Sailing the Maine Coast

Share on

Frenchboro, Brooklin, Midcoast Maine, pink granite, lobster rolls, E.B. White, phosphorescence, Eggemoggin Reach, Deer Isle, Pulpit Harbor, Calderwood Hall, oyster martinis, line-caught halibut, The Harbor Gawker, skipjacks, puffins, Isle au Haut, Vinalhaven & Samuel de Champlain.

Photos by Sara Fox

Mount Desert Island

Green-blue water swirled around the dock. We loaded food, water, toolkits and charts onto the boat. It had rained for three days, but it was sunny today. There were no clouds. The entire Atlantic was a sun. The mountains of Mount Desert Island were shadowy silhouettes in the sky. It was late, almost 4 p.m. The tide was ebbing and there was a nice breeze, but there was no way we were going to get to our first harbor before dark.

My wife, Sara, handed me supplies through the companionway and I stashed them in the cabin. The boat was a thirty-two-foot cat ketch. It was both new and old to me. I was on this dock the day it was first launched, in the spring of 1981. My father and his crew built it in Southwest Harbor, a few miles away. The company was called Able Marine and the boats my father dreamed up were called Whistlers. They built twenty of them, between thirty and fifty feet long, in a shop in our backyard. Chuck Paine designed them. They became instant classics in what was a golden era of Maine boat building.

Many builders from that time have passed on, but some still build world-renowned yachts. My father died in 2004 at the age of sixty-two. I had been looking for one of his boats ever since and finally found one in 2015. It was the first Whistler ever built. It was stout and beautifully outfitted with a cherry interior and simple rig. I remember the night the hull arrived at the shop and the two years it took to build it.

Now my wife and I were taking Whistler I on a cruise down the coast I grew up on: ten days in Midcoast Maine, from Mount Desert Island through Jericho Bay to the southernmost tip of Penobscot Bay. We wanted to visit harbors that most tourists miss, find the smallest gunkholes and best sailor’s bars that no one has heard of. We wanted to drop off the map and feel our way down the longest coastline in America. So against all wisdom, with two hours of light left, we untied the dock lines, pushed off and headed out to sea.

[smartslider3 slider=12]


To get to open ocean in Maine, all you have to do is sail east. The state is shaped like a chicken’s head, with the ragged coastline running along the eastern edge. In a straight line, the coast is 293 miles. The actual tide-affected shoreline is 4,568 miles. Include the forty-six hundred islands and ledges scattered offshore and it grows to more than seven thousand miles—longer than the entire East Coast of the United States and three times California’s coastline.

We sailed through a cluster of forested islands surrounding Mount Desert Island. Samuel Champlain named M.D.I. on his maiden voyage to what he hoped would become New France. He was a master sailor and still managed to go aground off Otter Cliffs in 1604, near Bar Harbor. His crew hauled the boat ashore, waited for the tide to beach it, then patched the hole and continued on at high tide.

Maine’s actual tide-affected shoreline is 4,568 miles. Include the forty-six hundred islands and ledges scattered offshore and it grows to more than seven thousand miles—longer than the entire East Coast of the United States and three times California’s coastline.

I was very aware of the shoals on our first day. We passed Flynn’s and Bunker ledges, where I hunted eider ducks as a boy with my father. Then we pointed Whistler I due east past the shadow of Swan’s Island toward the little rocky hump of Long Island. The sails filled; the boat heeled over; the bow plunged into the swells. We hit six knots on a close-hauled reach. The engine was off. The water, fuel and propane tanks were full. Only the wind heaved the boat forward. We could have sailed to France right then if we wanted.

Frenchboro would do. The little hamlet sits on the northwest corner of Long Island. The first stars were out when we followed the ninety-foot schooner Mary Day into Lunt’s Harbor. Twilight lit up the tops of the pines onshore and made the water silver-gold. Fifty-two hundred square feet of canvas fluttered over the Mary Day. I could smell bait on the stern of a moored lobster boat and diesel fumes from another coming in. There were a few houses scattered in the hills and new cedar shingles on the 1845 one-room schoolhouse in downtown Frenchboro.

By the time we found a mooring, it was dark. There was no moon. It looked like someone spilled a saltshaker into the sky. We grilled salmon under the stars and chatted with a few other cruisers in the harbor. A couple from Annapolis and one from Center Harbor had arrived that day. We were all doing the same thing: cutting the cord with the mainland and heading out to sea.


W          e hiked Frenchboro’s coastal trail system the next morning (trail maps). Long Island is overshadowed by Acadia National Park, which covers most of M.D.I. Yet Long Island has more miles of coastal trails than Acadia—sixteen in total. We walked over pink granite slabs, rocky beaches, limestone bluffs and elevated wooden pathways spanning bogs and streams. A secluded beach and a half mile of pink granite at the end of the trail arced away to the west. Rocky slabs the size of school buses perched on top of one another as blue waves crashed into the beach and cool sea air blew onshore.

We walked back to town past heaps of tangled lobster buoys and stopped at Frenchboro’s main attraction: Lunt’s Dockside Deli (1987 Lunt Harbor, 207-334-2902). The Maine coast has been mired in an unofficial lobster-roll war for decades. Sara and I have tried most of them, and there was no question that Lunt’s is king. Light mayo, capers, sweet and salty lobster right off the boat—on a buttered and browned hotdog bun. It was sunny again and seventy degrees. It was a perfect Maine moment, and a half hour later we sailed east to find another.

Maine’s version of Brooklyn is spelled Brooklin. By water, it is five miles west of M.D.I.; by land, it is forty-seven. The village has become a haven for writers and artists. One of the first was E.B. White, who moved to Brooklin in 1938 and wrote about life there for nearly fifty years. His son, Joel White, became a noted naval architect and started the Brooklin Boat Yard. Joel’s son, Steve, runs the yard now and came up through the Maine boat-building ranks with my father.

[smartslider3 slider=13]

Heavy winds knocked us around all day on our way there. We headed out around Swan’s Island to avoid the current, then turned back in to avoid heavy wind. The Gulf of Maine is one of the stormiest bodies of water in the world. It is a seiche, which means it is enclosed on all sides by land or underwater ridges. Storms hit and stay, warm water gives them energy and waves pound the shores every day.

We rounded Hat Island and set both sails for a four-hour broad reach through Jericho Bay. Whistler I yawed and surfed before the following sea. Sara made some food. I cracked a beer. When the sun started to fall behind Deer Isle and the wind finally died, we trimmed the sails and headed up Eggemoggin Reach.

The reach is a ten-mile runway of flat water that you can typically sail on one tack in both directions. It divides Deer Isle from the mainland and is one of the greatest sailing stretches on Earth. Whistler I sailed herself past the WoodenBoat School, set behind Babson Island, then around Torrey Islands and into Brooklin’s Center Harbor.

Classic yachts were stacked like matchsticks in the harbor. The hulls were sleek, mostly wood and varnished. It looked like a New Yorker cover set in an emerald-blue swimming pool. Steve White gave us a tour of the Brooklin Boat Yard (Center Harbor Road, 207-359-2236, the next morning. He had evolved the business from a classic wooden-boat shop to a contemporary, high-tech shipbuilding lab. His crew helped pioneer the modern era of “cold-molding” wooden boats and the space-age technique of building with carbon fiber composite.

Steve showed us a seventy-two-foot carbon fiber yacht being built for Spanish yacht designer Marcelino Botin. I watched a man spend twenty minutes fitting a perfect butt joint and others sanding and securing woodwork in the bow of the boat. A wooden steering wheel featuring the Brooklin Boatyard logo hung on the wall over the wood shop. Next spring, it will adorn the helm. The smells and sounds brought back memories of my father’s yard, and I told Steve about Whistler I. “I remember sailing that boat with your dad around the Miami boat show,” he said.

That night, we ate seared scallops, lobster salad and a Maine-raised rib-eye steak alongside a dozen octogenarians at the Brooklin Inn (22 Reach Road, 207-359-2777, Then we got a beer in the basement pub, where five local women told us they were from the tri-state area.

“Everyone walking through this town was either looking for it or got lost,” one of them said. “No one stumbles into Brooklin.”

“We all went through a hazing process,” said another. “It’s called winter.”

We were unhinged, a dot drifting on the sea. It wasn’t a familiar place. It felt like not being anywhere at all.

Phosphorescence filled the ocean that night as we drove the dinghy back to the boat. Yachts in the harbor were slender shadows between long runs of moonlight. We motored past Whistler I into Eggemoggin Reach, then drifted under the stars for a half hour. The sky was a blue-black sheet; satellites blinked overhead and a shooting star streaked toward us. There was no wind and the air smelled like saltwater and honeysuckle. We watched the scene silently, floating through space. We were unhinged, a dot drifting on the sea. It wasn’t a familiar place. It felt like not being anywhere at all.

Pickering Island

W          e pushed off at noon the next day. The wind was blowing down Eggemoggin Reach, and we followed it under the Deer Isle Bridge. Penobscot Bay lay on the other side. The massive sheet of water extends thirty-five miles inland from the Gulf and is twenty-seven miles at its widest. Working harbors like Rockland, Rockport, Stonington, Castine and Belfast sit around it. When Champlain first sailed into the bay, he wrote of the thickly forested landscape and “numerous islands, rocks, shoals, banks, and breakers on all sides, so that it is marvellous to behold.” Champlain had no maps and sailed with a lead line in his hand to feel for rocks. We navigated by compass and GPS past two schooners under full sail in the misty light.

We stopped for the night in a grouping of islands off Northwest Harbor. The islands were circled with granite, seaweed, exotic ducks and silvery seals. We anchored in Pickering Island’s Western Cove, between four beaches. Three were stone, one was sand. We lay in the sun on the sand beach and swam for a few hours. The water near the beaches was emerald blue like in the Caribbean. The air was eighty degrees and humid. We made food in the galley and ate in the cockpit with the warm sun coming down and a layer of cottony fog covering the Camden Hills ten miles to the east.

One hundred miles southwest was Portland and the white-sand beaches of southern Maine. A hundred northeast was the Canadian border. In between is what many sailors consider the greatest sailing grounds in the world.

We made a bonfire that night and ate dinner on the beach. The tide rushed out and left the dinghy high and dry. We lay on our backs and watched shooting stars. I had been reading about coastal Maine Indians and how they read the stars. Many saw their ancestors in the Milky Way, which they called the “ghost path” or the “path of souls.” That night the ghost path curved straight over Whistler I.

North Haven

The wind was howling the next morning, and we set up for what was going to be a rough day. Double reefs in both sails, winds gusting to thirty knots, seas four to six feet. The water was calm getting out of Pickering but got worse all day. I read the tide chart wrong and fought a two-knot current past Hardhead Island. A fifty-foot yawl in front of us almost got stuck near Butter Island and we did too, but we managed to round it and, four hours later, pull into Pulpit Harbor on North Haven.

[smartslider3 slider=14]

We picked up a mooring on the eastern end and ate lunch in peace, knowing that we were tied to a thousand-pound hunk of granite. Wind screamed through the rigging and blew the boat sideways. Streaks of fog whipped overhead at fifty miles an hour and a vintage WWII P-52 fighter plane from the Owls Head Transportation Museum cruised past.

That night, Amanda Hallowell picked us up and took us to the Nebo Lodge (11 Mullins Lane, 207-867-2007, for dinner. Amanda is the chef and general manager of the lodge. She treats guests like siblings she hasn’t seen in a while, dropping everything to get them a table, a glass of water, a ride to and from their boat. She and her sisters run the lodge and the Calderwood Hall restaurant (2 Iron Point Road, 207-867-4700, near the Fox Island Thoroughfare. Chellie Pingree owns and operates Nebo Lodge. She has also served Maine as a U.S. Representative since 2008.

We started our meal with an oyster martini—exactly what it sounds like—then moved on to line-caught halibut, fried green tomatoes and a dozen more oysters from the North Haven Oyster Company.

We started our meal with an oyster martini—exactly what it sounds like—then moved on to line-caught halibut, fried green tomatoes and a dozen more oysters from the North Haven Oyster Company (211 Middle Road, 207-867-4453,

The food was perfect, fresh from the ocean and nearby Turner Farm (138 Turner Farm Road, 207-867-2380,, which Pingree also owns. We sat at the bar with a few sailors, swapping stories; then Amanda handed us the keys to her truck and asked us to bring it back in the morning. We followed a Xeroxed map along windy asphalt roads back to the harbor. Wispy clouds streaked the night sky and a three-quarter moon hung just over the trees. There was fog in the harbor and we drove the dinghy blindly to Whistler I. Ghostly lobster boats and yachts slipped by as we puttered along. We eventually spotted the boat and pulled alongside.


The sun was out again and the weather was calm the next morning. We brought the truck to Calderwood Hall and drank strong coffee and ate egg sandwiches on homemade English muffins. A cool breeze blew through the whitewashed café—which has housed a dance hall, basketball court, movie theater, theater stage, diner, meeting hall and gift shop since it was built in 1908.

We headed out that afternoon, sailing west and south into a fifteen-knot wind. We could see two dozen giant windjammers parading through Rockland Harbor. Thunderstorms were expected, so we headed for an inlet on Green Island next to Vinalhaven. Vinalhaven is different from North Haven. Summer folks haven’t infiltrated it completely yet. Lobstermen outnumber tourists and they let you know your place when you arrive.

We squeezed between lobster boats with our dinghy on our way in and tied up to the town dock. The buildings on Main Street looked like they hadn’t changed in a century or so. We ate the best fish chowder of the trip at the Harbor Gawker (26 Main Street, 207-863-9365), along with a lobster roll and haddock sandwich. The Gawker has been a Vinalhaven mainstay for more than forty years. The floor and walls roll with the sea and the view of Carver’s Pond was so close it felt like we might fall into it.


Matinicus Island is the most remote inhabited island in Maine. We left at dawn the next morning to find it. Seas were calm near Green Island, but the moment we got offshore, five-foot swells rocked the boat. They didn’t stop until we pulled into Matinicus Harbor.

Most of the lobster boats were out and the dock was empty when we pulled in. A lobsterman on the pier said that the storm the night before had kicked up ten-foot waves in Penobscot Bay. A wave breaking over his bow nearly blew his windshield out.

There is no cell service on most parts of the island, so we called over the VHF radio to ask for lobsters. A lobsterman delivered four pound-and-a-halfers to our boat fifteen minutes later for twenty dollars.

We walked around Harbor Road past gardens, junkyards, cottages and a few thousand lobster traps stacked in neat rows. They used to build boats on the island, an old man working on his truck told us, a skipjack that won some races back in the day. But most people out there now fish. If you want to get to land quickly, an air taxi comes twice a day. There is no cell service on most parts of the island, so we called over the VHF radio to ask for lobsters. A lobsterman delivered four pound-and-a-halfers to our boat fifteen minutes later for twenty dollars.

[smartslider3 slider=15]

Sara made lobster salad as I steamed toward Seal Island to look for puffins. Puffins are one of the rarest birds in the Atlantic and some of them nest on Seal Island. The little black seabirds look like a mix between a black duck and a toucan, with bright red, yellow and white beaks. They are hilarious and aggressive little birds that fly at forty miles an hour and growl at anyone intruding on their turf.

We were the only boat at Seal Island that day and flights of two and three puffins soared past us all afternoon. Sara photographed them from the bow as I nudged Whistler I close to the rocky shore. After a couple of hours, we turned east again and headed for our last stop of the trip.

Isle au Haut

Acadia National Park covers most of Isle au Haut as well (trail maps). A few lobstermen live on the island year-round and their kids go to school there. There is one store and one paved road—fittingly named Main Road—that circles the island. We picked up a mooring, went ashore and set out on a hike in the park in fading golden light. The houses in town seemed to be from a children’s book written in the 1950s. They were tall and clapboard with cedar shingles. Most were sparsely filled with antique furniture.

The trees were sparse and from the top of the boulder pile I could see Penobscot Bay to the west and Jericho Bay wandering through a hundred islands to the east.

Champlain also named Isle au Haut, on his way to Penobscot Bay. It seemed appropriate that we end on his island, and his mountain. We hiked up the 540-vertical-foot Mount Champlain at sunset. The terrain looked exactly like Mount Desert Island. The red pine needles and pink granite showing through the soil reminded me of home. The trail wound uphill for almost a mile before petering out at a pile of boulders and a five-foot-long whale skull someone dragged up there. The trees were sparse and from the top of the boulder pile I could see Penobscot Bay to the west and Jericho Bay wandering through a hundred islands to the northeast.

[smartslider3 slider=16]

The sun set and we walked down slowly, following shafts of light that cut through the trees. We didn’t see another person the entire hike. Back at the dock, we untied the dinghy and puttered back to Whistler I. I learned to sail on this coast, but most of the trip had been new to me. Life is too short to explore every island and bay in Maine, and that is part of its allure. As we hauled up the sails the next morning and headed home, I was happy to know that the boat we were on had sailed the coast many times.

Sara and Porter Fox make Nowhere in Brooklyn, New York.

Share on

Submit a comment

Your email address will not be published. Required fields are marked *