SUMMER SAILING 2021: A Tale of Two Cruises


Sept. 2/2021:  The majority of my summer cruising in Maine this year, aside from some brief solo forays into Casco Bay, has been conducted in Penobscot Bay. All things considered, it is pretty much my favorite place on the coast. Given the prevailing conditions this season–light winds, fair doses of fog, and the odd hurricane threat–it has offered lots of interesting destinations not far removed from one another, at various sailing angles, good friends to visit with, and easy-to-access holes to hide in if necessary.

I had two good solid doses, two weeks each, in July and August, with two different crew. Victim 1 was Nat Smith, seen in the photo up top, helming Lunacy on a downwind wing-and-wing set, from Monhegan, an offshore island, all the way up to Belfast, at the top of the western side of Penobscot Bay, a distance of some 50 miles. It was one of the few times all summer, July 16, that I had a full day of solid wind, and I was determined to make the most of it. It ended in a fierce thunder squall, with gusts to 30 knots, late that afternoon as we entered Belfast Bay.

I first sailed with Nat in the spring of 2018, when he was first considering buying a Boréal like mine and talked me into taking him along on a coastal delivery leg from Jacksonville, Florida, to Morehead City, North Carolina. He in fact was good company and I was happy to have him aboard again. He has now actually ordered a Boréal of his own, so he was even more eager than before to learn all he could about Lunacy.

Journey to the center of my boat. Nat down in the deepest bilge sump, unraveling Boréalan mysteries


Inspecting my Windpilot windvane. Nat has actually ordered one of the new Boréal 47.2s, which have flat fold-down transoms, and he is pondering how such a vane might be installed on his boat


Victim 2, of course, was my lovely wife Clare, who joined me in August while the precocious daughter Lucy was imprisoned at her Performing Arts Stalag.

Clare looks a bit worried as we approach Bucksport on my very first foray ever up the Penobscot River. That fabulous bridge there, which opened in 2006, has an observation lounge at the top of its left-side suspension tower…


So of course we had to go there. It took a Forced Hunger March of about three miles and a slow but very smooth elevator ride, but finally we made it. Here we see Bucksport from on high, with Lunacy in the river second from the right, and Fort Knox, across the river from the town, on the left


River level view. You see Fort Knox now on the right, with the bridge tower (crowned with its observation lounge) on the left. Bucksport in fact is about 10 miles inland from the top of Penobscot Bay. We sailed most of the way there from Castine, on a moderate easterly wind generated by Tropical Storm Henri, which was then coming ashore in distant Rhode Island


This is just a smattering of the many boats that came to hide from Henri in Smith Cove, just south of Castine, while Clare and I were en route to Bucksport. The forecast here was for gusts to 20 knots, which I guess some people find pretty scary


During my previous visit to Castine, in July with Nat, we were surprised to find a replica of Columbus’s flagship Santa Maria in residence


Which of course we had to board and inspect. Afterwards we went on a Forced Hunger March, searching for the Castine summer home where Nat’s mom once worked as a nanny many decades earlier. We did not find it, but we think we did come close


Nat and I had sailed from Belfast to Castine on a rainy day in a baffling light easterly that later firmed up and veered into the northeast. In all it took us about three hours to cover a distance of seven miles


This is the secret to light-air cruising. Patience. A willingness to go wherever the wind will take you. And a willingness to do some (often pointless) sailhandling. Here I am en route solo from Portland to Rockland during the August cruise, during which I launched and struck the A-sail a few times over two days


While in Belfast Nat and I visited with Emily Greenberg, who was still there commissioning Teal, the Tripp 29 I helped her buy earlier in the year. The last job she needed to do before finally leaving was to refurbish and reinstall her Hydrovane steering gear. Here I am helping her reassemble the vane with some new parts she had machined at a local shop


And here’s Nat helping her bolt the vane back on to Teal’s transom. Soon afterwards Emily escaped from Belfast, and Clare and I ran into her later in Rockland, where Emily trapped me into a scandalous podcast interview


One unique very cool feature in Belfast is this mast-stepping barge, originally designed by William Atkins. Emily used this to unstep and restep her mast so she could thoroughly inspect it and replace some masthead sheaves and running rigging


Clare and I in fact started our August cruise in Rockland, where I met her on Lunacy after she dropped Lucy off at the stalag. While provisioning there, I made an amazing discovery: a pale summer ale named after Popham Beach, the emotional epicenter of my life on the Maine coast, brewed by a company named after my dog. I guess this means I can now die and go to heaven


From Rockland Clare and I sailed, again very slowly, in tricky light air, across West Penobscot Bay and through the Fox Island Thorofare between North Haven and Vinalhaven. We landed at Calderwood Island, at the thorofare’s east entrance, keeping company with a very cool 1965 Hinckley Pilot yawl with a fresh carbon-fiber rig


Calderwood reminded me a bit of Holbrook Island, just south of Castine, which I visited earlier with Nat. Both islands have excellent hiking trails and a fair amount of open space


When I was in Rockland with Nat we visited with my old friend Loric Weymouth, of Weymouth Yacht Rigging (left), who took us out for a spin around the harbor aboard his vintage Lyman runabout Dog Watch. Loric graciously let Nat do the driving


While in Camden we also visited with Ben Ellison, of Panbo fame (left), and his daughter Jesse, who took us out to haul a few lobster traps. They graciously let Nat and I keep the only two bugs they caught. When Clare and I visited with Ben again during our stop in Camden, he informed me he in fact has caught very few lobsters this season


From Calderwood Island Clare and I puttered a short distance to Stonington, at the south end of Deer Isle. I hadn’t visited here since the 1990s, when I stopped in on my old yawl Crazy Horse and was put off by how unfriendly the large fishing community was. If you study the user comments on the Navionics app, you’ll find fairly recent accounts of lobstermen actively harassing sailboats in the area. Word now, however, is that Stonington is friendlier than it used to be. That may be the case. On our way in we “rescued” a fisherman in a skiff whose outboard had quit (i.e., we gave him a tow to the nearest dock), and perhaps word of our good deed spread on the waterfront. At least no one hassled us. On shore we found more businesses oriented toward tourists than I remembered, but still there were a few no-nonsense storefronts on the main drag, like this one here


From Stonington Clare and I sailed out the Deer Isle Thorofare on a boisterous easterly breeze (the first hint of Henri’s advent) and all the way up the east side of Penobscot Bay to Castine. Here’s Clare studying the cruising guide as we ease past Eagle Island


While approaching Castine I spotted this craft from a distance. Winner of this year’s Unidentified Sailing Object (USO) award. (I’ve always been interested in junk rigs, but have never had a chance to try sailing with one)


This was our top Identified Sailing Object, the schooner Victory Chimes, which sailed by close aboard as Nat and I finally ghosted our way out of Penobscot Bay


On our way back to Portland Nat and I stopped first at Maple Juice Cove, in Cushing, a short distance up the St. Georges River. Again, I hadn’t visited here by boat since the ‘90s. It is the sight of the Olson house, prominently featured in the famous Andrew Wyeth painting Christina’s World. We went ashore to check it out (the house now belongs to the Farnsworth Museum in Rockland) and found this tiny graveyard at the foot of the pasture that leads up to the house. Many Olsons are buried here, including Christina


And also the artist himself, and his wife Betsy


We also stopped at Popham Beach, where we dried out the boat for an evening and visited with my old friend Kurt Meinen and his dog Percy. That’s the front of Fort Popham on the left and my grandmother’s old house, where my mom was raised, on the headland to the right


And again at Jewell Island, not far from Portland, where we checked out the old WWII observation towers


The last stop on my August cruise with Clare, before we returned to Rockland together, was at Hurricane Island, which I hadn’t visited in decades. This is Clare inspecting the quarry at the island’s south end. Last I was here that granite wall had Outward Bound students on it, clinging eagerly to ropes. The island still hosts a very active program and guests are always welcome


After we hiked the island in the morning, Clare and I had lunch on our Hurricane Island mooring with Loric and his wife Jen, who jetted over from Rockland on Dog Watch


The same day Clare left the boat in Rockland to retrieve the precocious daughter from camp, I motored in no wind over this eerily molten sea out to Burnt Island (seen in the background here), way off the mouth of the St. Georges River. Spent an uneasy night anchored there, as the forecast light southerly wind turned out to be a moderate northeasterly wind, which put me on a lee shore. I heard my chain rode making angry noises all night and wondered if it was dragging. Turned out it was busy wrapping itself around some rocks as the wind shifted, and it took a while to get it free next morning


Fortunately, that northeast wind shifted to the south-southeast in the morning and gave me a fine ride on a light-to-moderate close reach all the way back to Portland, a distance of about 50 miles. Seen here is a piratey motorsailing ketch that passed me to leeward and also happened to anchor off Maine Yacht Center, right near where I parked Lunacy after my second cruise of the summer was complete


About that daughter I mentioned earlier. When Clare picked her up at camp, it turned out she wasn’t our daughter anymore. Influenced no doubt by her arty theater-camp friends, she had decided she was now instead our non-binary child, named Jay, with pronouns they, them, theirs.

So be prepared. Future references to my spawn in this blog may be confusing.

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5 Responses
    1. Charles Doane

      John: I had hoped to put up a link, but Emily hasn’t posted the podcast yet. It was pretty scandalous. I’ll put up separate post with a link to it once Emily puts it up on her site.

  1. Matt

    We actually passed by you on your way into Portland Harbor- was very cool seeing your hot in person. We were in our 22’ catboat Bonny (Marshall cat, gaff rig).

    Please keep up the writing I definitely enjoy the good reads! Thanks for the effort.

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