Sailing the Coast of Maine on a Historic Windjammer

Windjammers are century-old multi-masted sailboats that have been reborn as cruise ships run by young captains keeping history intact.

An image of an historic windjammer sailing on calm seas near Maine.

What’s it like to sail on a historic windjammer? One traveler hits the seas to find out.

Photo by Nick Parson

The weather was “particularly favorable,” according to the crew. Didn’t seem that way as the ship leaned dangerously close to the frigid Maine waters. As the wind whipped my cheeks, I debated whether it would be safer to hide in the galley or stay up top if we capsized. After all, this was a nearly 100-year-old vessel. A National Historic Landmark. Could it really handle these intense winds? Peering anxiously at the helm, I saw Captain Jocelyn Schmidt and her husband, Captain Justin Schaefer. They seemed to be relishing the experience, shouting commands. The crew rushed back and forth on the deck, tying and untying ropes, their adrenaline palpable.

“This,” said Susan, a fellow sailor and longtime guest of 15 years, “is a perfect sailing day.”

The J&E Riggin, our floating home for the week, hadn’t always been carrying passengers like Susan and me. She was built to be an oyster-dredging vessel in 1927. Although designed for utility, the ship was quick from the start, winning the only Oyster Schooner Race in 1929. Her speed would come in handy, I would later find out.

I was in coastal Rockland, Maine, about two hours north of Portland, to experience life on a windjammer. Historically, a “windjammer” is simply another word for a tall-masted sailboat, often square-rigged and used to carry cargo, with anywhere from two to five masts. These ships were once a common sight in Maine, but with time and modernization, their numbers slowly dwindled.

This is why the Maine Windjammer Association (MWA) was founded in 1977. The original founders wanted to ensure that the beautiful vessels didn’t disappear completely, so they harnessed the coast’s riches, their individual strengths, and business acumen to create the largest fleet of windjammers in North America. Together, their reach was much more substantial.

More than 45 years since the MWA was first founded, the face of the association is slowly changing. Captain Schmidt is one of the two female captains in the association, and nearly half of the vessels are owned by women. While 2014 marked the first time a female mate was on board, all-female crews are no longer unheard of. In the past few years, the median age of the owners has dropped to 36; nearly half of the vessels have come under the ownership of younger captains.

J&E Riggin, a historic windjammer in Maine, races in the Great Schooner Race in 2022.

The “J&E Riggin” midway through Maine’s Great Schooner Race.

Photo by Nick Parson

Schmidt and Schaefer were once the youngest, though they’ve seen a flurry of peers take over businesses and become “stewards of these vessels themselves,” said Schmidt. “Now there are a lot of young voices in that room. We all are coming in at the same time, and we all came up together on these ships. So we work well together, we collaborate well together, because we were all little green deckhands together, and it’s really exciting now to all be captains.”

The 2022 season is only the second that Schmidt and Schaefer have owned the Riggin, but it’s hardly their first time on the vessel. Schaefer’s relationship with the Riggin began as a 13-year-old passenger—after that first trip, he was hooked. He returned first as an apprentice, then as a deckhand, and finally as a mate. Schmidt began her journey with the historic vessels during a school trip traveling on a schooner. With a background in education and history, she loved the ships as a learning environment. With both of them working on windjammers in Rockland, the couple soon met and fell in love while working on the ships. Now, they own the ship but don’t view themselves as owners.

“On paper, technically, we own it,” said Schaefer. “But we’re just caretakers; we’re just stewards keeping it going for all the people that come year after year. It’s more of stewardship than ownership.”

A windjamming cruise requires a unique sense of adventure. The Riggin only spans 120 feet in length, with much of the original wood intact on the bottom of the ship. Eleven cabins housed 24 guests in close quarters, and the accommodations are . . . cozy. I didn’t have a roommate, but if I were bunking with someone else, it would have to be a very close friend. On this ship, there’s a built-in familiarity: Sixty percent of guests are return visitors. Complete three cruises and they’re awarded the title and patch of “Riggin Relics.”

The Riggin Relics seemed comfortable and at home here, helping to guide new guests like me. In fact, some crew members are former passengers, and some passengers are former crew members. I envied how they moved about the ship, pitching in to help without being in the way. There was also plenty of work to do. Guests are encouraged to take part; their strength is integral to hand-cranking the 500-pound anchor or raising the 3,000 feet of sails supported by thick poles the width of a grown man’s thigh.

The crew operating the ship was in its late teens and early twenties. They worked long hours with short breaks. Rushing from rope to rope, they’d reach up on their tiptoes and throw their body weight down low into a squat. It’s no secret that sailing a ship is challenging; here it was on full display in all its grit.

It’s really cool how a floating piece of wood can do that—take 24 strangers from all walks of life and within four to six days have people from strangers to best friends.
Justin Schaefer

While they worked, the guests perfected the art of relaxing: playing cards, reading. When the weather turned sour, which only happened briefly during our trip, some of us sought warmth from the galley’s cast-iron wood-burning stove. Our fingertips were warmed by hot mugs, and our lips dusted with powdered sugar from freshly made Mexican cookies. Time was distinguishable only by the food served with the ring of a bell. By the end of the week, we’d become Pavlov dogs for that bell, eagerly lining up for dishes like fresh fish chowder, cherry-glazed pork tenderloin, and homemade maple cardamom sausage.

As you might expect out on the open sea, cell service was nearly nonexistent, and our electricity was limited to two 12-volt USB outlets. Those of us constantly on the go were forced to slow down and even form connections. The coast was a compelling backdrop for conversations of surprising depth, about love, loss, and life.

As we sailed, we spotted porpoises, seals, and hundreds of lobster buoys along the coast of Maine. Lone houses peeped out of islands thick with trees. Many islands are only accessible by private boats, and one day we stopped on a secluded island beach. Here, we had a lobster bake. We were in Maine, after all. Passengers were encouraged to eat as many soft-shelled lobsters as they wanted. I made it through two. Lobster juice dribbling down our elbows, we watched the sun begin its descent into the mercury-like waters. At that moment, I could see how some guests made their way back year after year.

The nights were spent chatting and playing more cards by the light of the kerosene oil lamps. While the crew was busy running the ship during the day, the night was when things slowed down. Together, we had serious conversations and even more serious cribbage competitions in the galley. The weather was lovely enough that a few guests slept on the deck.

“It’s really cool how a floating piece of wood can do that—take 24 strangers from all walks of life and within four to six days have people from strangers to best friends,” said Schaefer. “That is a pretty special environment. It becomes their ship, too.”

He was right. As we sailed each day, we got more comfortable. We had to! On such a small ship, nothing is a secret. You could hear the creak of a footstep, the deep tones of whispers, and even the low growl of a neighbor’s stomach through the walls. You could also hear the soft lapping of the water against the ship’s hull, creating a gentle lullaby as the waves rocked us to sleep.

The rocky terrain of Penobscot Bay, along with its bountiful wildlife (those lobsters, groan), was one of the reasons I was drawn here. Another reason was the Great Schooner Race, an epic battle of wind, sails, and strategy among North America’s largest annual gathering of traditional schooners. While most days on the Riggin were about seeing where the wind takes you, this one day was about harnessing the wind to its maximum potential.

It’s incredible to watch a century-old vessel being pushed to its limits—multiply that by half a dozen historic windjammers, and the image was worthy of permanence. Best of all, the Riggin won first place in her class thanks to the seamanship of Captain Schaefer.

Maine lobsters spill out of a bucket on a beach.

After a big race, what better way to celebrate than with lobster?

Photo by Sean Sheppard

After the race, the crew and guests all gathered on land to celebrate. Throughout our trip, the kinship felt among many in the MWA was evident. At one point, the rudder on our small yawl boat broke. The captain from the Stephen Taber, another ship in the association, offered an extra he had on board. In the meantime, two of our passengers stepped in to create a makeshift rudder. The American Eagle, another schooner in the association, needed assistance offloading passengers at one point, and our captains shuttled them back and forth. At another time, the Stephen Taber was running low on water, and we were ready to offer our excess.

“We’re always constantly bouncing ideas off each other and helping each other out,” said Schaefer. “There are times when I have to come into the dock, and the wind is super unfavorable. I can call up any of those guys on the dock, and they’ll come out in their yawl boats and give me a push.”

Each vessel in the association has a different personality. The Riggin is known for its food and ecofriendliness. While the main focus of the Riggin isn’t to remind you of sustainability practices, there’s no way to avoid the finite state of resources on a boat. You don’t take anything for granted with a set amount of food and 800 gallons of water for a week-long journey. As Schmidt said on the first night, “We have enough for everyone to use, not to waste.”

Herbs and honey in the kitchen came from Captain Schmidt’s garden, and composted scraps would return to that same garden. A feature of the windjamming experience is the view of and access to scenic landscapes that haven’t been heavily impacted by human extraction. As part of their commitment to protecting the coast, the Riggin, along with the association’s other boats, is certified Leave No Trace.

When they have the opportunity, the captains try to nurture that love in other young passengers. In part, that involves paying it forward, as the crew from Schaefer’s first trip on the J&E Riggin helped foster his love for sailing. Another part is ensuring that the Riggin and the other windjammers continue to sail. Because the general demographic of the cruises leans heavily toward white seniors, there is an added urgency to passing on the appeal of windjamming to younger generations who can continue to support the ships.

“You’ve got to keep that spark alive,” said Schaefer. “That’s the only way to keep these ships alive.”

Iona Brannon is a travel writer captivated by the connection between physical space and the sense of belonging. She is still searching for her “forever home.”
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