Sailing a Historic Ship on Maine’s Penobscot Bay is a Voyage
By Karen Rubin & Neil Leiberman

We are “flying” over the surface of the water at 8 knots, heeling at such an angle that one side of the ship is just about dipping into the water. But not quite. We can see through our sails on the Nathaniel Bowditch to the billowed sails of the American Eagle, another proud windjammer, following just behind for the moment.

Just a couple of days before (it seems like long ago), we were sailing out of Rockland harbor into the Penobscot Bay, with theStephen Taber off our port side, magnificently framed against the Rockland Lighthouse, a perfect picture that could have been made a century ago. As we sail further away from port, we soon feel we have indeed slipped back to that time, when the windjammers-those workhorses that carried cargo up and down the eastern seaboard–ruled these waters. Now it is mainly the lobster boats, and the lines that link the colorfully marked buoys-so thick in some parts it seems you could almost walk from one to another–to the traps below are like webs just below the surface that catch our ship, as well.

We are lucky on our trip to have a variety of weather and sailing conditions. One night, we fall asleep underneath a star-studded sky, the Milky Way laid out before us like a twinkling blanket, and wake up shrouded in a thick fog then sail into clear skies propelled by a strong wind that gives us the feeling of flying across the water, and finally, we bob through fog and choppy seas on the return to harbor.

It is a weird and wonderful feeling to be so dependent on the weather. In fact, dependent upon Nature: the tides, the current, the positioning of rocks, where nature has plunked islands and ports in its glacial sculpturing. Out here, what had seemed so basic becomes profound. You are reminded of what a small speck you are in the firmament, in the eons of time.

You appreciate things so much more. These magnificent windjammers, for example. Most of the 14 ships in the Maine Windjammer Fleet are historic vessels, and all harken back to the days of power mainly by wind and muscle (okay, there is an engine, too). Simple machines, you might think, but hardly simple. From the first moments, as we get underway, I am amazed by how much skill, knowledge and experience is involved, even though we quickly take our place on the line, or helping to crank up the anchor, and even at the helm, steering the ship with compass, and charts, and yes, the wind.

This is nothing like a cruise. It is a voyage.

“I know exactly where we are going,” Capt. Owen Dorr says when we get ready to set sail. “We will leave today at 10 and go to a nice place; tomorrow, another nice place; when we drop anchor, it’s a good chance that’s where we’ll be. Where we are-I can tell you-is directly above the center of the earth.” In other words, we will go where the wind and tide will carry us.

Most-not all-of our fellow passengers are sailors themselves who appreciated the fine design and features of the 82-foot long double-masted Nathaniel Bowditch, a historic ship which began its career in 1922 as a racing yacht (it won special class honors in the 1923 Bermuda Race), and had an illustrious career in the U.S. Coast Guard during World War II. hunting submarines before being refitted as a fishing schooner, and then, finally, lovingly reclaimed as a windjammer for passenger cruises.

Crew and passengers of the Nathaniel Bowditch work together to raise the sails (Copyright 2005 Karen Rubin).

Those of us who would dream of a chance to sail such a vessel get their wish-hoisting sails (even with eight on each the line, it is harder than you think), and hauling up the 400 pound anchor with an iron crank. Several of us take turns at the helm, learning how to watch the compass and point the bow, and getting that feeling of steering such a big, powerful ship under sail. We watch in amazement as crewmembers Chris or Tim climb the ladders to the top of the mast to attach a line.

Participation is encouraged, but not mandatory. Since the mainsail weighs 1,200 lbs., “the more hands the merrier.” We are 20 passengers on this voyage and we really do contribute a lot and I wonder how the crew of six manages when the Bowditch goes out with many fewer than the 24 passengers it carries. “With fewer people, there is more work, more profanity,” deckhand Lauren jokes.

We quickly learn the language and the rhythm of the commands: “2-6, heave; 2-6 heave,” and “Ready on the peak,” “Ready on the throat”.

We start out as strangers, but very quickly become companions. That is very probably because of the “heave to” that we do in teams-and because there are few distractions so that we each become a source of curiosity and interest to each other.

The Windjammer experience is as much about the people-the personality of the captain, the crew, and the passengers-and the interplay with the ship that has its own persona. All of these combine into a serendipitous experience.

We are lucky again-we have such a great group of people, who hail from all over the country-Ohio, upstate New York, Massachusetts, Maryland, and even London–and with very different backgrounds.

Most of us are in our 50s to 60s, but one couple has brought their teenage daughter (who celebrates her 16th birthday during our trip) and her friend. I can see how this would be a great experience for an extended family or a family reunion; in fact, some of the windjammers can be taken over by a group. Some of the ships (like the Isaac Evans and the Nathaniel Hawthorne) even encourage families and children as young as eight. Capt. Owen, in fact, has a three-year old son, Spencer, who will likely be on some of the voyages this season-very probably the trips that cater to families.

Captain Owen Dorr of the windjammer Nathaniel Bowditch gives advice on steering the ship(Copyright 2005 Karen Rubin).

Like the ship he now owns and commands, which was built nearby in East Boothbay, Capt. Owen Dorr is a native Mainer with a forthright manner and a droll sense of humor. He is passionate about sailing and had served as crew and first mate on windjammers for 20 years before taking the plunge and purchasing the Nathaniel Bowditch.

The people like Captain Owen and his wife, Cathie, who take over such ships, do it not just because they have a passion for sailing and life on the water; they recognize their responsibility as a caretaker of these proud ships. They adopt it. “We are the caretakers,” says Capt. Owen. “Our mission is to leave her better than we found her.” That is what Capt. Owen intends.

Each morning, we are lulled from sleep and lured from our cabins by the aroma of freshly baked muffins or scones-absolutely delectable-and coffee, followed by a sit-down breakfast served in the galley–of quiche or pancakes or eggs.

Lunch is a hearty soup or chili, very fresh and full of vegetables or beans, with freshly baked bread still hot from the oven.

Desserts are memorable-like a strawberry rhubarb pie with an amazing piecrust, or, after an “Italian night” dinner of eggplant parmagian served with freshly baked foccocia, peach cobbler served with homemade vanilla ice cream we have just prepared by grinding the ice, milk and flavorings together in an antique ice cream maker.

Meg, the cook (as well as deckhand), admits to never having cooked before she took on the role on the ship-it is a skill she has acquired deliberately, like sailing. We are in disbelief because everything has been so scrumptious.

When we have enjoyed something in particular and ask her recipe-like the delectable and wholesome butternut squash soup she has whipped up for Monday’s lunch, with onions, garlic, cumin, curry, she simply refers us to her two “Bibles”: “The Joy of Cooking” and “How to Cook Everything.” She confides about some of the challenges-like how the humidity can be so severe, it causes the baked bread to fail. But she really has a knack. She actually raises her own herbs in the galley. (Since she gets up at 4:30 a.m. each day, quiet time on this ship starts at 9 p.m.)

Chris, just a high school senior this year (he loves drama and would be my pick to be discovered for Hollywood) is straight out of central casting of the “Hornblower” series–striking blue eyes, wavy blond hair, handsome, nimble, lean and wiry.

Lauren, self-described “galley goddess and “deckhand dog”, is a real sailor-her mother was a racer.

Tim is a geology student from Philadelphia, talks about how fabulous it is to crew, learning all new and varied skills.

Monday night, after our first full day of sailing, we pull into this little cove between two islands to anchor. Since they are privately owned, we are not allowed to go ashore. We spend some time taking out the rowboat and feel like we are exploring.

The next morning we get under sail and find ourselves in a veritable “minefield” of lobster pots as far as the eye could see. To our uninitiated eye, it looks like the lobstermen are too aggressive and could harvest the lobsters to extinction; later, we meet a local who raises similar concern.

Soon, we find we are tangled in a line–a serious matter, since it is the lobsterman’s livelihood on the line. Capt. Owen does his best to free us without interfering with the trap. Finally, a lobster boat-a father and son-come by and help free us from the two traps (one is theirs).

It’s a big deal-if would lose the pot would also lose a precious medallion-only 800 medallions are allocated to each licensed lobsterman, and they are hard to get.

Watching the lobsterman and his son, we come away with a better appreciation for how grueling the job is, especially in the cold, foul weather.

Lobster Bake

A lobster bake is one of the highlights of any Maine windjammer cruise, and was certainly a highlight of our trip on the Nathaniel Bowditch, anchored (Copyright 2005 Karen Rubin).

We are actually good business for the lobstermen.

The highlight of the voyage for all the windjammers in the Maine Windjammer fleet is a Lobster bake on an uninhabited island.

Capt. Owen watches the weather and decides that Tuesday, rather than Wednesday (the last night of our trip, which is when it is usually held), would be a better bet, so we sail for Stonington, a charming fishing village on Deer Isle to pick up a crate of freshly caught lobsters.

We spend a delightful hour and a half in Stonington while Capt. Owen does his shopping. He has recommended we visit the Purple Fish Shop on Main Street, where the proprietor will create a bookmark in watercolor of our ship.

Meeting Katherine Olson Kole is a highlight of our short visit and the trip overall. She is an artist and an art teacher, who in a matter of minutes, has painted in the inked outline she has prepared in advance of the Nathaniel Hawthorne, and personalizes it as a bookmark, all for $3.50. She is a wonderful artist, but describes herself as a writer of songs of Maine; her husband usually plays music on guitar as she paints and we wait (unfortunately, he is not there today). She regards her painting as a way of doing her part to preserve the windjammers-it is probably a symbiotic relationship. In fact, she is more than an artist and a writer of songs. She is a keeper of the Maine heritage.

“I like to do things for the boats-and for the people who are trying to keep these jewels of the sea alive.”

Artist Katherine Olson Kole paints a bookmark in the image of Nathaniel Bowditch as we wait in her shop in Stonington (Copyright 2005 Karen Rubin).

While she works on the bookmarks for the seven of us waiting out turn, we chat about life. She has opinions about the lobster pots that blanket certain areas more like pointillism than an occasional dot. “You could practically walk across the bay on the traps.”

She says, “They should have asked the fishermen’s wives when they decided how many permits to sell. They’ve given out too many,” she says. The wives worry that “If you put out twice as many traps, you will catch twice as many lobsters but will deplete the supply.” Apparently, Fishermen’s wives have their own organization. It’s that difference between the short view and the long view.

Leaving her shop, we stop in at the cute little boutiques; there is also the Deer Isle Granite Museum-a reminder that granite has been a big industry here-and stop at a cute little ice cream stand operated by a guy who used to hail from Brooklyn.

When we leave Stonington, the sky is clear and there is a brisk wind. We experience the feeling of heeling-when the ship leans over as it finds the fastest point of sail. We are flying along at about 8 knots, Capt. Owen says.

We sail through the afternoon and come to this amazing little island that has a natural harbor-rocks on either side of a flat sandy “ramp”.

We go ashore in rowboats-a few intrepid ones swim in the cold Maine water-while water is put up to boil over a campfire.

The lobsters boil and when they are finished, Captain Owen spreads them with a flourish, over a bed of kelp we have gathered out of the water. They are served with melted butter and ears of corn.

I have never tasted such sweet, tender lobster-the shells are so soft, you simply tear them with your fingers (the Captain has purposely acquired “shedders” which have soft shells and a very sweet flavor). There are so many, we could have two. Dessert, which completes this festive campout, is S’mores.

It is an idyllic setting with a perfect sunset and a memorable meal.

The campfire is fitting–a windjammer sailing trip is more like camping than a cruising.


Two of the Maine Windjammers sailing so gracefully into the Penobscot Bay.(Copyright 2005 Karen Rubin).

Sailing on a windjammer is more of a voyage than a cruise. It is the difference between being a spectator in life and being a participant. It is a special sort of experience that comes from being involved, being a part.

Windjamming is not for everybody-it is very much like camping on water. You are roughing it, but you learn how to do with simpler things and ultimately, enjoy a simple life-the whole notion of traveling by wind, tide and whim. But sailing is not simple, at all; you come away with enormous respect for the skills and physical agility and quick-thinking that is involved.

I must confess that I am not a sailor; I am prone to seasickness. And I don’t like to be sedentary. Yet, I love this experience on the Nathaniel Bowditch-for me, it is a photographer’s dream; I am never seasick and never bored. There is always some interesting scene to frame, some thought to be written in my journal, some conversation to jump in.

Without a barrage of distractions, you would be amazed at how simple things capture your attention and become important, or how you find yourself really focusing on other people-your spouse, your child, or the new friends you are sailing with.

Rustic Digs

Our cabin on the Nathaniel Bowditch windjammer-a historic ship that was originally built in 1922 as a racing yacht and converted to passenger use in the 1970s–is very small and very basic-a bunk bed with wooden slates. The cabin is so small that two people can’t dress at the same time; there are no closets or even a bureau, just a couple of cubbies and hooks-you stow your bag under the bunk (ours had two single bunks but some cabins have a double).

There are glass-filled slats that let light into the cabin-air comes in from the top of the door, and the hatch is just above, so even though the cabin is tiny, you don’t feel shut in or nauseas. At night, a canvass covers the front of the ship, so rain doesn’t come in.

The galley is surprisingly light and airy with beautiful wood paneling and a fabulous cast iron stove as old as the ship. The galley also serves as the cabin for the crew. It has a hatch with glass, and windows and is comfortable to sit in. Many of our meals, though, are eaten on deck. We all pitch in to wash the dishes-a two-dip bucket system with salt water soaping, then fresh water with bleach rinse-that saves water.

There is water and electricity. As Capt. Owen says, “We have plenty to use and none to waste.” He points out that the engine can make electricity but it is noisy and he doesn’t want to operate it unless it is needed; if we use up our supply of water, we have to go in for more.

There are no showers on the Bowditch; a few passengers (and crew) braved the chilly Maine water for a swim and Joy shampoo, but warm rinses can be arranged if the stove has been on. More importantly, there is a “head” that is just outside our cabin and that flushes reliably.

We sleep on board Sunday night, in preparation for our departure on Monday at about 10:30 a.m. We had traveled in by plane during the day-a nine or 10-hour trip cut to a reasonable four hours or so by USAir and Colgan Air, including the change in Boston and a brief stop in Augusta.

Since we have some time after breakfast Monday morning before we leave, I wander from our pier along a beautiful walkway to Rockland’s Main Street to pick up some supplies at the CVS just above the harbor (insect spray and itch medicine; soda and snacks, AA batteries which I find my digital camera consumes at prodigious rates.)

I stop in at the Rockland Post Office on Limerock Avenue and discover that it has an amazing collection of Presidential citations going back to Grant in 1869, through Coolidge, Theodore Roosevelt, William Buckley, Cleveland, Harrison, Hayes.

In fact, Rockland, which gets more and more charming each time I visit, has just celebrated the 150th anniversary of its founding in 1854 as Lime City (Farnsworth, for which the museum is named, made his money selling the lime).

The Farnsworth Museum is world-famous for its extraordinary collection of Wyeths. Indeed, the Wyeths have a close connection to Rockland-the farm where Andrew painted some of his most famous paintings is nearby; his wife, Betsy, is a founding member of the Island Institute, headquartered on Rockland’s main street, dedicated to preserving islands. The day of our return from our windjammer trip, I visit the Farnsworth Museum and happen upon Andrew Wyeth’s granddaughter leading a tour to describe the “backstage” stories of his paintings. Just another example of the serendipity that makes this whole saga so memorable.

I make sure I am back on board with plenty of time to spare as we make ready to get underway. Captain Owen Dorr invites us to help raise the sails and teaches us the commands: “Haul away.” “Hold that line.” “Drop that line.” Then: “Ready on the peak.” “Hold peak.” “Ready on the throat.” “2-6-heave”

It is so magnificent as we sail out of Rockland harbor-like a collective breath of fresh air and the tingle of the unknown that lay ahead. We pass the breakwater that stretches out from the fabulous Samoset Resort (famous for its golf course) to the Rockland Light at its end, passed the Owl’s Head Lighthouse, where three other windjammers, their sails billowing, make a stunningly picturesque scene passing by as we make our way into the Penobscot Bay (Schooner captains talk to one another, letting each other where the wind is good.)

The waters are calmer here in Penobscot Bay than if we were sailing in the Atlantic Ocean-important because you are very unlikely to get seasick. Also, you sail amid thousands of small islands-which also break the “chop.” It also means you are always within sight of something interesting, so picturesque that I am constantly shooting pictures. I can see why this seascape has been so inspiring for so many painters.

During one stretch of smooth sailing, Capt. Owen pulls out a book that describes the history of the Nathaniel Bowditch.

The historic windjammer Nathaniel Bowditch at sunset, anchored for the evening (Copyright 2005 Karen Rubin).

Originally called Ladonna, the ship was built in 1922 as a racing yacht for Boston lawyer Homer Loving. It was designed by William Hand (who also designed another of the windjammers in the fleet, the Bowdoin) along the lines of a fishing schooner; both ships were built by the Hodgdon Brothers in nearby East Boothbay, Maine. Ladonna won honors for its class in the 1923 Bermuda Race. Then it was sold to a yachtsman in the New York Yacht Club and renamed the Jane Dore.

In World War II, the ship was requisitioned by the Navy to serve on submarine patrol. After the war, a fisherman bought it, took out the masts and installed a wheelhouse and used it to crag Long Island Sound for groundfish. The ship got plain worn out, and was left tied on pilings at Stonington. Connecticut. Then, in the early 1960s, its distinctive spoon bow caught the attention of Bob Douglas, who appreciated its “aristocratic” look, even in the sorry shape it was in. Douglas restored the ship, even scrounging around to find her masts, then sold it to Skip Hawkins who renamed it Joseph W. Hawkins, and took it to Stonington, Maine, to be fitted.

The ship was sold again in 1971 to a descendent of Nathaniel Bowditch (the author of the classic work on navigation, a Salem merchant, and one of America’s first millionaires) and a partner, who rebuilt it and renamed it the Nathaniel Bowditch. Finally, it was bought by Capt. Gil Philbrick and his wife who turned it into a windjammer for passenger cruises. Just a couple of years ago, Capt. Owen Dorr acquired it from the Philbricks.

Capt. Owen repeats was Capt. Philbrick used to say, and what has become his own mantra: “You never really own these historic vessels. You pass your time and try to leave them in better shape than you found them.”

We get a real sense of history as we come through a narrow channel into Popit Harbor on North Haven. There is a giant osprey nest that has actually been on the navigation charts from the 1800s. The nest, now absolutely enormous, is still there after all these years.

It isn’t always smooth sailing. The ship had gotten caught up in the lobster lines on our first day, now, as we are trying to raise the anchor-a true antique, 400 lbs. that is manually hauled up by a chain-we find that it is tangled up in a lobster line, and coming up so that it is “crowning” (coming up upside down which is as serious as a breech birth). This becomes a matter of significant urgency, and we all try to help with the cranking and holding the lines.

The commands and responses commence with a discipline worthy of the Navy. “Standing by.” “Aye.” “2-6 heave.” “Hold.” “Ease away gently.” “All slack.” “Hold burton.” “Belay that.” “Belaid”

Dan, the first mate, stands on the anchor, trying to untangle the chain. The physical strength and dexterity in all these things is amazing, as is the rapid response and instinct to deal with the problem, which has become rather serious.

Then he begins a new series of commands, “2-6 heave.” “Haul it up burton.” “Make this quick.” “Ease your burton.” “Easing.” “Ease your burton.” “Easing.” “All slack.” “All slack.”

Dan, hanging off the side of the boat, has to attach a rope to the anchor, so with his free hand, ties a knot so that he can flip the anchor over.

Meg, who serves as the cook on this voyage, has come up from the galley to add her strength and skill; at the same time she is hauling line, she is giving directions to a passenger who has taken over the meal preparations, to get olive oil for the onions which are simmering on the galley stove.

“Get on that burton�lower,” “Aye.” “Ratchet up the chain.” “Hold.”

Those of us who are not cranking or hauling are all watching, silently, transfixed at the drama of trying to fix the anchor.

Dan uses an iron hook to try to grab the anchor in such a way as to bring it up straight.

“Taking strength.” “Taking strength.” “Haul away.”

The problem is to pull up the anchor so the hook doesn’t smash into the hull. Finally, he has positioned it and the anchor can be pulled up. “Ease Burton.” “All slack.”

The maneuver has taken 45 minutes. We are able to get underway.

Porpoises swim off the starboard, as we pick up speed.

The night before, two young girls have come by the ship pretending to be pirates and extracting a promise that we fire off a cannon the next morning. As we sail by their house, Capt. Owen orders that our cannon be fired.

We sail under Deer Isle Bridge-85 feet high, and the ship to the top mast is 85 feet. Tim quickly climbs the mast to drop the topmast so we just slip under bridge. We pass through Eggomoggin Reach.

I try to retrace where we have sailed on the navigation maps: from Rockland, through Fox Thoroughfare to Isle au Haut (where we docked the first night), then to Stonington on Deer Isle, through a patch of islands below Marshall Island and Swan Island, up the Jericho thoroughfare; we docked at Bear Island for our lobster bake, then through Eggomoggin Bridge.

So far, we have sailed almost to Mount Desert Island where Bar Harbor is, which is the destination for the longer, six to seven day trips, to Summit Sound (the only fjord in the U.S.) and Frenchman’s Bay.

If we would have driven from Rockland to Bar Harbor, it would have taken three hours-instead of three days.

Our last night is spent at Vinal Haven, a crowded cove of incredibly posh ships.

As we are sailing back to Rockland, all of a sudden we hit a patch of fog like a wall. One moment, it is clear sailing, the next, a deep, dank fog and the air has become cold and damp, adding drama (and dimension) to our last hours of our voyage.

Every two minutes, Tim, a deckhand from Philadelphia where he is a graduate student, sitting on the bow, blows a fog horn: one long (five seconds) and two short (two seconds each), telling anyone who might be in that soup that we are a ship under sail, with limited maneuverability is coming, and have right of way.

A ship suddenly bursts out of the fog, giving one long blast-a signal it is under motor. “Boat to starboard,” Tim calls out.

Lauren, who has been such a chipper crewmember, entertains some of us with a knot puzzle to figure out.

Then, almost as suddenly as it had appeared, the fog clears and the sun returns, just as bell rings for lunch: freshly baked dill bread, still warm from the oven; tortellini soup with vegetables in thick chicken broth.

Finally, we spot the Rockland Lighthouse. As we come into Rockland, Capt. Owen says, “That’s Indian for �hot showers.'” (In fact, the Chamber has pay showers available for boaters at the dock.)

As we pose for a picture before we depart the ship and part for our separate ways Captain Owen jokes, “On the first night, you were talking to each other like it was Thursday [the last day].”

Check the Nathaniel Hawthorne website ( for a sailing schedule and rates for 2005 season, which runs May 27-Oct. 10. Two and three-day sails start at $330; four-day sails start at $525; six day sails from $825. Some of the trips are themed, such as a July 9-12, Aug. 7-10 and 10-13, three-day “Kids and Family trip” at $505. Other specialty trips are for the Great Schooner Race, whale watching and music fest.

Getting to the ship was easy: we flew on US Air to Boston and then connected with Colgan Air (a US Air partner) to Rockland Airport, just a short drive from the pier. For those who drive, there is complimentary parking.

If you can, visit the Owl’s Head Transportation Museum (very close to the Airport), with an incredible collection of antique cars and airplanes, and the Owl’s Head Lighthouse, as well as the Farnsworth Museum (andOlson House, where the painting, Christina’s World. was set; see,Farnsworth Homestead, and the Shore Village Museum (Maine’s Lighthouse Museum) in Rockland.

If you want to stay over in Rockland before or after the cruise, you might try the LimeRock Inn, 96 LimeRock Street, Rockland, ME 04841, 800-LIMEROCK,

Capt. Owen & Cathie Dorr, 4 Gay Place, Rockland, ME 04841, 207-596-0401, 800-288-4098,,

The Nathaniel Bowditch is one of 14 in the Maine Windjammers Association fleet. For more information on programs, call 800-807 WIND or

For visitor information, contact, the Rockland-Thomaston Chamber of Commerce, Harbor Park, Rockland, ME 04841, 800-562-2529 or 207-596-0376,, email:
© 2005 Travel Features Syndicate, a division of Workstyles, Inc. All rights reserved. Send comments or travel questions to

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Karen Rubin is an eclectic travel writer who has been spanning the globe for more than 30 years reporting on interesting, intriguing people and places to explore for magazines, newspapers and online. She publishes Travel Features Syndicate in newspapers and online including, Huffington Post and and blogs at "Travel is a life-changing and an interactive experience that mutually benefits travelers and community." Contact Karen at 'Like' us at

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