A Windjammer Cruise on Penobscot Bay Is the Best Way to Experience Maine’s Coast

During an overcast-but-pleasant Fourth of July weekend, I sat on the rocky beach of an uninhabited islet off the coast of North Haven, Maine. As a plastic platter bearing the illustration of a lobster and trimmed with blue anchors balanced on my lap, I dug into an actual bright-red lobster that had moments before been poured out of an iron tub of boiling seawater onto a bed of kelp set on the pebbles. I’d wanted a truly iconic Maine moment, and this was it.

Just offshore, the windjammer Angelique—our old-school schooner for the weekend—sat at anchor. We’d rowed ashore earlier, along with all the contents of our leave-no-trace beach lobster bake. Afterwards we’d pack it all up and row back out to spend a tranquil night onboard, with just the local wildlife chatter and the sounds of the boat gently creaking in the secluded cove competing with the conversation of the ship’s company.

The passengers were adventurous, well-traveled folks who all had an interest in windjamming, or cruising on traditional ships with sails. We and the crew had bonded quickly over the previous two nights. The deckhands (who that season all happened to be women) seemed just as at ease making jovial conversation as they did patiently issuing instructions on how to help raise sail or safely enter the longboat to row ashore.

The thrown-togetherness of a windjammer cruise seems part of the appeal. It’s only natural to engage in banter (and plenty of nautical puns, thanks to the crew) while standing on deck during the Angelique’s daylight sails between moorings, keeping an eye out for porpoises or other sea life.

Onboard meals are bountiful—keeping the local maxim of “good food, and plenty of it.” Mornings start off with fresh-baked goods and coffee for early risers before hearty, core-warming breakfasts. Lunches of soups, salads, and more baked goods are made and served while underway, the skilled kitchen crew poring over a kerosene stove in tight quarters with a slanted deck. Dinners of roasts or fish with plenty of trimmings ensure passengers won’t be short on sustenance despite the appetite-encouraging sea air.

When I would tell friends I had booked a windjammer cruise off the coast of Maine, the response was pretty standard: “That sounds amazing, but how do you do that?” It does sound kind of clubby—like a well-kept regional secret—but that’s where the Maine Windjammer Association (MWA) comes in. Their website seems designed for travelers who have an idea of what they want to do, without knowing much about how.

Each of the nine windjammers in the fleet is captained by individual owners of the small vessels—the largest sleeps just 40 passengers. Promoting each boat's already niche experience would be difficult, so the owners formed MWA to jointly market and promote their products and agree on a standard “code of excellence” for operations, accommodations, and service.

Trips start and end in either Camden or Rockland, Maine, and include a lobster bake plus locally sourced, fresh-cooked meals onboard. Other points of consistency apply to environmental practices (sailing is already a near-zero emissions activity), crew hiring, and owner-host structure.

Aside from the basic standards, each vessel and crew have their own distinctive personality. Passengers can choose a ship that’s new or old, big or small, rustic or more luxe (the Ladona has rainfall shower heads with marble-accented flooring, for example) among other considerations. The Lewis R. French and the Stephen Taber in the fleet began life as light cargo haulers over 150 years ago; the Angelique and the Heritage were purpose-built for these very same passenger windjammer trips in the 1980s.

There are reminders that the boats, most of which are designated national historic landmarks, are from an earlier era. Some don’t have inboard engines and instead use separate “yawl boats,” the schooner version of the outboard. Others still have wood-burning stoves, from which skilled cooks manage to turn out loaves of fresh-baked bread and batches of cookies.

Travelers sold on the idea of windjamming in the protected waters of Penobscot Bay—just as visitors to Maine have been doing for generations—can head to MWA’s website to pick out which windjammer best suits their tastes. The windjammers normally spend the first night at the mooring so guests can get accustomed to the accommodations before heading out.

Accommodations are comfortable, but compact. Cabins are designed for stowage and sleeping, as guests will want to make the most of the views and camaraderie topside. All boats have shared showers and toilets; some boats have larger rooms with private facilities. All bunks have freshwater sinks and are provided linens.

Meals, coffee, tea, water, and hot chocolate are provided, too. Boats have ice chests for guests to bring their own beverages (to drink in moderation), which can be picked up the first night in port before casting off. Passengers should pack as they would for any camping trip with variable weather (layers, hat, bug spray, sunscreen) keeping in mind limited stowage.

Sailings typically depart from late May through the end of the foliage season in October. Many of the boats also offer themed cruises, ranging from lighthouses to yoga-themed sailings, but there’s one thing that won’t be found: ironclad itineraries. The vessels sail with the wind and weather; captains draw on their years of experience to chart out the best itinerary as it happens.

As we sailed past a pod of harbor seals sunning on the rocks off North Haven, Captain Dennis Gallant chewed over the best spot to anchor Angelique that evening, taking into account the wind conditions and whether he expected any fireworks displays on that July 4^th night.

Whatever spot he chose would also need to be just a few hours sail from Camden, where Angelique was due to berth by the middle of the next morning so guests could catch their flights home. We ultimately anchored in a glassy cove near Seven Hundred Acre Island and reflected on days spent hauling sail, rowing longboats, exploring island communities, and chatting with new acquaintances.

And yes, there were fireworks.