The perfect Key West sunset sail. Picture yourself on the deck of a romantic 2-masted schooner. Wind blowing in your hair, the tall ship sails into the sunset past the southernmost point of the U.S.A. Sunset aboard the Appledore Star is intended for couples and couples traveling together. This trip is designed specifically to cater to those on their honeymoon, celebrating an anniversary or other special occasion in Key West in a quiet, romantic setting. You won’t find loud music or guests playing their own music on this sail as we shy away from groups of 8 or more unless the boat is privately chartered.
Soak in the sights while enjoying drinks and appetizers throughout your Key West sunset cruise. Included with your tour is champagne, boutique wine, our famous home-made tropical sangria, ice cold beer, full cocktail bar and soft drinks. A chef’s selection of hors d’oeuvres and cocktail shrimp complete your perfect evening.
As the Appledore Star leaves the bustling Historic Seaport, the crew unfurls the sails. Satisfy your inner-sailor and help hoist the sails and take a turn at the wheel! You are sailing on a unique boat – the only bugeye schooner in Key West and the last known built ship of this oyster dragging bugeye design.
With the painted sky as an exquisite backdrop, your Key West sailing tour takes you past Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. During the sun’s fiery descent, your experienced captain maneuvers the Appledore Star into the perfect position for your viewing pleasure. While day turns to night, continue enjoying drinks and appetizers as your schooner returns to Key West.
Start your own tradition tonight – a sunset sail Key West style on our historic bugeye schooner will forever linger in your memories.
Wide decks with room to walk around
Maximum of 22 passengers for an intimate evening
Marine head (bathroom)
This is a Non-Smoking Tour
Grab your hat, sunglasses, camera and love of adventure. We will do the rest!
Please bring a valid, government issued photo ID. Some activities and enjoying alcoholic beverages require that we verify your age.
Welcome back! We are pleased to announce our official re-opening on June 5th with reduced capacities and additional safety protocols to ensure a safe and enjoyable experience for both passengers and crew. Advanced reservations (book Online or Call) are required. No walk ups are permitted per the City of Key West at this time.