Last Updated on June 3, 2021 by Jim Ferri
Sailing on a windjammer in Maine is the dream of many. It’s also quite doable…
Estimated reading time: 12 minutes
By Jim Ferri
For many years I’ve wanted to sail on a large boat. Finally, I lived my dream on a windjammer in Maine.
Undoubtedly, Windjamming is a thriving business up on the Maine coast. The Maine Windjammer Association represents 10 traditional tall ships, all privately owned. Surprisingly, six of them are National Historic Landmarks, ranging in size from 65-132 feet, carrying anywhere from 20-40 passengers.
Windjamming in Maine Aboard a Historical Ship
I set sail on the Timberwind, a National Historic Landmark and one of the smaller ships in the fleet. We sailed out of Rockport for four days and three nights about Penobscot Bay with owner and Captain Bob Tassi.
Rockport is a little town about halfway up the Maine coast. When I arrived there I wandered about a bit before going down to the little harbor and the Timberwind. Since we wouldn’t be leaving until morning I drove to nearby Camden and had dinner before returning to the boat.
Every night small kerosene lanterns were placed about the deck. Later, two of the crew, relegated to night watch, slept on the deck in their sleeping bags. Accommodations below deck are very simple. I awoke a few times during night but for the most part had a comfortable sleep.
When I got up at 6 AM the next morning I brushed my teeth, got dressed and went up on deck. There I found the two crew from night watch and another crew member just getting ready to start the day. Coffee was ready and the cook was already preparing breakfast on his woodstove in the galley.
With coffee in hand, I found myself content just to sit atop the main cabin admiring Rockport’s picturesque harbor. It was a cloudy morning and there wasn’t a sound except the squawking of an occasional gull. Around the placid harbor I watched the scores of boats slowly bobbing at anchor.
Although the Timberwind can carry 20 passengers, it turned out there were only three of us onboard for this trip. After a while two other guests appeared on deck, a couple from Belfast, a small town further up the coast.
Together we had breakfast at about 8 o’clock (meals are served family style aboard the windjammers in Maine). After we finished, we were followed by the crew who had been preparing for our departure.
“All Lines Off – No One Gets Their Money Back Now!”
At 10:30am, with Captain Bob calling out commands, we got ready to depart Rockport. The crew cast off our on-shore power connection, then the bow and stern lines. Captain Bob called out “All lines off – no one gets their money back now!”
Since we were powered only by sail, Timberwind had to be towed by a small yawl to the middle of the harbor. I watched as the crew stood by at different areas of the boat ready to hoist the sails. With the Captain calling out commands, always repeated by the crew, the sails went up. We soon were gliding across the harbor past numerous multicolored lobster buoys and out onto Penobscot Bay.
Windjamming in Maine, Relaxing With the Captain
Sailing is relaxing since there’s no engine noise and as we slid across the bay. In fact, I only heard the clanging of a buoy in the distance. I went back to the stern and spent some time with Captain Bob, wanting to know more about him. Bob, it turns out, is a former Grammy-Award winning music engineer and producer who grew up in California. He sailed the Pacific and fell in love with Windjammers when he took his family on a vacation to Maine.
After an hour of conversation with him about his life, and life in general, the ship’s bell rang four times. It was the cook calling us all together for lunch, with the guests eating before the Captain and the crew. He had set a huge pot of freshly cooked, delicious minestrone soup on top of the main cabin, along with a salad, homemade breads, lemonade and iced tea. Sitting in the sun, sliding past Maine’s 3,000 islands, I felt I’d never been in a better dining room.
Cruising About Penobscot Bay
We spent the rest of the day cruising about Penobscot Bay admiring the spruce-clad islands, rushing past countless lobster buoys and an occasional seal who would poke its head out of the water to get a look at us.
Guests onboard windjammers in Maine can participate if they’d like – hoisting sails, taking a turn at the wheel, helping out in the galley – but I took a more vegetative approach, lazing about, taking photos, chatting with Bob, waiting for Eric’s next trip up from the galley.
It was June 21, the summer solstice, and we dropped anchor that evening among a group of islands about a mile off Stonington, a town on beautiful Deer Island. After dinner the couple from Belfast and I lazed about and watched a beautiful moonrise over the water. At that moment it just seemed like things couldn’t get any better. But it did the next day.
Setting Sail for Pretty Stonington
On Saturday morning the crew of our windjammer hoisted Timberwind’s anchor and set sail for Stonington. It’s one of the picturesque fishing villages on Deer Island. It’s a beautiful, quaint little town, the kind you find on Maine postcards. Even its little post office, Stonington, ME 04681, is postcard worthy.
Shortly, we saw that the little town is a potpourri of picturesque old houses and buildings. Early-summer wildflowers in bloom everywhere. It’s a very quiet place and the only sound I could hear, apart from a very occasional passing car, was the puttering of a lobster boat moving about the harbor.
I walked down West Main Street to the post office and saw only three people. Along the way I passed Susie’s Scissor Shack, a tiny little clapboard-covered dollhouse-like place where small American flags poked up from the bright gerbera daisies in its window boxes. Soon I passed Island Fishing Gear and Auto Parts a half block away.
If you’re aboard any of the windjammers in Maine, you’ll find that Stonington is ground zero for lobster men and, in addition to the many lobster boats, traps and buoys I saw all around, I also saw an inordinate number of cars with kayaks on their tops, attesting to how popular sea kayaking is in this little corner of New England.
In addition to the lobster paraphernalia and kayaks you can’t help but also notice the scattering of antique shops and galleries. While heading back to the harbor to meet our yawl boat a block from the pier I was drawn to one of them by the scores of lobster buoys hanging on the side of the house as well as the antiques on the lawn out front. For a few minutes I poked about the hodge-podge inside and the clam baskets ($10 small, $12 large) near the porch, before continuing on down to the pier.
A Fabulous Maine Windjammer Lobster Bake
All of the windjammers in Maine in the association feature a lobster bake and when we left the island we set sail for Two Dory Island where Captain Bob has planned ours. Two Dory turned out to be a perfect spot and the highpoint of our cruise, as I imagine other islands are for those on other ships, as well.
After we dropped anchor off shore we waited aboard as the crew ferried provisions the few hundred yards to the small beach. The bay was multi-hued blue, flat and shimmering, and the sun was still high in the early summer sky despite it being late afternoon. Looking at the scene my Belfastian friends and I eagerly anticipated what was to come.
Along with Captain Bob the three of us soon landed on the little islet, being able to keep our feet dry by stepping out of the boat onto a rocky outcrop. The scene…the Timberwind at anchor in front of us, other little islands all around, the sun shimmering on the water… looked like a seascape you’d see in an art gallery in New York or San Francisco. I was captivated by it but soon became more mesmerized watching Eric and the crew put together the lobster bake, complete with fresh seawater and seaweed.
Cheese and crackers; baby carrots, celery sticks and tomatoes with a dip; potato chips and watermelon were soon spread across a rocky outcrop. The crew shucked the corn, the lobsters were dropped into the water and in no time at all we had an iconic New England meal set for us. Lobster bake nirvana… and all-you-can-eat.
Setting Sail for Pulpit Harbor
Once back on board, Bob set sail for Pulpit Harbor on North Haven Island, a tiny bay which we soon realize is not as secluded as Two Dory. A few large sailboats had already dropped anchor and another Maine windjammer was cruising in behind us. Even though cocktail hour is already in full swing on some of the boats, everything was still very quiet.
After lulling about for a while, we finished our evening down in the galley playing board games around a table that had been shoehorned into the interior of the bow. Out of the dozen or so games available, we broke out a game called “Fact or Crap,” a trivia game pretty well described by its name. All in all, it was a pleasurable evening aboard our Maine windjammer that capped a very pleasurable day.
We hoisted anchor Sunday morning and headed back to Rockport and I found that even the return trip was quite enjoyable, just lazing on the Timberwind absorbing the beauty of my surroundings.
But I think that the best part of the trip wasn’t the beauty of Penobscot Bay, or wandering about quaint Stonington or even that delicious lobster bake. All in all, the best part was the simplicity of the experience…the getting away from the phone, the TV, the computer, all the technological annoyances that have become such a part of our lives.
The windjammers in Maine took me back to another time, a time when people were able to appreciate the simple things in life…something that today all too many of us consider a luxury.
I would certainly guess that I’m not the only one who feels that way. A few hours after our return to Rockport Captain Bob set sail again with a full charter of 20 guests.
If you go:
If you enjoy the ocean, New England, and think you’ll enjoy windjammers in Maine, this is a great experience whether you are a solo traveler, a couple or an entire extended family. The vessels sail from late May to mid-October with a number of “Gatherings of the Fleet” (Schooner Gam, the Great Schooner Race, Maine Windjammer Parade, etc.) taking place from June through early September.
The ships of The Maine Windjammer Association carry between 20-40 passengers on long weekend trips to six-day cruises. Prices range between $400 and $1,188 (including all meals) depending upon the ship and the length of the cruise.
The Maine Windjammer Association
Post Office Box 1144
Blue Hill, ME 04614
Tel: (800) 807-9463