Navigating the Coast of Maine on a Historic Windjammer

The crew declared the weather “particularly favorable,” though it felt otherwise as the ship tilted perilously close to the icy waters. As the wind whipped against my face, I pondered whether it would be safer to retreat to the galley or stay above deck if we capsized. After all, this vessel was nearly a century old—a National Historic Landmark. Could it truly withstand such fierce winds? Glancing anxiously at the helm, I spotted Captain Jocelyn Schmidt and her husband, Captain Justin Schaefer, both seemingly enjoying the thrill, barking commands while the crew dashed around the deck, tying and untying ropes, their excitement evident.

“This,” declared Susan, a fellow sailor and loyal guest for 15 years, “is an ideal sailing day.”

The J&E Riggin, our home on the water for the week, hadn't always been a passenger ship like it was for Susan and me. Built in 1927, it originally served as an oyster-dredging vessel. Designed for practicality, it was fast from the outset, winning the only Oyster Schooner Race in 1929. I would later discover just how useful its speed would be.

I found myself in coastal Rockland, Maine, about two hours north of Portland, eager to immerse myself in life aboard a windjammer. Traditionally, a “windjammer” refers to a tall-masted sailboat, often square-rigged, used for carrying cargo, typically featuring two to five masts. These ships were once a common sight in Maine, but as time marched on and modernization took hold, their numbers gradually declined.

This is the reason the Maine Windjammer Association (MWA) was established in 1977. The founding members aimed to preserve these magnificent vessels from vanishing entirely, pooling the coast’s resources along with their diverse talents and business savvy to form the largest fleet of windjammers in North America. Their collective efforts created a much greater impact.

More than 45 years after its inception, the MWA is gradually evolving. Captain Schmidt is one of two female captains in the association, and nearly half of the vessels are now owned by women. The year 2014 saw the first female mate aboard, and all-female crews are becoming more common. In recent years, the average age of the owners has decreased to 36, with almost half of the vessels now in the hands of younger captains.

Schmidt and Schaefer were once the youngest in the field, but they have witnessed a surge of peers taking over businesses and becoming “stewards of these vessels themselves,” as Schmidt noted. “Now, there are many young voices in the room. We all arrived at this point together, having grown up as green deckhands on these ships, and it's thrilling now that we are all captains.”

The 2022 season marks only the second year that Schmidt and Schaefer have owned the Riggin, yet it’s far from their initial experience on the vessel. Schaefer's journey began as a 13-year-old passenger—after that first trip, he was captivated. He returned as an apprentice, then progressed to deckhand, and ultimately became a mate. Schmidt's adventure with historic vessels started during a school excursion aboard a schooner. With her background in education and history, she cherished the ships as immersive learning spaces. As both worked on windjammers in Rockland, the couple met and fell in love aboard these very ships. Now they are the ship’s owners, yet they do not see themselves in that light.

“Technically, we own it on paper,” Schaefer stated. “But we consider ourselves caretakers; stewards maintaining it for all the people who visit year after year. It’s more about stewardship than ownership.”

A windjamming cruise demands a distinct sense of adventure. The Riggin measures only 120 feet in length, with much of the original wood preserved on the ship's underside. Eleven cabins accommodate 24 guests in close quarters, and the living arrangements are quite . . . snug. I didn’t share my cabin, but if I had to, it would need to be with a very close friend. This ship fosters a sense of familiarity: sixty percent of guests return. After completing three cruises, they earn the title and patch of “Riggin Relics.”

The Riggin Relics appeared to feel right at home, assisting to guide newcomers like myself. Indeed, some crew members were former passengers, while some passengers had once served as crew. I envied their ease in moving about the ship, contributing without being intrusive. There was also plenty of work to be done. Guests are encouraged to pitch in; their strength is essential for hand-cranking the 500-pound anchor or hoisting the 3,000 feet of sails supported by thick masts as wide as a grown man’s thigh.

The crew manning the ship was composed of young adults in their late teens and early twenties. They worked long hours with minimal breaks. Scurrying from rope to rope, they would reach high on their tiptoes and drop their body weight low into a squat. It’s well-known that sailing a ship is no easy feat; here it was fully evident in all its ruggedness.

While the crew was busy, the guests mastered the art of relaxation: playing cards and reading. When the weather turned briefly sour, we gathered around the galley’s cast-iron wood-burning stove for warmth. Our fingers warmed by steaming mugs, we savored the sweetness of powdered sugar from freshly baked Mexican cookies. Time was marked only by the ringing of the dinner bell, and by week's end, we had become like Pavlov’s dogs, eagerly lining up for delicious dishes such as fresh fish chowder, cherry-glazed pork tenderloin, and homemade maple cardamom sausage.

Out on the open sea, cell service was nearly nonexistent, and we had only two 12-volt USB outlets for power. Those of us used to constant activity were compelled to slow down and forge connections. The stunning coastline provided a captivating backdrop for deep conversations about love, loss, and life itself.

As we sailed, we spotted porpoises, seals, and countless lobster buoys along the coast of Maine. Isolated houses peeked out from islands dense with trees. Many of these islands are reachable only by private boats, and one day we docked at a secluded beach where we enjoyed a traditional lobster bake. After all, we were in Maine. Passengers were encouraged to indulge in as many soft-shelled lobsters as they desired, and I managed to devour two. With lobster juice running down our elbows, we watched the sun dip into the shimmering waters, realizing why some guests return year after year.

Nights were filled with conversation and more card games, illuminated by the soft glow of kerosene lamps. While the crew handled the ship during the day, the evenings offered a chance to unwind. We engaged in deep discussions and intense cribbage competitions in the galley. The weather was so pleasant that a few guests opted to sleep on deck under the stars.

“It’s amazing how a floating piece of wood can bring together 24 strangers from diverse backgrounds and transform them into close friends in just four to six days,” Schaefer remarked. “It creates a truly unique atmosphere. This ship becomes theirs, too.”

He was absolutely right. Each day we sailed, we grew more at ease. We had no choice! In such a compact vessel, nothing remained private. You could hear every creak of a footstep, the hushed tones of whispers, and even the soft rumble of a neighbor’s stomach through the thin walls. The gentle lapping of water against the hull provided a soothing lullaby, rocking us to sleep.

The rugged landscape of Penobscot Bay, teeming with wildlife (those lobsters, sigh), was one reason I was drawn to this place. Another was the Great Schooner Race, an exhilarating contest of wind, sails, and strategy among North America’s largest annual assembly of traditional schooners. While most days on the Riggin were about going where the wind took us, this particular day was dedicated to maximizing our wind harnessing.

Witnessing a century-old vessel being pushed to its limits is incredible—add half a dozen historic windjammers, and the scene becomes unforgettable. To top it off, the Riggin clinched first place in her class, thanks to Captain Schaefer's skilled seamanship.

Following the race, both crew and guests gathered onshore to celebrate. Throughout our journey, the camaraderie among many members of the MWA was clear. At one point, the rudder on our small yawl broke, and the captain of the Stephen Taber, another ship in the association, offered a spare part he had on board. Meanwhile, two of our passengers fashioned a makeshift rudder. At another time, when the American Eagle needed help offloading passengers, our captains stepped in to shuttle them back and forth. When the Stephen Taber ran low on water, we were prepared to share our surplus.

“We’re always bouncing ideas off each other and lending a hand,” Schaefer noted. “Sometimes when I need to dock and the wind isn’t cooperating, I can call any of those guys on the dock, and they’ll come out in their yawl boats to give me a push.”

Each vessel in the association has its own unique character. The Riggin is celebrated for its delicious food and eco-friendliness. While the primary aim of the Riggin isn’t to emphasize sustainable practices, the limited resources on a boat make that impossible to ignore. With a finite supply of food and only 800 gallons of water for a week, nothing is taken for granted. As Schmidt stated on the first night, “We have enough for everyone to use, but not to waste.”

Herbs and honey used in the kitchen came from Captain Schmidt’s garden, and compost scraps returned to nourish that same garden. A highlight of the windjamming experience is the breathtaking views and access to landscapes that remain largely untouched by human activity. As part of their commitment to preserving the coast, the Riggin and the other boats in the association are certified Leave No Trace.

The captains make an effort to instill a love for sailing in young passengers whenever they can. Part of this involves giving back, much like how the crew from Schaefer’s inaugural journey on the J&E Riggin inspired his passion for the sea. Another aspect is ensuring that the Riggin and other windjammers keep sailing. Given that the cruise demographic is predominantly older and white, it’s increasingly important to share the joy of windjamming with younger generations who can carry on the tradition of supporting these ships.

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