The whistling chirp of the wharf's resident osprey greeted me as I walked down the gangway toward Ladona. The reflection of the ship's pristine, cream-colored hull rippled on the water's dark surface. Late afternoon sun spilled golden pools onto the deck. Everything gleamed — the polished cast-brass wheel, the long mahogany deck table, the massive Douglas fir bowsprit, the gilded letters engraved on the bow. I had seen photographs of the ship during the darkest days of its restoration. The result was nothing short of miraculous.
It was late September, and I'd come to Maine for a five-night adventure on board Ladona, one of nine traditionally rigged sailing vessels that make up the Maine Windjammer Association, the largest fleet of historic ships in North America. From home ports in Rockland and Camden, the MWA fleet travels a 100-mile swath of coast between Boothbay Harbor and Bar Harbor, each schooner carrying between 17 and 40 guests. The region has more than 2,000 rocky, windswept islands off its jagged coastline. Lighthouses perch on rugged outcrops while hidden coves and snug fishing ports provide peaceful overnight anchorages.
My first foray into windjamming in Maine was back in 2015, when I took a knitting-themed cruise with two of my daughters, then eight and 10. Over the course of four days my girls and I perfected our stockinette stitch in between raising sails, beachcombing along rocky shorelines, and scanning the Atlantic for porpoises and harbor seals. Two years later I took a trip with my husband on Victory Chimes, one of the last surviving three-masted schooners in the United States; its likeness adorns the back of the Maine state quarter.
By that time, I'd fallen hard for these beautiful old boats — for the way they had evolved into such a natural part of Maine's coastal aesthetic, for the maritime heritage they kept alive, and for the quiet magic that occurred when they harnessed the wind and skimmed over the ocean. Yet my experiences thus far had bordered on rustic — windjamming is sometimes referred to as "camping at sea."
That evening, as dusk streaked the horizon in dusty pastels, I dove off the side. The cold seized my breath at first, but I felt its rhythm return as I began to swim, mesmerized by the spectacle of sail that surrounded me.
Then, I heard about Ladona, which had undergone an extensive rebuild with the goal of making windjamming a more polished experience. Intrigued, I set sail last fall, opting to join a trip that included a gathering of the entire Maine windjammer fleet in Brooklin Harbor, home of the legendary WoodenBoat magazine and boatbuilding school.
Ladona began its life a century ago as the beloved family yacht of American industrialist Homer Loring. Designed by celebrated naval architect William H. Hand Jr., the boat, with its graceful profile and billowing sails, finished first in class in the 1923 Bermuda Cup. In later years, Ladona patrolled for German subs out of New York Harbor during World War II and worked as a fishing dragger in Stonington, Connecticut, before being refitted as a training vessel named for Nathaniel Bowditch, the father of modern maritime navigation. In 1976, the Bowditch joined Maine's windjammer fleet as a passenger schooner, sailing for nearly four decades — until financial woes landed it on the auction block in February 2014.
The night before I set sail, I met two of Ladona's co-owners, captains Noah Barnes and J. R. Braugh, for a lively dinner at Primo, chef Melissa Kelly's farm-to-table restaurant in Rockland. Over cocktails and a dozen sublimely fresh wild Maine oysters, the two shared the story of how they, along with Noah's wife, Jane Barrett Barnes, came to take ownership of Ladona, a boat that Noah had long coveted.
"I'd had a crush on the Bowditch since I was about eight," said Noah, who grew up running sailing trips with his parents on board the schooner Stephen Taber and left a career in New York City to take over the helm when his parents retired in 2003. "If you had asked me back then if there was any other boat besides the Taber that I would have loved to have had, I would have said the Bowditch."
Related: 20 Classic Summer Vacations Everyone Should Take at Least Once
After the auction, which attracted no bids, the Bowditch was towed to Rockland, where it languished, mastless, for months. "Seeing such a fine vessel sitting at our dock not getting any better — it just broke my heart," Noah recalled. In early 2014, after finally persuading Jane that buying the Bowditch was a semi-sound idea, Noah made his friend J. R. an offer he hoped he couldn't refuse. For J. R., a West Coast transplant and longtime schooner captain who had come to Maine 15 years earlier to work on the windjammers, the chance to become part owner of the historic ship and help return it to its former glory was irresistible.
Demolition began the following September, and over the course of 18 months, which included one of the toughest Maine winters anyone could remember, the captains worked with a team of local shipwrights and carpenters to complete a 90 percent rebuild of the ship. Today, it shines again, rechristened Ladona and ready to sail into the future.
On board I met first mate Sabrina Craig, who had recently earned her 100-ton Master Captain's license; second mate Kelsey Nevill, otherwise known as Noodle; and galley hand Colleen McNulty, or Pip. Noodle led me below to a cozy single berth near the ship's fore. While the Bowditch could accommodate 24 passengers, Ladona's owners scaled that back to 17, reconfiguring the space to carry fewer guests in greater comfort. Although the boat's nine light-filled staterooms are still snug, bespoke touches — handsome brass hardware, plush robes, soft linens, and mirrored vanities set with hammered-copper sinks — add a sense of vintage elegance.
I followed the aroma of baking bread to the galley, where chef Anna Miller was removing a tray of baguettes from the oven. Bundles of leafy greens, a mound of romano beans, and bouquets of fragrant herbs lay on the wooden countertops. Colleen wrapped the produce in tea towels and packed the bundles into benches that cleverly doubled as coolers.
More Trip Ideas: The Best Small Coastal Towns in New England
Jane and Noah wanted sailing on Ladona to feel like a dinner party that lasted a week. Whereas Noah's mother made turkey dinners and sherbet punch on the Taber back in 1983, guests are now served Chef Anna's duck confit and wines hand-selected by Jane, who worked in sales for Veuve Clicquot before helping Joe Bastianich launch his family's wines.
I woke early the next morning to the slap of salt water hitting the deck as the crew went about their chores. Colleen had laid the table with a platter of buttery cranberry scones and hot coffee from Rockland's Rock City Coffee. The scent of frying bacon wafted up from the galley, where Anna turned out blueberry pancakes and plump, made-to-order omelettes. Camping this was not.
Before long, Ladona's lines were cast off, and the boat pushed into Rockland Harbor. On a schooner many hands do, in fact, make light work, and Sabrina asked for help raising the mainsail. Hand over hand we pulled, and the massive sail slid skyward. As it inched toward the top of the mast, crew members put their full body weight into the halyards, shouting "two, six, heave!" — an old navy chant sailors use to coordinate their efforts. Soon, all four sails caught the wind. I could tell it made a majestic sight gliding past the Rockland Breakwater Lighthouse when people waved back from the shore.
In the late 1800s, schooners plied Maine's coast by the thousands, carrying coal, granite, lime, and lumber — the building blocks of America's cities. By the late 1920s, steamships, railroads, and trucks had taken over the trade routes, rendering schooners obsolete. But in 1936 an enterprising captain named Frank Swift began offering rugged adventures aboard a converted two-masted cargo schooner, introducing urbanites from Boston and New York to the romance of the sea. The idea, according to Swift, was "not to follow an exact itinerary, but to use the winds and tides to make the cruise most interesting." Today, many of the traditions from Swift's days remain — albeit with far greater comforts — and the winds and tides continue to determine a windjammer's course.
That morning we set sail for Brooklin. I spent the day lounging in the sun with my notebook and chatting with some of the other passengers as Ladona breezed beneath a cloudless sky. A woman named Marcia said that she and her husband, Jim, had sailed on the ship before. This time, they planned to stay on board not just for this trip but for the one after it, too. They loved the easy rhythm of days spent on the ocean.
It was late afternoon when we coasted under the Deer Isle Bridge into Eggemoggin Reach on our final approach into Brooklin for the WoodenBoat rendezvous. Most of the fleet had already arrived, and J. R. named each ship we passed — the Heritage, the J. & E. Riggin, the Mary Day — as Ladona slid up alongside the Stephen Taber. Noodle threw our lines across to Noah, and the two crews went to work lashing the boats together for a schooner gam—a 19th-century tradition that gave crews on those old cargo schooners a way to pass the time in good company while waiting for the wind to arrive. Tonight it allowed us guests to mingle between the two ships, sharing stories of our day at sea.
"At the end of the day, there's just something intrinsically good and emotionally satisfying about a wooden boat."
Fleet gatherings happen a handful of times each season, but the annual assembly at WoodenBoat felt especially meaningful. In 1974, a young boatbuilder named Jon Wilson had the idea to start a magazine dedicated to wooden-boat craft and heritage. As fiberglass boats began gaining a foothold in the industry, Wilson noticed that classic wooden vessels were being relegated to the corners of shipyards. His goal was to slow down their extinction. The magazine, which began in a tiny off-the-grid cabin in the woods, moved to a 60-acre waterfront property, launched a boatbuilding school, and amassed more than 100,000 readers in the span of a decade. Today, the Brooklin campus is a site of pilgrimage for aficionados from around the world.
As we entered the harbor, it felt as if the entire place thrummed with energy. Small craft zipped between the windjammers. Some belonged to WoodenBoat's sailing school. Others, yawls and rowboats belonging to the schooners, ferried passengers ashore to explore. I crossed over to the Taber just as Noah was stepping back from a small brass naval cannon on the deck, its muzzle pointing toward the sea. "Fire in the hole!" he shouted. Sparks flew from the fuse; seconds later a mighty boom ricocheted through Brooklin Harbor. The cannon fire was pure pageantry — a nod to maritime tradition and a nostalgic way to salute the final fleet gathering of the season. All around the cove, tall ships rested at anchor, mainsails raised majestically to catch the last rays of the September sun.
That evening, as dusk streaked the horizon in dusty pastels, I dove off the side of the Taber. The cold seized my breath at first, but I felt its rhythm return as I began to swim, mesmerized by the spectacle of sail that surrounded me. Afterward, I sat bundled in layers on Ladona's deck and watched the stars congregate above the masts. "At the end of the day," Noah had said earlier, "there's just something intrinsically good and emotionally satisfying about a wooden boat." At that moment, I couldn't have agreed more.
In the morning I emerged from the cocoon-like warmth of my cabin and saw that a moody sky had settled over the harbor. "In Maine, there are strong breezes and then there are strong breezes," said J. R., who was clad in orange waterproof overalls. "And I think today's gonna be borderline." The crews detached Ladona from the Taber and we raised the sails, which heaved the boat full tilt into Jericho Bay. The water was steel gray and churning with whitecaps. The bow collided with a particularly big wave and a rush of surf spilled over the deck.
The wind eased as we sailed past Bass Harbor Head Lighthouse on the southern tip of Mount Desert Island. "We really got her up to a gallop, didn't we?" J. R. said with a chuckle. He steered into Somes Sound, a long inlet that gives the island the shape of a lobster claw. The sun made a brief appearance, and a passenger named Skip remarked that in Maine, you experience all four seasons in a day. A bald eagle, gripping a fish, flew overhead and disappeared into the branches of an enormous spruce. To our port side, Man of War Brook Falls spilled into the sound from Acadia Mountain. J. R. told us that 19th-century ships used to replenish their water stores from it.
We dropped anchor in Somes Harbor. A guest from Florida took the paddleboard for a spin while another tried his luck with a fishing rod. I went ashore and spent a mellow hour stretching my legs in the tiny village of Somesville, Mount Desert's earliest settlement, photographing the town's arched footbridge and hiking around the rocky harbor. At sunset, we gathered for dinner beneath Ladona's canopy, which glowed with light from a string of paper lanterns. Skip took out his guitar and as we sang along to all of the requisite folk songs, I felt our trip settling into a groove.
Life on the Maine coast sharpens into focus when traveling by schooner. The windjammers share their sailing grounds with lobstermen, fishermen, oyster growers, scallop divers, and seaweed farmers — folks whose backbreaking work in these waters sustains the coastal communities. One afternoon we sailed into Stonington, once a boomtown that attracted thousands of immigrants in the late 19th century to work in granite quarries. Today, Stonington's fleet of lobster boats consistently lands more of Maine's famed crustacean than any other port in the state.
Walking along Main Street, I passed salt-grayed cedar houses and wooden tubs that spilled over with late-summer blooms. Vibrant canvases on the lawn of a white clapboard house caught my eye. Inside, I lost myself among a kaleidoscope of landscapes by artist Jill Hoy, many of which captured the essence of coastal Maine. Back on board, I found lunch in full swing. I helped myself to Anna's famous tortilla pie. Sabrina and Noodle raised the anchor, and J. R. steered Ladona out into the bay.
Related: Sailing Around Greece in the Fall Offers a Second Chance at Summer
Throughout the trip, J. R. regaled us with colorful tales of Maine's historic harbors and working waterfronts. Stories about a centuries-old osprey nest that sits atop Pulpit Rock near the island of North Haven. About the astronomical investment of owning a windjammer and the compromises made by the captains who act as their stewards. About a local character folks called John the Diver — boaters radioed him when they accidentally got their propellers tangled in lobster buoy lines, something the lobstermen didn't much appreciate.
Thousands of those buoys stud the surface, each one painted in a distinct color and pattern chosen by the operation that owns the traps. J. R. was careful to avoid them, explaining that there can sometimes be animosity between schooner operators and lobster harvesters. "They don't always differentiate us from a typical, snooty yacht and they worry that we're going to foul their gear," he said. "But when I tell them that I always steer clear of the traps, they realize I'm on their team."
Procuring lobsters for Ladona's traditional picnic is another way J. R. has strengthened those ties. "Anytime you buy directly from them, it's a win-win," he told me one afternoon. He'd gone off earlier in the skiff with a wad of cash and a large crate and returned later with the goods — about three dozen live lobsters, just plucked from the sea. Later that day we dropped anchor in an idyllic cove off Marshall Island, an uninhabited preserve protected by the Maine Coast Heritage Trust.
As J. R. ferried guests and crew ashore, I watched from Ladona's paddleboard, stirring the water's obsidian surface into little whirlpools as I slid across the cove. Sabrina had started a fire on the island's rocky beach, and Noodle set a big galvanized tub of seawater on the hot coals. Soon they'd fill that tub with lobsters, topping them with a heaping pile of seaweed to lock in the steam, and then we'd all gorge ourselves on the sweet, succulent meat, dipped in drawn butter and washed down with an effervescent vinho verde appropriately named Lagosta — "lobster" in Portuguese.
But for now, I drank in the scene from afar, breathing in the salt air while trying to work up the courage to step off the paddleboard and into the water one more time. I thought back to my dinner with Noah and J. R. at Primo. We'd been talking about the huge leap of faith they'd taken with Ladona. Windjamming was an industry they wholeheartedly believed in, yet taking on the boat's restoration had required a commitment to its future. "When you're sailing on a schooner in Maine, there's five kinds of right about that," Noah had said.
On shore, the flames from Sabrina's bonfire licked toward the sky as folks helped themselves to wine. Behind me, Ladona floated in a frame of pine trees, the shape of its hull restored to its original 1920s glory, sails unfurled and gleaming. Five kinds of right, I thought. I held my breath and jumped.
The Schooner Ladona offers three-night sailings from $1,108.
A version of this story first appeared in the June 2022 issue of Travel + Leisure under the headline Plain Sailing.