Portland Maine Schooner Sails

Portland’s schooner sails are run by Portland Schooner Co. from its dock house at the end of the Maine State Pier, past the Casco Bay Lines ferry terminal. Its public sails last two hours on Casco Bay, four times a day from May to October, the last one at sunset, on wooden schooners built in Maine, three of them on the National Register of Historic Places. You may bring your own food, beer and wine. The sails are not narrated, though the crew answers questions, and they stay in the sheltered waters of the bay, heading for Portland Head Light when the wind allows. The 2027 dates were not on sale yet (checked October 2026); the season starts in the first or second week of May.

Times and prices

Times and prices from Portland Schooner Co.’s own website, which prints no year on them, checked October 2026.

On the booking listings, the sunset sail is from $77 on GetYourGuide and the afternoon sail from $69 on Viator (checked October 2026). Both listings refund in full if you cancel at least 24 hours before; tickets bought from Portland Schooner Co. directly are not refundable unless the company cancels, though you can move to another day if there is space.

The boats

Portland Schooner Co. sails a fleet of wooden schooners, and it does not say in advance which one takes a given public sail:

• Wendameen: 88 feet, a John Alden design launched in East Boothbay in 1912, restored in the late 1980s and on the National Register of Historic Places.
• Bagheera: 72 feet, a John Alden design built in 1924 by Rice Brothers in East Boothbay, and the first boat of the fleet, brought home to Maine in 2002.
• Timberwind: a 96-foot two-masted schooner built in 1931 at Union Wharf in Portland, which served as the Portland pilot boat until 1969, also on the National Register.

Where you board and park

The main dock house is at the end of the Maine State Pier: walk past the Casco Bay Lines ferry terminal to the dock house to collect tickets. A second dock house is at Ocean Gateway, next to the visitor center and across Thames Street from the AC Hotel; your booking names which one. Arrive at least 15 minutes before. There is no parking on the piers; the nearest garage is the Ocean Gateway Garage.

On the water

The sails stay in the calm, protected water of Casco Bay rather than the open ocean, so seasickness is rare. With a fair wind the schooner heads for Portland Head Light; otherwise it sails northeast between the mainland and the Diamond Islands. You will see lighthouses, seals and seabirds; whales are very unlikely. The crew is glad of help hoisting the sails, and anyone can take the wheel.

• Bring: your own meal, beer or wine; there are heads on board and life jackets for adults and children.
• Ages: there is no minimum age, but every passenger, infants included, needs a ticket.
• Access: the schooners are not wheelchair accessible; tell the company if you need help boarding.
• Rain: they sail in light drizzle and cancel in a downpour.

Who should pick something else

• More lighthouses close in: Boothbay Harbor’s sails pass three; see Boothbay Harbor schooners.
• A schooner with a bar: Appledore II in Camden runs a cash bar; see Camden schooner cruises.
• A sunset sail in June or July: the sunset sails guide compares the evening departures on the coast.
• Days at sea: the multi-day windjammer cruises sail from Camden and Rockland.