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After dealing with the process of getting our daughters squared away for their next year in college, my wife, Kanako, and I deserved a break. We both love sailing but, to be perfectly honest, summer in Florida is just too hot to be on an open boat. We needed to find a place with good winds and cool temps! Trouble is, summer heat waves are now a regular occurrence across much of the U.S.; it’s hard to find an area below 43 degrees north that doesn’t see daytime highs in the mid- to upper 90s. To escape these roasting regions, we had to find a cruise well north of the Mason-Dixon Line.
After some hard thinking, I recalled a day in 2013 spent taking pictures aboard American Eagle, a traditional wooden schooner participating in Maine Windjammer Association’s Great Schooner Race in Penobscot Bay. At 123 feet LOA, she was the largest sailing vessel I’d ever been on – gaff rigged, natural fiber lines, no winches. And although captain and crew managed operation of the ship, paying passengers participated in the race. She sliced through the waters like a dream, and I thought that, surely, someday I’d return.
Schooner Country
The schooners in the MWA are individually owned and offer single- to nine-day cruises, June through September, embarking from one of several Maine ports. I selected a week aboard Heritage and told my wife to start packing. “Remember,” she reminded me with a stern look, “I don’t like hot weather.”
Unlike most other cruise ships, Heritage doesn’t share its itinerary before departure. “This is an unscripted trip with no set destination,” I was informed by office manager and crew member Beth Sailor (yes, that’s her real name). “We’ll choose our anchorages based on weather and the winds that take us there, and any shore trips that we’re able to take will also be dictated by the winds and tides.”
Most of the 16 passenger cabins contain two bunks, a 120V power outlet, sink, light, and not much more. No Wi-Fi, no swimming pool, no casino. Perfect. “Relax,” I told my wife. “It’s Maine. Wherever we go, it’ll be great.”
After a three-plane trip beginning at 0500, we drop out of the sky onto Knox County Regional Airport and Uber the last 10 minutes to downtown Rockland, a small town that serves as homeport for most of the windjammer fleet. I step out of the car, the temperature is 30 degrees cooler than in Florida, and I love this place already. Once aboard we’re escorted to our cozy cabin in the forepeak as our fellow passengers amble down the gangway and find their own cabins.
Coming down the ways in 1983, Heritage is 145 feet LOA with an 8-foot draft and takes 30 passengers. If the wind doesn’t cooperate, there’s a diesel push boat, but everything else is traditional: belaying pins, wooden blocks, and pitch on the running rigging. I wander around looking for fiberglass, but there’s none; nothing but hemp, metal, and wood. We’ve stepped aboard a time machine.
This is an unscripted trip with no set destination,” I was informed by office manager and crew member Beth Sailor (yes, that’s her real name). “We’ll choose our anchorages based on weather and the winds that take us there, and any shore trips that we’re able to take will also be dictated by the winds and tides.
Crew Briefing
In the morning Captain Ben introduces the crew, gives the safety briefing covering crew overboard, life preservers, life rafts, EPIRB, and abandon-ship procedures. And just like that, the sails are hoisted and we’re off into the bay on one of the nicest days of the summer, leaving Rockland Lighthouse to port and Owls Head to starboard.
A steady southwest breeze pushes Heritage on a line heading east, and soon we’re squeezing through the narrow pass between Crotch Island, Maine’s last active island quarry, and Stonington on Deer Isle; Valhalla to sculptors, painters, musicians, writers, and anyone who treasures the outdoors. It’s Maine’s largest lobster port, and with its steep, rocky hills, every home has a great view of the bay. When John Steinbeck visited here in 1960, the island profoundly impacted him. “This Isle is like Avalon,” he wrote in his esteemed travelogue “Travels with Charley.” “It must disappear when you are not there.” Indeed, at 6 knots it vanished quickly from sight.
I had some misgivings about being placed in the forepeak before the mast; after all, that’s where the common seamen have always bunked. And they were realized the following morning near Swan Island when “Joe” the 1921 deck engine roared to life and the ear-splitting, bone-shaking rattle of the anchor chain played out directly above our heads. From then on we got up early and out of the cabin.
Down East Daze
Mainers, as they refer to themselves, make no apologies for foul weather – or anything else for that matter. With two beautiful days in the bank, we were due for some dirty weather, and, boy, did we get it.
The day dawned to the thickest fog I’ve ever seen. From the bow, a hand-operated horn bleated out its plaintive song. The sounds of the sea, normally so easy to distinguish, become jumbled in the thick haze. It’s easy to get the uneasy feeling that everything out there is on a collision course with our vessel. Every so often the sharp-eared crewman would jump and shout, “Motor vessel approaching at 2 o’clock!” and Captain Ben, who’d be at the wheel for the entire six days with only short relief, would strain his eyes and prepare to take evasive action.
These guys are good.
You’re probably wondering about those infamous lobster traps. Yes, Maine is chockablock with them, and in East Coast waters we learn to swerve around the ubiquitous crab pots or they’ll wrap around our props. But Heritage’s push boat prop is enclosed in a cleverly designed cage, allowing the schooner to sail a straight line without regard to their positions – good to know, as the water is 60 F.
Eventually the fog clears just enough for us to see Maine Maritime Academy’s schooner Bowdoin coming around the bend, returning from its 4,500 mile Arctic voyage to Greenland, on the last leg to Castine. Crewed by students and staff, they collected environmental DNA to monitor and measure biodiversity, making it as far as the 70th parallel. “Load the cannon,” shouts Captain Ben. We exchange courtesy blasts and wave as we pass, cellphone photo apps on both vessels clicking madly.
The anchor drops for the night in Bass Harbor on Mount Desert Island, and the boats are lowered for one and all to have a row. Kanako and I head for a distant rock and get a lesson about paying attention to the tidal predictions, even when your draft is less than a foot. We huddle in the stern as I push like hell with an oar to get us unstuck. We return to the mothership in the last of the evening light with the sound of loons having a hearty laugh on us.
Are you up for some windjamming?
The Maine Windjammer Association consists of the largest fleet of traditional sailing vessels in North America. Each of the nine unique ships is individually owned by U.S. Coast Guard-licensed captains and operated to preserve and promote the state’s historic windjammers. Homeports are in both Rockland and Camden. Some are schooners, some ketches, while others are purpose-built for cruising. Prices start at $795 per person. To learn more, contact the association at info@mainewindjammerfleet.com or (800) 807-WIND. sailmainecoast.com
Schooner Heritage
As part of the Maine Windjammer fleet, the 2025 Heritage sailing season kicks off with six cruises in June and continues through September. A 35% deposit per person is required at the time of booking, with the balance due six weeks before boarding. Contact Schooner Heritage at info@schoonerheritage.com, (800) 648-4544. schoonerheritage.com
The author edged out onto the bowsprit of Heritage, camera in hand. Photo, Robert Beringer
Capt. Sean Grimes and crew member Beth Sailor in the galley. Photo, Robert Beringer
Vanishing Act
They say that fog comes in on little cat feet, but out here it’s more like a million snakes slithering across land and sea. The tendrils creep in, slowly at first, then by the time dinner is done, the shore – and everything else – is gone. The temperature drops, and I’m grateful for the extra wool blanket in our cabin.
Progressing southwest the following morning with running lights ablaze through another typical misty Maine day, we cross paths with a wraith in the distance. “Is it real or the Flying Dutchman?” I wonder aloud. “That’s the Angelique,” declares David, the mate. Even though the ship is barely visible, these crew members know all the sister schooners in the Windjammer fleet.
We’ve been promised a lobster bake on the beach, and after anchoring by Babson Island, the deck crew begins shuttling passengers to shore while the galley crew gathers driftwood and seaweed to prepare our meal. Here we learn another primary difference between a cruise ship and a traditional schooner: The gig has no motor; passengers provide the propulsion. I’ve always used oars to row the dinghy on my boat, but it takes some practice to get the hang of it when you are one of eight galley slaves.
Dinner on the beach is outstanding. I’ve never eaten fresher, tastier, or larger lobsters in my life. Purchased directly from fishermen before departure, they’re kept in a galvanized ice bucket on deck with a pump circulating seawater, then transferred to plastic bins in the ocean at night. In fact, I can’t think of one meal or snack on board that wasn’t delicious. Sean and Beth run a first-rate galley; I sensed that several of the repeat passengers are OK with the sailing experience, but it’s the cooking that keeps them coming back.
Going Ashore
Babson is part of the Maine Coast Heritage Trust, an organization that has preserved hundreds of iconic islands, critical wildlife habitats, and coastal watersheds around the state, conserving them in perpetuity for public use. So there are trails in most of these places. Several passengers make for the island’s loop trail after dinner, and we’re treated to a great hike through a spruce and northern hardwood forest with no sign of humans but a footpath. Irked ospreys chirp at us from their nests in the trees. At sunset we row back to Heritage while being serenaded with sea chanties from the crew.
Like a switch, the clam-chowder fog is back on again in the morning for the quick trip to Brooklin where we wander around the Wooden Boat School to witness the amazing things they do with wood. Visitors are welcome, but a sign reminds us not to disturb classes in progress. Quietly we drift around the old buildings as future boatbuilders drill, saw, and sand their various creations. Another adage about this state is, if you want to get to Maine, you have to walk in the rain. Sure enough, it began to pour, sending us scurrying back to the dock in time to see sister schooner Stephen Taber finish its visit, weigh anchor, and vanish like a ghost.
Crew member Roy keeps silent watch as Heritage slips through the Maine fog. Photo, Robert Beringer
Homeward Bound
The weather clears for a penultimate day of easy sailing to Islesboro, where we anchor near Dark Harbor, sharing a sublime sunset with multimillion-dollar mansions as several of us hearty souls take a plunge in the chilly water. The weather holds for heading back to Rockland in the morning, and the galley crew lays out a splendid champagne brunch for our triumphant, if sad, return.
Approaching the harbor, Captain Ben gives the order to drop and furl sails for the final time. We gather our bags and shake hands all around. I try not to think about heading home to the heat and how fortunate these schooner people of the Windjammer fleet are, to spend the whole summer season sailing in the mists of the Pine Tree State.