“With most vacations, you’re checking off the boxes, your to-do list of experiences. Here, we have wild cards, like the weather, so you don’t know how things will unfold,” says captain J. R. Braugh of the schooner Ladona. “That’s what makes it an adventure.”

Such are the rewards of a windjammer trip out in Maine’s Penobscot Bay. With some 2,000 pine-studded islands, and numerous quiet coves to explore, along with storied fishing villages like Stonington and Isle au Haut, these waters are a cruiser’s dream. Do it on a classic, 1922 racing yacht like the schooner Ladona (pronounced lah-DOH-na), and you’ll do it in style. This 83-foot, two-masted vessel sails out of Rockland with a crew of five, and 16 guests, from May through October. This is its first season under sail after a 95 percent rebuild, and it’s a vision of polished teak and brass, with a good-sized galley and lots of natural light. Expect admiring looks as you cruise into ports like Castine and Boothbay Harbor aboard the Ladona — kind of like tooling around Boston in a vintage Porsche. But there’s no roaring engine noise: the Ladona travels under sail, not engine, at least 90 percent of the time, according to Braugh.


“We’re trying to bring some luxury to the windjammer experience,” says Jane Barnes, who co-owns the Ladona with her husband Noah (they also own the Stephen Taber windjammer) and Braugh. They bought it in July of 2014 and have been making it ship-shape ever since. While the cabins are definitely snug — this is a windjammer, after all — they’re nicely turned out, with hot and cold running water, tiled showers with rain heads (there are three heads, or bathrooms, aboard ship), and even monogramed bathrobes. “Our goal is to offer more comfort, at a higher price point (than typical windjammer cruises),” Jane Barnes says, noting that three of the cabins offer queen-sized beds.

The smaller number of guests aboard this vessel means that the galley can offer more plated meals, and do a rolling breakfast (from 7 to 9 a.m. each day) with made-to-order omelets, as opposed to having guests line up for chow time. A typical dinner menu might feature hand-rolled ravioli with fresh sage and brown butter, followed by Tuscan beef (rolled with roasted red peppers, prosciutto, and fresh basil), along with roasted local hakurei turnips with fennel-infused olive oil and fresh fiddleheads. Of course, there’s a lobster bake on every cruise, a highlight of the Maine windjammer experience. They also do some specialty trips focusing on wine (Jane Barnes works in the wine business), and “bluegrass and brew” cruises with live music. There’s even one called “Parts Unknown,” in which the itinerary is based on the captain’s whim (hint: he really likes Isle au Haut. “It’s like a time capsule, off the beaten path,” he says.)


But unpredictability is always part of the deal when you’re sailing on a windjammer. The direction of the wind determines where you’ll go and when you’ll get there. On a six-day trip, you might get as far north (east, on sailing charts) as Bar Harbor and the Schoodic Peninsula, Braugh says, or as far south (west) as Boothbay Harbor or Monhegan Island. Shore excursions (self-guided) are a fun way to see tiny villages and seaports that are off the well-worn tourist track of Route 1.


“If you’re up for an adventure, a windjammer is great, because no two trips are alike,” says Barnes. It’s also a great way to be semi-unplugged. Guests can usually check in with friends and family as needed, since there is cell coverage about 70 percent of the time, Barnes says. “Most people who come aboard want to get away, so they are pretty happy to leave their phone in their cabin, or only use it as a camera,” she adds.

Not to mention, you get permission to be lazy, with no decisions about what to do and where to go. Someone else is sailing the boat, and someone else is planning the menu and cooking for you. Your job is to soak up the glorious views of deep-blue-Atlantic-meets-azure-sky, and to crack open your lobster when the time comes. Oh, yeah, and to wave graciously as passersby take photos of your glorious racing yacht and its good-looking cast of characters.

For more information, visit www.schoonerladona.com. Sails from mid-May through Columbus Day on 3- to 6-day cruises. From $1,000 per person. Age 16 and over only. For information about the other vessels in the Maine Windjammer Association (there are nine in all), visit www.sailmainecoast.com. Race Week is July 3-9, with race day on July 8th.

Diane Bair and Pamela Wright can be reached at bairwright@gmail.com.