Welcome Aboard Schooner Lazy Jack in Boothbay Harbor your Maine Vacation starts here. Join the Schooner crew for a 2hr. day sail or private charter adventure on Boothbay Harbor’s oldest windjammer. Help hoist sails or take a turn at the wheel as we set a course out past Burnt Island Light, Squirrel Island, Ram Island Light and the outer islands of Boothbay. Keep a sharp eye out for porpoise, Osprey, Bald Eagles, and harbor seals as we slip by local boats setting their pots or hauling in the lobster catch of the day.