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Have you ever dreamed of sailing around the world in your hand-built boat? Herbert and Doris Smith did just that, helping build a series of 2-masted schooners and circumnavigating the globe. The Smith’s named their series of schooners after Doris’ hometown, Appledore Island, off the New England coast.

Herbert and Doris wrote two books about exploring the world on their Appledores: Dreams of Natural Places and Sailing Three Oceans. On their first Appledore, they explored the Caribbean. Their oldest child was born in Key West during this sailing expedition, making Key West a fitting home port for the Appledore II.

Appledore II is the largest of the five Appledore Schooners and is considered a prime example of a historical traditional wooden schooner. Dividing her time between Camden, Maine in the summer and Key West, Florida in the winter, Appledore II sails the 2,000 miles twice a year between the two ports.

Schooners originated in Europe in the 17th century with a typical tall ship carrying 2-masts but having as many as 7. In the 18th century, schooners became popular in America for their speed, ease of handling and shallow draft. As many as 2,000 schooners plied their trades on the Great Lakes during the 19th century. With the advent of engines, these exquisite ships faded from sight. The Appledore II was designed by the Smith’s in the tradition of a 2-masted wooden schooner.

Appledore Star is the newest addition to Sebago’s wooden schooner fleet. Originally named the Jenny Norman, she was built in 1982 by legendary shipwright, Jim Richardson of Lloyds, Maryland. Wanting a boat that was easy to sail but with a historical design, he decided on a wooden two-masted bugeye schooner with a round stern. Jim spent his retirement years sailing the Jenny Norman on Chesapeake Bay. Since 2000, the bugeye schooner ran charters under the name Lucky Finn in New England waters.

Now that the wooden bugeye schooner calls Key West home, Sebago has chosen to rename the boat in keeping with the Appledore identity. Appledore Star is derived from two of the islands that make up the Isle of Shoals straddling the Maine - New Hampshire border. Appledore is the largest of these islands in Maine and Star Island is the largest in New Hampshire.

Bugeye schooners were originally designed in the late 1800s for oyster dragging in Chesapeake Bay, Maryland. Needing a shallow boat, log canoes were originally used for oyster dredging but were too small. A centerboard design allowed the bugeye to sail in the bay’s shallow waters while a low bulwark made it easy to handle dredges and drag for oysters. As the oyster harvest declined, the bugeye schooner dropped out of favor and was replaced by the skipjack, a less expensive oyster dragging boat.

The Jenny Norman, now the Appledore Star, is the last known bugeye ever built. With her shallow draft, the Appledore Star is well suited to exploring Key West’s shallow waters and is the only bugeye schooner in Key West.

Come aboard an Appledore and re-live a piece of maritime history. Sebago is proud to offer Key West excursions on the historic 2-masted wooden Appledore II and the Appledore Star. Key West is the best place for sailing a schooner yacht in America. Sailing a tall ship on our turquoise calm waters, you will enjoy a true sailing experience like nothing else. Choose from romantic Key West sunset sails on a schooner, an afternoon schooner sail or a backcountry all-day adventure on a schooner.

For a really unique Key West sailing adventure, join us each year for Key West’s Wrecker’s Cup. This regatta is held the last Sunday each month of January, February, March, and April and re-enacts the days of old when ships raced to grounded wrecks on the shallow waters’ treacherous reefs. Salvage rights were awarded to the first captain to reach a stranded ship and made Key West one of America’s richest cities. Today, competition is just as fierce and you can join in on the exciting race. Appledore II is a regular participant, winning on several occasions, giving her crew and passengers bragging rights until the next competition.