Portland Schooner Co. | 1912
Cart 0


We are tied to the ocean. And when we go back to the sea, whether it is to sail or to watch - we are going back from whence we came.
— John F. Kennedy



Book a sail of a lifetime on one of our three historic Schooners

Schooner Wendameen 1912, Schooner Bagheera 1924  & Schooner Timberwind 1931

Sail with us from Portland, Maine's Old Port on an authentic sailing vessel steeped in history — and enjoy the cruise of a lifetime. BagheeraWendameen and Timberwind provide the perfect vantage point to enjoy some of Maine’s most beautiful sights and sounds — from the deck of a storied wooden schooner built in the early 20th century. For a morning, afternoon, sunset, or overnight windjammer adventure, from Portland Harbor through the pristine waters of Casco Bay and beyond, refresh your spirit and excite your soul with an unforgettable sail reminiscent of a simpler time.