What is it like to sail on a Maine windjammer? Find out why this outdoor adventure should be top everybody’s bucket list.

The Maine windjammer’s chef crossed the deck carrying a slice of chocolate cake. When she stopped, she said, “It’s come to my attention that someone is here celebrating a birthday.” Everyone knew who she meant. Throughout the four-day cruise, we had all heard how Wanda had booked the cruise to commemorate her 70th birthday. At this point, just a few hours before pulling back into port in Camden, Maine, I knew almost everyone’s story, from the 21 passengers to Captain Barry King and his crew.

“We should sing happy birthday,” someone said, and we did. Then, as Wanda took her first bite, we headed to the galley for our slice.

Our journey aboard the Schooner Mary Day may have lasted only a few days, but we quickly became a community. Some of them were sailing enthusiasts; others had never sailed before. Either way, we all had a chance to set aside our phones and focus on each other and the scenic coast. Sailing on Maine windjammer is a bucket list adventure.

The ship’s wheel on board the Schooner Mary Day. Photo by Teresa Bitler

Maine Windjammer Cruises

A windjammer, or schooner, is a merchant sailing vessel with multiple masts. The nine schooners in the Maine Windjammer Association’s fleet range from 64 to 132 feet on deck and are based in Rockland or Camden. They can carry 16 to 40 guests and four to 10 crew members. Cruises range from 3 to 6 days, with up to 9-day cruises available on some schooners.

Each cruise is themed—I was on the lighthouse cruise with an expert who shared coastal history and pointed out the historic structures we passed—and features an all-you-can-eat lobster bake. Are you not keen on the theme or a fan of lobsters? No worries. You can lounge on the deck or help the crew hoist sails, navigate, or take a turn at the wheel. As for the lobster, you’ll have plenty of options at every meal.

Every cruise features a lobster dinner. Photo by Teresa Bitler

I sailed aboard the Schooner Mary Day, named for the original captain’s wife, in early June 2021. Although it launched in 1962, the Mary Day is reminiscent of schooners that would have sailed the Maine Coast more than 100 years ago. You truly do feel like you’ve stepped back in time.

Getting Ready for the Maine Windjammer Journey

Like many out-of-state passengers, my mom and I flew into Portland International Jetport—you can also fly into Bangor International Airport—and took a limo service to Camden, about two hours north. If I had to do it over again, I would have rented a car and spent a few days before or after exploring Maine. That’s an adventure for another day.

The harbor at Camden, Maine. Photo by Teresa Bitler

When we arrived, we missed the orientation and the cheese board teeming with cheeses, local honey, and fresh berries. The crew brought our luggage to our room, which was a bit of a shock. Steep stairs led down to a tiny compartment with doors leading to six rooms. Ours consisted of three staggered bunks and was so small only one of us could stand inside it at a time. I wasn’t quite sure how we would manage the next four nights.

After lobster rolls at Peter Ott’s on the Water, we had a chance to find out. And, you know what? It was fine. My mom got ready for bed first. Then, I came down. We had a small sink in our room to wash up and brush our teeth and plenty of space to store our gear on the extra bunk and under our beds. The room size wasn’t an issue since we were barely in our room except to sleep.

Lanterns light the ship at night. Photo by Teresa Bitler

Setting Sail on a Maine Windjammer

Quiet hours on Mary Day are from 11 p.m. until 7 a.m. when coffee is served. I was up well before then. Breakfast on the first day was my favorite of the trip: French toast with blueberry compote, sausage links, and fresh fruit. After that, I watched the Lewis R. French, the Angelique, and two other schooners head out into Penobscot Bay. We left last.

I’m not sure what to expect, but I took a dose of Dramamine before breakfast, even though most people don’t get sick. My mom did, too. And I was glad I did. The morning had grown overcast, and the water was a little choppy when we entered the bay. Despite that, I felt fine. My mom didn’t even take Dramamine for the rest of the trip. I only did one 24-hour, non-drowsy dose once a day because I didn’t want to chance it.

Lighthouse on the Maine coast. Photo by Teresa Bitler

The weather hampered things a bit that first day. It was cold and windy. We could barely see the coast at times because of the clouds. And then the rain started. It wasn’t hard, but it was enough that my mom and I retreated to our cabin to read. I fell asleep.

When I woke, the Mary Day had stopped. I climbed up on deck to see nearly the entire fleet anchored in a cove off the Fox Island Thorofare between North Haven and Vinalhaven.

The Gam and Lobster Bake

On the season’s first cruise, the fleet’s ships gather for games and festivities late in the afternoon. Known as a gam, the event started with a boat rowing from ship to ship to deliver grog for the passengers. Ours came just as the bins of live lobsters were hauled on deck. (Typically, the lobster bake would have been held onshore, but perhaps because of the rain, the captain decided to do it onboard.)

Schooners at the gam. Photos by Teresa Bitler

Next, each ship sent a team in a small vessel to race from one ship to another, collecting tokens. Our team came in second. As the sun set, we savored lobsters, hamburgers, and hot dogs on deck. A band in a small boat floated from ship to ship, performing sea songs. With dinner over, we sipped grog and watched the lights from the other schooners nearby bob on the horizon.

Continuing the Windjammer Journey

The following day, I woke early to catch the sunrise but found a thick fog. As we ate breakfast, the other ships began pulling anchors and setting sail one by one. Our captain opted to wait for some fog to burn off, so I attended a lecture on lighthouses. By the time it was over, the other ships were gone. We pulled up anchor and got underway.

Two schooners in the mist. Photo by Teresa Bitler

Eventually, the fog gave way to partly a cloudy sky. About mid-afternoon, we stopped at Holbrook Island State Park and had the option to explore for about an hour. This is a good place to note that a windjammer cruise has no set itinerary. You sail where the wind takes you; this day, after our state park sojourn, it brought us to Castine. We had a few hours of sunlight to explore, but unfortunately, the few shops in town had already closed.

The crew at work. Photo by Teresa Bitler

We spent most of the next day sailing. The weather, for once, was perfect. One of the passengers, a photographer, held an informal class for anyone interested while others staked out a spot to read or watch the shoreline. After we dropped anchor for the night, a few passengers braved the chilly waters and jumped off the ship’s side for a swim. It would be our last night on the ship, and I was not looking forward to saying goodbye.

Disconnect on a Maine Windjammer

King, who owns Mary Day and captains it, says everyone who boards comes from a different place in life. You don’t know what they’ve been through or what they’re hoping to get out of the experience. However, he hopes it’s a chance for them to put aside their laptops and cell phones and relax.

“I hope people get a breath of fresh air,” he says. “I want them to unplug, to chill.”

The Lewis R. French. Photo by Teresa Bitler

He adds that he likes the six-day cruises the best because it takes people about three days to unwind. I would agree. I was finally getting into the sailing routine by the end of that third day. As we ate our chocolate cake on the fourth day, I wished I was on that six-day cruise.

A Word About the Food

I’m always fascinated by local cuisine, but what happens in a windjammer kitchen is nothing short of a miracle. Everything is prepared in a wood-fired oven or on its stovetop. There’s no electrical equipment—no stand mixer or blender—everything is made by hand. And, you have to deal with the tilt when the ship turns.

French toast with blueberry compote. Photo by Teresa Bitler

“Everything shifts to one side, and you have to keep on working,” says Tiffany Cole, a Le Cordon Bleu-trained chef who joined the Mary Day this year after cooking for Cirque du Soleil.

Meal after meal, she and the other chefs aboard the Maine Windjammer Association’s schooners serve gourmet dishes despite cramped conditions and having to dig for ingredients under galley floors and seat cushions. During our four-day cruise, we had New Orleans-style gumbo, seafood chowder, cinnamon pecan biscuits, and shakshuka, an egg dish simmered in tomatoes, onions, and peppers.

Relaxing on the Schooner Mary Day. Photo by Teresa Bitler

Oh, and that chocolate cake? It wasn’t just any cake, of course—it was layered with rich cream and covered in chocolate ganache. Because why not?

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More About Maine Windjammers

The fleet’s schooners sail from late May to mid-October. Prices for this all-inclusive adventure with Maine Windjammers begin at $675 per person. Keep in mind there is no set itinerary. You go where the captain and the wind take you.

The Schooner Mary Day. Photo by Teresa Bitler

Speaking of which, each captain owns his own ship, and each ship has its own unique story. Experiences on board each vessel vary. Visit sailmainecoast.com to learn more about the ships and see which might be right for you. If you’re undecided, though, I highly recommend the Mary Day. Be sure to check out Wander for more to see and do during your visit to Maine.