Windjammer Champagne Sunset Sail

Windjammer Champagne Sunset Sail

Special Event – Friday, April 26th at 3:30pm:

Join us for participation in this large scale, hilarious harbor battle pitting the Conch Republic’s Military Forces (Air Force, Army, and Navy) and Privateers of all shapes and sizes against their valiant foe, non-other than a United States Coast Guard Cutter. The good-natured foes represent the USCG Cutter Diligence, attacked on Apr. 23, 1982, by the Schooner Western Union, the first Flagship of the Conch Republic.

Please Note: Guest WILL GET WET from the water cannon used in this reenactment. Also, beverage service may be slightly less than normal as the crew participates in the battle!

The perfect Key West sunset sail. Picture yourself on the deck of a romantic 2-masted wooden schooner. Wind blowing in your hair, the tall ship sails into the sunset past the southernmost point of the U.S.A

Our tall ship was hand-built in the same tradition of schooners since the 1700s. This 86’ windjammer has circumnavigated the globe. Today the Appledore II gracefully skims into the Atlantic in search of the perfect sunset.

Feel the sense of adventure as the crew hoists the sails. Participate in this age-old tradition by helping raise the sails. Take a turn at the wheel and feel the exhilaration of being at the wheel of a traditional tall ship.

Summers are spent sailing around Camden, Maine and winters are here in tropical Key West. Twice a year Appledore II sails the 2,000 mile ocean voyage between her two homeports. Some of the crew on your tour have made this exciting journey – ask them about their adventures.

With the painted sky as an exquisite backdrop, your sunset sail takes you past Key West’s Historic Seaport, Mallory Square’s Sunset Celebration, the Navy Mole where the big ships dock and the civil war era Fort Zachary Taylor. Soak in these sights while enjoying a glass of bubbling champagne or boutique wine, tropical home-made sangria, an icy cold premium beer, full cocktail bar or soft drinks.

As the sun begins its fiery descent into the Atlantic, your captain carefully maneuvers the Appledore II into position to maximize your view of the setting sun.

Start your own Key West tradition tonight – a sunset sail Key West style on the historic Appledore II schooner will forever linger in your memories.



Wide decks with room to walk around

Generous seating

Up to 49 passengers for an intimate evening

A spacious head (bathroom)

What To Bring

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.