!”
★★★★★★★★★★
576 reviews1 hour 45 minutes to 2 hours (approx.)From $69.95by Fury Water Adventures
Check Availability →Read our full review →
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“The trip was amazing! We saw so many dolphins, they even came right up to the boat. The snorkeling was great too, and the crew was super fun and friendly! The sunset was incredible, and we saw dolphins again! Highly recommend! 😍”
★★★★★★★★★★
493 reviews3 hoursFrom $79by Sunset Watersports Key West
Check Availability →Read our full review →
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“Really nice cruise. snorkeling spot wasn't exceptionnal but best in the area. The bar was great, boat was a big catamaran and crew really knew what they were doing.”
★★★★★★★★★★
419 reviews3 hoursFrom $34by Fury Water Adventures
Check Availability →Read our full review →
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 crew did a great job! The pictures do this excursion justice!”
★★★★★★★★★★
418 reviews2 hoursFrom $79by Sunset Watersports Key West
Check Availability →Read our full review →
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“Great trip, as advertised. Crew was great, the reef was awesome, saw beautiful 🐠 . We enjoyed chatting with other passengers and ended with a gorgeous sunset.”
★★★★★★★★★★
370 reviews3 hours (approx.)From $59.95by Fury Water Adventures
Check Availability →Read our full review →
More Key West Sunset Sails