Sail into history.
Come aboard an Appledore and experience a piece of true maritime tradition.
“Appledore” is the name of a series of 2-masted schooners hand-built by Herbert and Doris Smith. Named for Doris’ hometown of Appledore Island, off the coast of New England, the Smiths have written two books about their adventures circumnavigating the globe: Dreams of Natural Places and Sailing Three Oceans.
Sebago is proud to have two Appledores in our fleet. And Key West is the best place for sailing a schooner yacht in America. Sailing aboard a tall ship in our calm, turquoise waters provides our guests with a maritime experience unlike any other. Choose from a romantic Key West sunset sail; an afternoon sail; or a backcountry, all-day schooner adventure.
If you’re looking for a truly unique Key West sailing experience, join us for Key West’s annual Wrecker’s Cup. This regatta series is held the last Sunday of January, February, March, and April and re-enacts days gone by 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.
Meet our schooners.
The first, Appledore II, is the largest of the five Appledore Schooners and is considered a prime example of a traditional wooden schooner. She divides her time between Camden, Maine in the Summer and Key West, Florida in the Winter, sailing the 2,000 miles between the ports twice a year.
The second is Appledore Star. Originally christened the “Jenny Norman,” she was built in 1982 by legendary shipwright, Jim Richardson of Lloyds, Maryland. He wanted a boat that was easy to sail but with a historical design, and decided on a wooden two-masted bugeye schooner with a round stern. Jim spent his retirement years sailing the Jenny Norman on the Chesapeake Bay. Now that the wooden bugeye schooner calls Key West home, Sebago chose to rename her in keeping with the Appledore tradition. “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. 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.
Ready for a little history?
Schooners originated in Europe in the 17th century. Typically, these tall ships carried two masts, but could carry up to seven. In the 18th century, schooners became popular in America for their speed, ease of handling, and shallow draft. In the 19th century, as many as 2,000 schooners plied their trades on the Great Lakes. With the advent of engines, these exquisite ships faded from sight. Until the Smiths revived this glorious era of sailing.
Bugeye schooners were originally designed in the late 1800s for oyster dragging in Maryland’s Chesapeake Bay. Needing a shallow boat, log canoes were the first vessels used for oyster dredging, but proved 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 our Appledore Star, is the last known bugeye schooner ever built.