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Sailing on a Maine Windjammer, the Schooner Heritage – Episode 1007

August 1, 2026

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In this episode of Amateur Traveler, I recount a six-night sailing voyage aboard the Schooner Heritage, one of the vessels in the Maine Windjammer Association fleet.

The trip began and ended in Rockland, Maine, and covered roughly 116 miles through Penobscot Bay. Unlike a conventional cruise, there was no fixed daily itinerary. Each day’s route depended on the wind, tides, currents, weather forecast, and the availability of a safe anchorage.

I was a guest of the Schooner Heritage. The cruise was hosted, while I paid for transportation to Rockland, expenses before boarding, and crew gratuities.

The Schooner Heritage

Heritage is a purpose-built passenger schooner designed and constructed by Captains Doug and Linda Lee. It was launched in Rockland in 1983 and later sold to Captains Ben Welzenbach and Sean Grimes, who had worked aboard for six sailing seasons.

Ben now serves primarily as captain, while Sean is both a captain and the ship’s cook.

Heritage is the largest vessel in the Maine Windjammer Association fleet. It measures approximately 145 feet overall, with a 92-foot deck, 15 passenger cabins, and room for up to 30 guests.

The schooner has red oak framing and planking, a white pine deck, and a Douglas fir mainmast nearly 80 feet tall. Including the upper rigging, the vessel reaches about 102 feet above the water.

Sailing from Rockland

Passengers can help raise the mainsail and foresail by hauling together on the lines.

Heritage does not have a conventional propulsion engine in its hull. Instead, it uses a diesel-powered yawl boat named Clark Kent to maneuver in harbors or push the schooner through calm water. An old two-stroke engine called Joe helps raise the anchor and hoist sails.

Our Route through Penobscot Bay

On the first sailing day, we crossed Penobscot Bay, passed through Fox Island Thoroughfare, and anchored near Kimball Island by Isle au Haut.

The following day, we sailed through Merchant Row and Jericho Bay to Burnt Coat Harbor on Swans Island, where passengers rowed ashore to visit the lighthouse and explore the island.

On Wednesday, we short-tacked through Jericho Bay before anchoring near Wreck Island, which became our “Lobster Island” for the day. The crew prepared a lobster bake over a wood fire, with hamburgers, hot dogs, corn, watermelon, and s’mores.

Thursday brought the most dramatic weather of the voyage. Thunderstorms and strong winds were forecast, so Captain Ben changed course and headed for the sheltered Carver Cove on Vinalhaven. We reached the anchorage, dropped the storm anchor, struck the sails, and secured the ship shortly before a powerful squall arrived.

Nearby windjammers reportedly suffered shredded foresails, but Heritage was safely anchored with its sails down.

On Friday, we enjoyed one of the best sailing days, crossing West Penobscot Bay and entering Pulpit Harbor after covering 26.8 nautical miles. Some passengers swam from the schooner, and Sean fired the ship’s cannon as a salute.

Life aboard Heritage

The cabins are compact, with upper and lower bunks, a sink with hot and cold water, reading lights, and electrical outlets. Two cabins have private heads, while the remaining passengers share three marine toilets on the main deck. There is one shower aboard.

Most of the day is spent on deck, reading, talking with fellow passengers, watching the crew, or simply enjoying the sound of the wind and water.

Cell service is inconsistent, and some anchorages have no reception.

Food aboard the Schooner

Food is a major part of the Heritage experience. Meals and baked goods are prepared in the galley using a wood-fired stove.

Breakfasts included blueberry pancakes, French toast, biscuits and eggs, blueberry buckle, banana coffee cake, and “boatmeal.”

Lunches included fish tacos, chili and cornbread, chicken soup with Anadama bread, turkey wraps, and minestrone.

Dinners included salmon with risotto, herb-crusted chicken, lasagna, pot roast, peach cobbler, homemade ice cream, and the island lobster bake.

The crew also produced a steady supply of cookies, brownies, breads, crab cakes, dips, and other snacks.

Practical Advice

Bring layers, rain gear, sunscreen, a hat with a strap, and two pairs of soft-soled, non-skid shoes. Soft-sided luggage is easier to store in the small cabins.

Heating appliances such as hair dryers are not allowed. Passengers should report dietary restrictions well before departure and plan to provide their own dinner on boarding night.

Heritage sails from 11 Front Street in Rockland, Maine. Rockland is about two hours from Portland and four hours from Boston. Cape Air provides flights from Boston, and Concord Coach offers bus service from Boston and Portland.

The sailing season generally runs from June through early October.

A Maine windjammer cruise is best suited to travelers interested in traditional sailing, maritime history, island scenery, communal meals, slow travel, and an itinerary determined by the wind.