The perfect Key West sunset sail unfolds aboard the Appledore Star, a classic two-masted schooner designed for a quiet, romantic evening on the water. As warm breezes fill the sails, you’ll glide past the southernmost point of the U.S. and into Key West’s famous sunset—an experience ideal for couples celebrating honeymoons, anniversaries, or special moments together.
Enjoy premium wine, ice-cold beer, a full cocktail bar, soft drinks, and a chef’s selection of hors d’oeuvres and cocktail shrimp as the crew raises the sails. Guests are welcome to help hoist canvas or take a turn at the wheel aboard the only bugeye schooner in Key West, the last of its kind. With the sky glowing overhead, your sail passes Mallory Square, the Navy Mole, and historic Fort Zachary Taylor before returning gently to the harbor—an evening designed to be savored long after the sun slips below the horizon.
