Private sunset cruises in Key West from $80. Romantic sails, proposals, dinner cruises. Perfect for couples.
Browse ToursExperience Key West's most iconic moment—the legendary sunset—aboard a private sailing vessel. Our sunset cruises are perfect for romantic evenings, proposals, or simply watching nature's daily masterpiece from the water. From intimate two-hour sails to full-evening experiences with dinner service, each cruise is tailored to your group. Many operators offer special packages for proposals, anniversaries, and celebrations. You'll sail past Mallory Square and experience where the Gulf of Mexico meets the Atlantic Ocean. Most sunset cruises operate May through October, departing 5-7 PM depending on seasonal sunsets. Popular options include private sailing charters, catamaran experiences, and glass-bottom boats. Book in advance—during peak season, sunset cruises often sell out 1-2 days ahead.
The sail usually runs in light rain and other moderate weather situations. The only time we cancel a trip is in the even...
Check AvailabilityCoastal Living Magazine ranked Danger Charter’s Wind and Wine Sail one of the top two Sunset Sails in all of North Ame...
Check AvailabilityEnjoy front-row seats to a private sunset cruise around the historic Key West Harbor. Skip the crowd and explore the isl...
Check AvailabilityJoin us for a Sunset Celebration on "Casual Monday" and see the unobstructed Key West sunset on the water that everyone ...
Check AvailabilityOn this an exclusive PRIVATE "Sunset Sail." We take you through several extraordinary locations and watch the sun drop w...
Check AvailabilityEscape the hustle and bustle of everyday life and enjoy the crystal-clear waters, sandy shores, and breathtaking views o...
Check AvailabilityMorning sails between 9am and 12pm, (you let us know the best time in that window for you) and daysails (Afternoon 1: 1:...
Check AvailabilityJoin us for a memorable night with all the best of Key West rolled into one night. We start our sail later than normal ...
Check AvailabilityShe’s located at the prestigious 5-star Perry Hotel & Marina, where our guests are permitted to use all resort ameniti...
Check AvailabilityThis is also our famous clothing optional tour. Our (discreet) captains will take you to private areas where you can get...
Check AvailabilityExperience the ultimate sunset in Key West with a private sunset cruise aboard our custom tiki bar boats. Toast to the b...
Check AvailabilityExperience the magic of a Key West sunset from the tranquility of your own private charter, a perfect way to celebrate s...
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Key West Sandbar Tours