Sailing Maine’s Penobscot Bay on a Timberwind Music Cruise

Captain Bob Tassi playing the accordion

I am sitting on Warren Island in Maine’s Penobscot Bay, watching a mountain of lobsters redden on an open fire. Bob Tassi — ship captain, Grammy-award winning recording engineer, and musician — is playing songs written by his grandfather on the accordion. In the protected waters to the east of the island, the schooner Timberwind, a national historic landmark, rocks gently on the almost glassy waters of a still August evening. I hear the music of the accordion, the sound of quiet conversations, the crackling of the fire, laughter. No video game noises. No TVs. No cell phones. No sports drone in the background. No traffic.

Most people consider themselves lucky if they fall in love with one job in a lifetime. Bob Tassi has done it twice. Being owner and captain of the Timberwind is an unlikely second career for the former Grammy-award winning recording engineer, who traded one dream job — working with some of America’s biggest recording artists — for another — captaining an historic tall ship. But sitting with him on this quiet August evening as the lobsters bake and the music spreads across the island, I can easily see why.

In Your Bucket Because…

  • You’ll get a chance to experience classic sail-powered sea travel on the real thing: a traditional schooner.
  • It is one of the most restful, peaceful vacations on the planet.
  • You like the idea of going where the wind blows you.
  • Good for: Lovers of wild places, simple living, and music.

Music to Sail By

Timberwind in Rockport, Maine

Tassi didn’t quite get away from Nashville clean: He left part of his heart back in a recording studio. So every once in a while, he combines his two passions and invites recording artists he worked with at Warner Brothers to join specially designated music cruises and play for the 20 or so guests. In between the intimate evening concerts, the daytime cruising, and the first rate meals, you may be lucky enough to hear Captain Bob pick up his own guitar or accordion — or hear accounts of what it was like to work with artists like Johnny Cash and Barbra Streisand.

UPDATE: Since this article was written, the Timberwind is no longer part of the Maine Windjammer fleet. Readers interested in sailing with Captain Bob in 2014 will find him at the helm of the schooner Eastwind in Bootbay Harbor. Readers interested in experiences similar to those described in this article can check out the other Maine Windjammers, which offer themed programs featuring music, geology, storytelling, and foliage.

A little night music aboard the Timberwind with Kevin Welch.

On this particular cruise, it was Americana artist Kevin Welch who held the attention of about 20 guests in intimate evening performances. We sat around a corner of the boat, listening as Kevin played songs off his new album, A Patch of Blue Sky  along with a variety of tunes running the range from country rock to ballads. A songwriter who offers writing classes at his Austin home, Kevin’s tunes combine familiar elements of country, rock, blues, and folk, alchemized into songs that echo back to a common Americana sound and theme, yet are sharply smart and contemporary. During the cruise, he was happy to talk about songwriting and performing and, really, all things musical — manna to other music lovers, whether professional or amateur.

Guests (and crew) are welcome to bring instruments on board, so I brought a small battery-powered keyboard (there are no outlets) and my partner, David, brought a guitar and a ukulele. A couple of other guests and crew also had guitars, so we pulled out our instruments, pooled our chords, and happily jammed. Kevin joined in, treating us to some of his tunes while we improvised along with him.

Camping on the Water

The first thing you need to know about cruising on a Maine Windjammer is that we’re not talking luxury: With tiny cabins (and by tiny, I mean the size of a New York City bathroom), limited  electricity (lights, yes; cell-phone chargers, no), and shared marine toilets, it’s a little like camping on the water. Nonetheless, the cabins have good headroom, comfy bunks, and a bit of storage space. David and I quickly mastered the small-ship skill of making use of every available square inch, and managed to fit our two small carry-ons, the guitar, the uke, and the keyboard under the beds and in the corners of our cubbyhole.

Timberwind is an historic Maine tall ship.

Timberwind is a local lass, built in Portland in 1931. For 38 years, she was a pilot ship, guiding larger ships into port. On retirement from that gig in 1969, she was converted into a passenger ship, and in 1992, was designated a National Historic Landmark.

She’s also fast: The crew spoke lovingly not only of her lines and looks, but of her ratios of length (100 feet), keel (deep), and sail size (lots of sail for her length), which meant that this is a ship that can move on the water. When they compared her to other ships in the Windjammer fleet, you could hear a bit of rivalry — and the assurance that comes with knowing you’re on a winning team. On days when the wind is up, they say, she will virtually race across the bay, tipped so far to one side that the gunwales are almost touching the water. I report (with a bit of relief) that the winds during our cruise were quite a bit gentler, which meant that we weren’t going anywhere especially fast. That is part of the beauty of a Timberwind itinerary: there really isn’t one.

“We go where the wind takes us,” Tassi declares, although the winds seem to cooperate fairly frequently to bring guests to Warren Island State Park for the traditional lobster feast.

It was my second cruise on a Maine Windjammer, and both had this in common: I didn’t know where the time went. With perfect weather, a great deal of the day went to simply staring out at the water at the islands and shorelines of Penobscot Bay.

Doing dish duty at sea

We occasionally helped with raising and lowering sails and with chores like chopping vegetables or washing dishes after meals. Some guests did yoga. Some read. All of us chatted: It was a companionable group. Tassi’s ship welcomes families — a policy dating back from when he had his own kids on board — but our cruise was all adults.

Chow time on the Timberwind

Something else Maine Windjammer cruises have in common: Fantastic food. I do not know how miracles are performed in a kitchen the size of the interior of an ancient VW Beetle. Maybe he had some of Harry Potter’s house elves working in there, but our chef managed to pull out steaming loaves of homemade breads, hearty soups and stews, salads, and copious amounts of home-made deserts. Not to mention that signature Windjammer dinner: a Maine lobster bake, with all the lobster you could eat. (Alternatives are available for those with allergies or other preferences.)

There’s something about the bracing air and living outdoors that magnifies appetites, and I suppose that that is one way that sailing on a Windjammer is like camping on the water. The simple sleeping arrangements and shared heads are another, but the comparison goes much deeper than that, touching on something both more important and more essential. By subtracting all the trimmings of modern life and all the distractions of contemporary vacations (Ziplines! Cave tubing! Animal parks!) a cruise on a traditional tall ship brings  into focus simpler, quieter fundamentals that are too often crowded out of our lives. It made room for idle conversations that wandered and turned and went somewhere unexpected. It made time for us to really look, and to really see: the shape of the sails, the color of the water, the glinting gold of evening light. And, on this particular cruise on the Timberwind, it made room for music.

Nothing to do but watch the ever changing islands.


  • We had excellent weather, but the Maine coast can be rough, so bring a rain jacket and a couple of warmer layers.
  • The ship is docked in Rockport, Maine: There is only one restaurant (evenings only) and few services. Boarding time is in the evening the night before departure, and snacks are served the first night. If you want more substantive food, buy it before you get to Rockport.
  • Overnight parking is available for a fee at the marina, or you can be shuttled to a free parking area for the boat’s passengers..
  • Bring ear-plugs: The sound barriers between cabins is minimal.
  • Families are welcome on the Timberwind, but you’ll need to be the judge of how your  kids will handle the close quarters and the lack of electric conveniences.
  • Schedules available at the Timberwind website.

Classic Maine Windjammer lobster dinner

Average rating for this trip


  1. Brent Boyington says

    Hi Karen
    Last year was out third year out on the Timberwind and the second year with Kevin W. All of the trips were super. Good food. Great company. The best scenery. I recommend this trip to anyone who has the urge to sail. You can watch or pitch in and help. Hope to see you again.
    Have a great one,
    Brent and Jane


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