easy
2–3 hours
Suitable for most fitness levels; primarily relaxed seating with minimal physical activity required.
Enjoy a serene sunset sail with champagne on a classic schooner in Key West. Discover the perfect blend of relaxation, stunning views, and local history on this private adventure.
Luxurious Schooner Sunset Sail! | Available year-round
Experience the magic of a Key West sunset aboard the unique Appledore Star, the only bugeye schooner in the area. Enjoy a delightful selection of drinks and gourmet hors d'oeuvres as you sail past iconic landmarks, all while taking in breathtaking views of the sunset. Create unforgettable memories on this enchanting cruise.
- All Ages: Starting at $109.95
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 over the southernmost point of the U.S.
Soak in the sights while enjoying drinks and appetizers throughout your Key West sunset cruise. Included with your tour is champagne, boutique wine, Sebago’s famous home-made tropical sangria, ice cold premium beer and soft drinks. A chef’s selection of hors d’oeuvres and cocktail shrimp complete your perfect evening.
New this season - Now we're also featuring cocktails in our all-inclusive price. Sails up with a Schooner Appledore signature Bloody Mary or Dark & Stormy. Request your own favorite cocktail from our treasure chest of top-shelf brands, including Tito's, Crown Royal, Captain Morgan and Chandron Brut!
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 sailing schooner returns to Key West.
Start your own tradition tonight - a sunset sail Key West style on Sebago's historic bugeye schooner will forever linger in your memories.
Plan to arrive at least 15 minutes before departure to ensure a smooth check-in and boarding process.
Evenings on the water can be breezy; a light jacket or wrap will keep you comfortably warm.
For safety on the wet deck, choose footwear with good grip like boat shoes or sandals with sturdy soles.
Daytime sun can be strong; apply reef-safe sunscreen and bring sunglasses and a hat.
Key West’s maritime heritage extends back to the 1800s when schooners were essential for trade and transport across the Gulf and Caribbean.
Appledore supports marine conservation by promoting eco-friendly practices, including the use of reef-safe sunscreen and minimizing plastic waste on board.
Keeps you warm during cooler evenings on the water.
fall specific
Protects your skin while preserving the marine environment.
summer specific
Helps reduce glare from the water for a more comfortable sail.
Ensures safety and good footing on the schooner’s deck.