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“The crew were friendly and on top of filling our drinks. The music was good and he took requests. Our experience was great.”
★★★★★★★★★★
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“The boat tour was awesome! The Cajun food was yummy! The musician was Ok, nothing to get excited about.”
★★★★★★★★★★
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“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…”
★★★★★★★★★★
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“Brian and team were wonderful. We had a great time. They had some lovely wine and appetizers. The sunset was amazing as well.”
★★★★★★★★★★
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“It was super fun. Staff is great. Music was really good. Note that If you want to be able to sit get in line early.”
★★★★★★★★★★
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 foods and lots of it. Tremendous staff, we are all very helpful and courteous. Great time and beautiful sunset. True sailing experience.”
★★★★★★★★★★
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“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.”
★★★★★★★★★★
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“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!”
★★★★★★★★★★
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“Perfect sunset night travel. Enjoyed the education about the coral reef and our crew was a delight during the trip.”
★★★★★★★★★★
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“was really fun but disappointed to not see dolphins but understand there wild animals”
★★★★★★★★★★
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“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…”
★★★★★★★★★★
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“A wonderful sunset cruise to celebrate my birthday!”
★★★★★★★★★★
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“Awesome experience and great snorkeling! The crew and boat were great and the drinks and music were fantastic!”
★★★★★★★★★★
370 reviews3 hours (approx.)From $59.95by Fury Water Adventures
Check Availability →Read our full review →
More Key West Sunset Sails