I’d never had much interest in cruising, until I set sail on an old-fashioned Maine windjammer — with no itinerary

It’s the end of my first day sailing the Maine coast aboard the Angelique. Captain Dennis Gallant calls us over to the wheel if we want to know “where we are and how we got here.” That I have only a hazy idea of either is a sign that this is not a typical cruise. When sailing an old-fashioned Maine windjammer sailboat, it seems, an itinerary is just a suggestion.

Captain Dennis places a hefty wooden pointer over the nautical chart unrolled before him, indicating Carver Cove, off Vinalhaven. He traces his finger toward it, pointing out each island we’ve sailed by, from Camden Harbor into the Penobscot Bay.

A glimpse of a sea chart has always inspired a sense of possibility in me, but it’s even more thrilling now: After a year of life dictated by the pandemic, it feels revelatory to place my trust in a stranger and the power of the elements.

The only certainty about this trip was that I’d board in Camden on Sunday and return on Saturday. Where the boat would take me in between was dependent upon wind and tides, and the captain’s fancies.

The following nights’ anchorages would be in the snug harbours of quiet fishing villages or off deserted islands, but we are not alone for our night in Carver Cove. Tonight coincides with the annual “Gam,” a gathering of all nine boats that make up the Maine Windjammer Association (MWA), North America’s largest fleet of historic sailing vessels. Every summer they explore the waters of Maine, and some of the 3,000-plus islands, on small-group cruises.

The Gam — location always unknown until the day of the event — marks the start of sailing season in June, and in a typical year the boats all tie up so passengers can walk on each. But this atypical year is MWA’s first season since the pandemic started, so in lieu of large gatherings, we take to rowboats to get a closer look at the rest of the fleet.

It’s a rare, organized activity in an otherwise unstructured trip. Each day, as we sail to a destination unknown, only 19 passengers altogether, we can do as we please. I spend most of my time sitting on deck as Maine’s coastal scenery slowly slips past. The lighthouses, stockier than the willowy ones I’d grown up around in Scotland, glisten white on the sharp edges of angular coastline. There’s almost always an island in sight, most thickly forested with pine; some with just a scattering of trees rising above giant slabs of rock.

Mansions owned by summer people, and more modest year-round residences, peek through clearings. Now and again, an osprey or bald eagle flies overhead and a seal pokes its head above water. Everywhere we go, lobster buoys, resembling colourful lollipops, lie scattered over the water’s surface.

Each day we row ashore to islands and coastal villages where we’re free to explore. It’s tight quarters on board, so I appreciate the few hours of solitude as I walk along empty coastal trails, watch fishermen as they come into harbour with a day’s catch, and wander along quiet roads where the few passing drivers all wave hello.

Many of my fellow travellers have sailed the Angelique before — one couple are on their 10th cruise. Most are keen sailors and jump up as soon as the three-woman deck crew calls out for help to raise and lower the sails with their plaintive “We need bodies!” After a few days, I take a quiet pride in the tension I feel in my muscles and slightly stinging palms from handling the lines. I’ve even learned some of the rigging’s dense vocabulary, my eyes instinctively darting to the “jib” or “mizzen sheet” when a call comes for help.

Our efforts are rewarded with a seemingly endless procession of food, from fluffy blueberry pancakes to lunchtime chowder and dinner fajitas, all prepared, from scratch, by chef Bradley on a wood-burning stove in the tiny galley. Still, the repeat passengers most eagerly anticipate the lobster bake, generally agreed to be the highlight of each cruise. Finally, on Thursday word goes around that tonight is the night. But where?

As we sail between the uninhabited Calderwood and Burnt Islands, off North Haven, Captain Dennis lets a counting rhyme decide where to anchor. Burnt Island wins and we’re soon lowering the rowboat and paddling ashore.

Burnt Island is connected to North Haven at low tide, but for now, the island is untethered and we have it all to ourselves. Following a trail marked by lobster buoys strung from trees, I circle the entire island, walking through forest where old man’s beard lichen hangs from spruce and colourful wildflowers carpet the ground.

Back at the beach, I arrive to see lobsters already steaming over a fire in a seaweed-covered pot. The crew had bought them that morning on Swan’s Island, off which we’d anchored the night before, a small town home mostly to lobster-fishing families. We sit on the deserted island, enjoying our simple dinner of fresh seafood dipped in melted butter, and look across the water to the Angelique: it’s a scene that conjures the spirit of sailing’s golden age.

Each MWA vessel is independently owned by its captains, who are all dedicated to their preservation. Five of the sailboats are National Historic Landmarks, while the Angelique, a 130-foot ketch built in 1980, is modelled after a circa-1880 English fishing trawler.

There’s nowhere else you’ll find something like this, where you can go out and sail these vessels, says Captain Dennis. “I’ve been all over the world and seen traditional boats [that have] someone taking your money when you walk on board to get a tour around the deck,” he explains. “They’re all dead.” His boat stays alive by taking passengers out.

I’d never had much interest in cruising before. Big ships seemed impersonal and destructive, while yachts were only for the wealthy. But this one-of-a-kind trip hit a sweet spot. A Maine windjammer cruise, it turns out, contains all my favourite things about travel: history, heritage and a slow journey to places on the edge, with a sense of possibility and adventure.

Writer Karen Gardiner travelled as a guest of Maine Windjammer Association, which did not review or approve this article. The Star understands the restrictions on travel during the coronavirus pandemic. But like you, we dream of travelling again, and we’re publishing this story with future trips in mind.