Windjammer Cruises on Maine’s Penobscot Bay

Last Updated on April 4, 2024

Editor’s note: This article was first published a few years ago, but I have updated it and am re-publishing since it continues to be a great experience for today’s travelers. I think you’ll agree – JF.

Estimated reading time: 13 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 9 traditional tall ships, all privately owned. Surprisingly, five 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 the owner and Captain Bob Tassi. (Note: the Timberwind has since been sold to the Portland Schooner Company and is now berthed in Portland, ME).

Rockport is a little town about halfway up the Maine coast. I wandered about a bit when I arrived before going down to the little harbor and the Timberwind. Since we wouldn’t leave 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 the deck are straightforward. I awoke a few times during the night but, for the most part, had a comfortable sleep.

When I got up at 6 AM the following day, I brushed my teeth, 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 wood stove in the galley.

A Picturesque Harbor

With coffee in hand, I was content 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, scores of boats bobbed at anchor.

Although the Timberwind can carry 20 passengers, only three of us were on board for this trip. After a while, two other guests, a couple from Belfast, a small town further up the coast, appeared on deck.

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. The sails went up with the Captain calling out commands, continually repeated by the crew. We soon glided across the harbor, past numerous multicolored lobster buoys, and out onto Penobscot Bay.

Windjamming in Maine, Relaxing With the Captain

The sail was relaxing since there was no engine noise 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 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 large pot of freshly cooked, delicious minestrone soup on top of the main cabin, along with a salad, homemade bread, 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 that 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 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 Windjammers in Maine tend to visit. 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 were in bloom everywhere. It’s a tranquil 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, which seemed a bit incongruous.

Ground Zero for Lobstermen

If you’re aboard any of the windjammers in Maine, you’ll find that Stonington is ground zero for lobstermen. And in addition to the many lobster boats, traps, and buoys I saw all around, there was also 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 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 and the antiques on the lawn out front. For a few minutes, I poked about the hodgepodge inside and the clam baskets ($10 small, $12 large) near the porch before continuing 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 had planned ours. Two Dory was a perfect spot and the high point of our cruise, as I imagine other islands are for those on different ships.

After we dropped anchor offshore, 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 would come.

Along with Captain Bob, we soon landed on the little islet, keeping 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 in an art gallery in New York or San Francisco.

It captivated me, but I soon became more mesmerized watching Eric and the crew assemble 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 an all-you-can-eat on my Windjammers in Maine cruise.

Setting Sail for Pulpit Harbor

Once back on board, Bob set sail for Pulpit Harbor on North Haven Island, a tiny bay we soon realize is not as secluded as Two Dory. A few large sailboats had already dropped anchor, and another Maine windjammer was cruising behind us. Even though cocktail hour was already in full swing on some of the boats, everything was still tranquil.

After lulling about for a while, we finished our evening 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. Overall, a pleasurable evening aboard our Maine windjammer capped a pleasant day.

We hoisted anchor Sunday morning and headed back to Rockport. I found that even the return trip was quite enjoyable, just lazing on the Timberwind, absorbing the beauty of my surroundings.

But I think the best part of the trip wasn’t the beauty of Penobscot Bay, wandering about quaint Stonington, or even that delicious lobster bake. The best part was the simplicity of the experience… getting away from the phone, the TV, the computer, and all the technological annoyances that have become such a part of our lives.

The windjammers in Maine took me back to another time when people could appreciate the simple things in life…something that today, all too many of us consider a luxury.

I would guess 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.

FAQs

Are Windjammer cruises safe?

Yes, each windjammer is Coast Guard Certified. Certification includes drug testing of the crew.

What Is the cost of a Windjammer Cruise?

Cost varies greatly (see below) depending upon the vessel and the length of the cruise. Some cruises are two-hour sails, others are multi day.

What companies offer multi-day Windjammer cruises in Maine?

Maine Windjammer Association
https://www.sailmainecoast.com/
Tel: (800) 807-9463
The Maine Windjammer Association has a fleet of 9 ships sailing from either Camden or Rockland, ME on 3 to 9-day sailings.
Prices vary depending upon the ship and time of year. You can also book a last-minute cruise by contacting the vessel directly through the association’s fleet page.

Maine Windjammer Cruises
https://mainewindjammercruises.com/
(800) 736-7981
Maine Windjammer Cruises has two ships sailing from Camden, ME on multiple cruises from 3 to 7 days. Established in 1936, it prides itself on being the original Windjammer Fleet. Prices range from $875 for a three-day pre-season cruise to $1980 for a four-day cruise in-season.

What companies offer two-hour sails?

Portland Schooner Company
https://www.portlandschooner.com/
Tel: (207) 766-2500
South of Penobscot Bay in Portland, ME, the Portland Schooner Company offers two-hour public Windjammer cruises on Casco Bay.

Prices for a two-hour public sail:
Morning Sail: $55 adult / $39 infant/child, 0-12
Afternoon Sails: $60 adult / $44 infant/child, 0-12
Sunset Sail: $65 adult / $65 infant/child, 0-12

Schooner Eleanor
https://www.schoonereleanor.com/
Tel: (207) 967-8809
Further south in Kennebunkport the schooner Eleanor offers two-hour sailings. Morning and mid-day sales are $75 per person; evening sales $85 per person. Since guests are allowed to bring along their favorite beverage on the evening sail, you must be 16 years or older to board.

Interestingly, since sails are dependent on the weather and tides, deposits are not required, and payment is collected after the sail.

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