Family Charter Downeast


Experienced dinghy sailors take a week off to explore the Maine coast and the wonders of Penobscot Bay  (published March 2017)

My family has sailed a lot of miles and, while that includes several cruises, the majority of our time is spent on Midwestern lakes racing on course circles. We longed for a new adventure and Maine’s Penobscot Bay beckoned.

Andy and I, with our daughters Avery and Jordan, picked up our charter boat, a 37 foot Dufour, in Manset (Southwest Harbor) on Maine’s Mount Desert Island. Northpoint Yacht Charters brokered the deal but the finer points of the arrangement were between us and the boat’s owner, Maria. She summed up, “The boat is old and so am I so please treat it that way.” Andy and I thought that a fair assessment as we set off for a loop around Penobscot Bay.

   We opted to reach up Blue Hill Bay on our first afternoon so that we could learn how the 35-year-old Heista handled and the forgiving reach allowed room and opportunity to conquer lobster-pot navigation. Multi-line traps use a buoy with a toggle attached by 15-foot warp, which allows the toggle to move with the tide. So, as the pot below catches one of Maine’s largest agriculture crops, the connecting line just below the water’s surface is perfectly poised to catch rudders, keels and props. Once we got the hang of the buoys’ movements, the obstacle course that blankets the bay was not difficult to navigate.

Pretty Marsh Harbor on the western side of Mount Desert Island was the first night’s host. The anchorage was easy, the lobster buoys few, and a small finger of Arcadia Park that stretches over from Bar Harbor provided a destination for exploring ashore.

The first time out in the Dyer dinghy proved a challenge for my Ohio girls. In the land of rivers and lakes, we don’t row so much as we paddle. About halfway to shore, Avery and Jordan gave up rowing, each grabbed an oar and paddled canoe style the rest of the way. From Hestia’s cockpit, Andy and I enjoyed a glass of wine, laughed at their progress and hoped no New Englander eyes were judging.

Dawn brought light to moderate winds and a crew eager to see the sights so we beat southward through Blue Hill Bay, passing picturesque lighthouses along the way, to Eggemoggin Reach.


Our first stop was Center Harbor, which lies near the northeastern entrance of the reach. Sentinel seals sunned themselves on sloped granite rocks that mark the entry to the harbor. The famed Wooden Boat School and magazine make this their home here so it is well worth the stop. The grounds, school and mansion that houses the magazine are impressive. Although classes were not in session, we were welcomed to wander inside the school and admire the beautifully inlayed and varnished kayaks. The school’s large, grassy camping area was empty but the bay was quickly filling with rendezvous boats so after a couple of hours ashore, we opted to seek a more solitary spot for the night.

A friend had recommended Benjamin River which was about a mile east. One might be hard-pressed to find a more protected harbor but the plethora of lobster boats, mud flats and unsavory smell of the sea was not on our vacation wish list. As the day was growing long, we opted to spend the night at Thompson Cove directly across the river’s mouth.

The third time was indeed the charm as we had Thompson Cove to ourselves and a marvelous view of the Narrows Bridge back-lit by the setting sun. It also turned out to be the best wildlife anchorage of the week. An eagle pair nested in the tree line, harbor porpoises circled the boat so close we could hear them breathing and seals regularly popped their heads out of the water to check us out. I have not heard a loons’ call in many years and, as the sun set, their serenade capped off a beautiful evening.

The most difficult thing about Penobscot Bay is choosing between so many delightful destinations. One could easily spend a summer but we only had a week. Bucks Harbor summoned and Eggemoggin with the abandoned lighthouse looked idyllic but we sailed by and up Islesboro Harbor to historic Castine. Light and variable winds though Eggemoggin Reach forced the sails and the motor to take turns powering Hestia but our home winds on Cowan Lake, Ohio are fickle so furling and unfurling the sails left the crew unfazed.


   First settled in 1629, Castine is one of the oldest settlements in the country and rich in history. During the Revolutionary War, the Americans, being chased by a large British fleet, were unable to enter Castine Harbor and rather than have the British capture the fleet, they burned their boats as they retreated. As many as 500 Americans lost their lives in the expedition. Paul Revere was a leader of the mission and was both court marshalled and later acquitted for the disaster. The locals, who understand the lay of the land, water and tides maintain that Revere absolutely made the right decision.

We picked up a mooring ball off Eaton’s Boatyard but were drawn to the Castine Yacht Club’s hot showers next door. It didn’t take long to strike up a conversation with a fellow who began with, “Today I am the launch driver.” After few minutes we discovered that Mike Coughlin was also charming, the club’s commodore and a wealth of information. He noted that the club is making an effort to welcome cruisers and given the opportunity, one should hookup to a CYC mooring ball. The amiable Castine Yacht Club is a sailors’ haven with floats full of Optis, 420s and coaching boats. Adults race gorgeous wooden Castine Dinghies, which we admired with great envy.

    With Fort George a few blocks from the heart of town and the Dice Head Lighthouse a mile beyond that, Castine offers much to explore. Numerous art studios, historic markers and blooming gardens made for an enjoyable afternoon walk. Children, with life-jackets slung over their shoulders, passed us on bikes signaling that sailing lessons were over for the day. We agreed that any town where children simultaneously ride bicycles and wear life jackets must be among the best places on earth.

Back in the heart of town, a fragrant garden drew our attention and as we were admiring the blooms, the door to the house opened, and Mike said, “So we meet again.” He insisted that people from Ohio come here the first time by boat and then come back to buy a house.

Dennett’s Wharf sports both a reputation for excellent lobster dinners and a large deck overlooking the Bagaduce River and Smith Cove. We needed no other convincing. After indulging in large plates of steamed lobster, we couldn’t help but overhear a foursome discussing street names from the neighborhood where Andy grew up near Columbus, OH. Naturally, we struck a conversation. “Oh yes,” said one of the couples, “We sailed here first, but then came back for a house.” I confess, that Andy and I have checked Castine Real Estate listings more than once.


   On Mike’s recommendation, we set course to North Haven’s Pulpit Harbor. In the middle of the entrance to Pulpit Harbor a large rock hosts a 170 year old Osprey nest and, true to the guide book, an osprey obligingly sat on an enormous pile of sticks.

The protected harbor was chock-a-block full with cruising boats and local boats on mooring balls. Some balls might have been available, but we were unsure which so dropped anchor. As the afternoon sun began to cast shadows we rigged the sail on the Dyer dinghy and took turns discovering the harbor. Avery and Jordan sail much better than they row.

A lobsterman’s float near the mouth of the harbor attracted brisk business and when a neighboring sailor offered a ride over, I could not resist. Lobster plucked from a floating crate at $5 a pound made the crew smile.

Pulpit Harbor lies on the western side of North Haven Island and the sun setting over the Camden Hills is a spectacular sight. Dining on fresh lobster accompanied by a lovely pinot grigio as the sky turned orange and pink was a trip highlight. A couple who had dropped anchor while under sail earlier had gained our admiration and later one of their crew brought out his guitar and sent a few soft chords drifting over the harbor. Perfect.

   From Pulpit Harbor, we circled North Haven Island via the Fox Island Thorofare, which is a beautiful seven-mile stretch between the islands of Vinalhaven and North Haven. The eastern entrance is marked by a granite stone and the 150 year old Browns Head Light. Depending on the width of the thorofare, we sailed or motored all the while admiring amazing homes.

The town of North Haven lies at about the midpoint through the thorofare and was the last town we would see on our loop cruise. North Haven has a few eateries including the beautiful Calderwood Inn, which in addition to the restaurant, has a gourmet grocery store that offers two food groups that matter most: fresh bread and ice cream.

The eastern end of the thorofare widens and the wind piped up to 15-to-20 knots where it remained for the rest of the week. Several classic schooners sailed close by as we made our way toward Seal Bay where one could spend days exploring a multitude of inlets and islands.

We thought we’d find shelter from ocean breezes by anchoring deep into the bay so we dropped the hook between Burnt and Penobscot Islands. However, the wind funneled between them and Penobscot Island is private so while very close, did not extend an invitation. We pulled up anchor and snuggled in closer to Hen Island with the Bluff Islands off the transom. A short run, sans sail, offered our budding naturalists an opportunity to stretch their legs.

Two children are proof there is more than one way to explore. Avery neatly explored the shoreline while Jordan took a more hands-on approach. Or rather more hands, arms, legs and feet-on approach and was soon covered in black mud. Papa took one look at his younger daughter and let out a Whisky Tango Foxtrox growl. Before climbing back aboard our boat, Jordan took a chilly Penobscot Bay swim.


Whale watching at Matinicus Rock was high on the pre-trip priority list. The guide books assured that once offshore we’d leave land behind but on this blue-sky day, the island dotted the horizon. It was tantalizingly close, but the boat was old and slow and we were not fully acquainted with her seaworthiness so we opted to reach across Isle au Haut Bay.

The high mountain that rises 556 feet out of the sea is impressive and the town below is don’t-blink tiny. This part of Arcadia National Park is remote and the thorofare funnels ocean winds. The sailboat that entered the narrow passage ahead of us snapped up the last mooring ball and, while anchoring is doable, viable spots are few. Two nights on a windy hook near a rocky shore had Andy less than enthused so with eagles soaring overhead, we sailed out the northern end to the Merchant Row archipelago.

   Merchant Row islands are set off with pink granite and while most are private, four are park land. Despite having grown accustomed Penobscot Bay’s three million plus lobster traps, the number of buoys around Merchant Row was amazing and we had to carefully navigate our way to the sheltered northern side of McGlathery Island. It was worth the effort.

McClathery’s protected harbor, tidal pools and trails are some of the prettiest in Penobscot Bay. The trail that winds across the island is well marked with pieces of lobster buoys. It struck us that everyone who ran afoul of a trap saved the foam bits then pierced them on a tree branch in an act of collective revenge. The windward side of the island revealed an expansive beach and swift tidal channel. On the harbor side, no-name island connects to McGlathrey and at low tide it is easy to simply wandered over. I was lucky enough to enjoy the magic of having an entire island to myself for a short while.


One of the best sails of the week had us crossing Jericho Bay back home to Manset. With the wind blowing 20 knots, Heista scooted along nicely and we never tired of looking at schooners, seals and lighthouses.

On shore a free bus, which snakes around Desert Island, carried us the two miles between Manset and Southwest Harbor. Southwest Harbor is billed as a working town but we found plenty of interesting restaurants and shops. Charlotte’s Lobster Pound is a throwback place where you eat lobster rolls in Adirondack chairs then hula hoop with your newly met friends. We made the obligatory visit to Bar Harbor on the other side of Mount Desert Island but found Southwest Harbor more authentic and less crowded.

Manset is the original home to the famed Hinckley Yachts and you’d be hard pressed to find a nicer yard crew. We topped off the fuel and water before returning the boat and the free showers pleased the crew. Next door, Charlotte’s Satellite Shack offered a hearty breakfast of eggs, pancakes and hot coffee. By then we knew Charlotte well enough to hug good-bye.

  Happily, we discovered that the girls’ dinghy sailing skills easily transitioned to a larger vessel and that the four of us make a good cruising crew. Plus, we learned more about what equipment we’d want on a bigger boat (when the time comes), and that we’d like to continue to expand our sailing circles. Who knows where next? Maybe somewhere warm.

Patty Lawrence is former US Sailing board member and a past president of the Thistle Class Association. When she is not on the water, Patty enjoys teaching sailing and organizing the seminars for Strictly Sail Chicago and Miami.

Author: Patty Lawrence


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