Explore Coastal Maine Aboard a Windjammer

A four-masted schooner with maroon sails crosses open water.
The Margaret Todd under sail in Bar Harbor. Photo © Brian Snelson, licensed Creative Commons Attribution.

In 1936, Camden became the home of the “cruise schooner” (sometimes called “dude schooner”) trade when Captain Frank Swift restored a creaky wooden vessel and offered sailing vacations to paying passengers. He kept at it for 25 years, gradually adding other boats to the fleet. Now, more than a dozen sail Penobscot Bay’s waters. Rockland wrested the Windjammer Capital title from Camden in the mid-1990s and so far has held onto it.

Named for their ability to “jam” into the wind when they carried freight up and down the New England coast, windjammers trigger images of the Great Age of Sail. Most member vessels of the Maine Windjammer Association are rigged as schooners, with two or three soaring wooden masts; their lengths range 64-132 feet. Seven are National Historic Landmarks.

These windjammers head out for 3-6 days late May-mid-October, tucking into coves and harbors around Penobscot Bay and its islands. They set their itineraries by the wind, propelled by stiff breezes to Buck’s Harbor, North Haven, and Deer Isle. Everything’s totally informal, geared for relaxing.

You’re aboard for the experience, not for luxury, so expect basic accommodations with few frills, although newer vessels were built with passenger trade in mind and tend to be a bit more comfy. Below deck, cabins typically are small and basic, with paper-thin walls—sort of a campground afloat (earplugs are often available for light sleepers). It may not sound romantic, but be aware that the captains keep track of postcruise marriages. Most boats have shared showers and toilets. If you’re Type A, given to pacing, don’t inflict yourself on the cruising crowd; if you’re flexible, ready for whatever, go ahead and sign on. You can help with the sails, eat, curl up with a book, inhale salt air, snap photos, eat, sunbathe, bird-watch, chat up fellow passengers, sleep, eat, or just settle back and enjoy spectacular sailing you’ll never forget.

When you book a cruise, you’ll receive all the details and directions, but for a typical trip, you arrive at the boat by 7pm for the captain’s call to meet your fellow passengers. You sleep aboard at the dock that night and then depart midmorning and spend the next nights and days cruising Penobscot Bay, following the wind, the weather, and the whims of the captain. (Many of the windjammers have no engines, only a motorized yawl boat used as a pusher and a water taxi.) You might anchor in a deserted cove and explore the shore, or you might pull into a harbor and hike, shop, and barhop. Then it’s back to the boat for chow—windjammer cooks are legendary for creating three hearty all-you-can-eat meals daily, including at least one lobster feast. When the cruise ends, most passengers find it hard to leave.

On the summer cruising schedule, several weeks coincide with special windjammer events, so you’ll need to book a berth far in advance for these: mid-June (Boothbay Harbor’s Windjammer Days), Fourth of July week (Great Schooner Race), Labor Day weekend (Camden’s Windjammer Weekend), and the second week in September (WoodenBoat Sail-In).

Most windjammers offering 2-6-day sails out of Camden, Rockland, and Rockport are members of the Maine Windjammer Association (800/807-9463), a one-stop resource for vessel and schedule information.

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