Chronological / Cruises / Destinations / Maine / United States

Sailing the High Seas Aboard the Majestic Schooner Heritage

The wind roars through the sails and the sea sweeps the decks and all would-be mariners get the thrill of a lifetime racing the waves in the open ocean. For a truly unique vacation that the entire family will enjoy, try a tall ship adventure.

mainsail, Schooner Heritage

Boarding any great sailing ship is like taking a giant step back in time. Life’s tempo changes the moment you set foot on the weathered deck and hear the sheets lightly tapping high in the rigging.

Hot coffee in the morning as the Heritage gets underway

Hot coffee in the morning as the Heritage gets underway

Serenity replaces stress as you listen to the quiet creaking of the wooden giant, quiescent in a slightly undulating sea, but hoist the sails up the masts and point her into the wind, and that serenity becomes instant exhilaration as the mighty ship moves forward and the bow begins to plunge into the oncoming ocean.

The idea for our trip started at a breakfast discussion with friends. We all agreed that taking a holiday aboard a cruising schooner would be great fun. We had heard of the Maine Windjammer Association and found their website at

Schooner Heritage

After some investigation, we decided a one-week cruise on the “Heritage,” one of the ships in the Windjammer Association’s 10-schooner fleet, would make a perfect holiday.

Cozy Bunks, Schooner Heritage

Cozy Bunks

The Captains Doug and Linda Lee, Schooner Heritage

The Captains Doug and Linda Lee

Clowning with Captain Doug, Schooner Heritage

Clowning with Captain Doug

Charting a course aboard the Heritage

Charting a course aboard the Heritage

A few weeks later, we flew to Portland, Maine and hired a car for the two-hour drive to Rockland, the home port for the Heritage. We arrived on Sunday evening, just in time to go aboard. Ready for our six-day sea adventure, we grabbed our gear and carefully walked down the aluminum gangway to the waiting schooner. Captain Doug greeted us and told us where to stow our gear.

Accommodations aboard a cruising schooner

The Heritage has space for 30 passengers and ample crew. She is an authentic coastal schooner built with the passenger, rather than cargo, in mind.

Captain Doug oriented the entire complement of guests on the ship’s safety features, the location of the three passenger heads (toilets), the site of the ship’s single shower room and cozy galley/dining room, with its wood-burning stove.

An interview with the two captains

The Heritage is the brainchild of the two captains, Doug Lee and Linda Lee. Already seasoned masters while in their 20s, the young seagoing couple decided to build their own large cruising schooner from the keel up. It took one year to plan and four years to construct their dream.

Launched with significant fanfare on April 16, 1983, at the historic North End Shipyard in Rockland, Maine, the 95-foot, 165-ton Heritage is now the second largest coastal schooner in the Maine Windjammer Fleet.

The Lees have been sailing the coast of New England for over 30 years. They are a virtual treasure store of nautical history and marine lore. They are “sailing legends,” and with their heavy accents, never fail to entertain their guests with whimsical New England jokes and interesting sea stories.

More about the Heritage

Small round skylights installed in the main deck floor just above each guest cabin provide light in the daytime. There are small electric lights for night reading. Converters are available for charging shavers, digital cameras and the like.

Several cabins have bunk beds, others a small double bed. Two cabins have private toilet facilities.

There is enough head room to stand upright in all the guest quarters, and each cabin has a small hot and cold water sink. There are no TVs aboard, so it is a good idea to pack a good book or two.

A roving, a roving and a roving we will go

Guests Helping with mainsail, Schooner Heritage

We sailed with the tide early Monday morning. To get into the spirit of the voyage, the passengers are encouraged to participate in the first hoisting of the mains’l. Rope in hand, the crew leads in the traditional pulling chanty, “…way haul away, way haul away together, way haul away, way haul away, Joe.” It’s a very big mainsail, and before long everyone has caught on to the rhythm, and is heaving-ho and singing the melodic refrain as the huge gaff works its way up the mast.

Sailing the islands of Maine
Schooner Heritage

Eager to explore a deserted island

Most weekly cruises cover approximately 125 nautical miles, and all sailing is done in daylight hours.

rocky shoreline

There are some 3,000 rocky islands off the coast of Maine, and each night the ship is comfortably anchored in a quiet cove near some remote spruce-capped granite island or in a charming harbor near a seaside village or town.


There are photo opportunities at every turn of the helm. The islands are rich in color, and the sunsets are spectacular. Lighthouses glisten, and great birds and sea creatures are visible throughout the day.

All hail the queen

We were fortunate to book passage for the week that Maine celebrated its “Windjammer Days” in Boothbay Harbor. Several hundred small boats jammed the harbor as their occupants came to marvel over the beauty of the many tall ships participating in the annual festivities.

Heritage sails into Boothbay Harbor

Heritage sails into Boothbay Harbor

The Heritage, moving into the congested port under billowing sails, was the grand guest and the high point of the final day. Ship’s horns and blaring whistles welcomed her like royalty.

Windjammer Days at Bootbay

As the colossal Heritage came to rest, the crowd roared its approval and appreciation of the captain’s amazing display of seamanship in piloting the mighty ship to her place of honor.

A unique vacation

A windjammer cruise is much akin to camping, with the addition of breathtaking sea views. “Luxury” is not in the windjamming glossary of terms. However, there is ample shelter and the food is good and plentiful. Meals are included and are greatly enhanced by homemade bread and cookies fresh from the wood burning stove.

Lobster feast presented by crew of Schooner Heritage

Lobster feast presented by crew

The gastronomical highlight of every cruise is the “lobster bake.” This is an all-you-can-eat lobster and corn-on-the-cob extravaganza prepared by the crew on the beach of one of the islands.

You could get hooked

Wayne & Judy Bayliff Relaxing aboardSchooner Heritage

Doug and Linda boast that over 60% of their annual passengers are returning guests. Out of the 19 passengers on our voyage, only four of us had not previously sailed on the Heritage. Our fellow guests ranged in age from their mid-30s, to one couple in their early 80s.

Who should go?

Vacationers seeking a real-life adventure; sailors of small boats who love the tall ships and are keen to hear the howl of the wind in the gigantic sails – and ordinary landlubbers who are ready for a week full of fun and the occasional thrill of a deck awash in salty brine.

For more information look to the Heritage website at

If you go
Rockland Headlight fromSchooner Heritage

Rockland Headlight

Rockland, Maine is the home of the famous lighthouse and where you board the Heritage. It is a 78-mile drive along scenic Highway 1 from the Portland Airport.

Happy travels!

Photos © Judy Bayliff

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