Schooner Applejack was a renowned charter boat in the Bahamas from the 1950s until the late 60s. Sailing a route from Ipswich Mass, to Man O War Cay to Cuba this humble windjammer carried various cargos for her master, which included rum, guns, cigars, and passengers. Schooner Applejack takes its name from a watering hole, one of the builder’s favorite haunts in the Florida Keys. Today Schooner Applejack sails proudly from Boothbay Harbor carrying 14 passengers and is perfect for an intimate two-hour or private custom charter Sail Maine adventure.