Oct 19, 2021

Almost three weeks have gone by, and we’re now settled into our winter slip at DiMillo’s Marina on Commercial St. in downtown Portland. It’s been quite a transition from life at sea to life with one foot on land and one on the boat. Whereas previously we rowed our dinghy to get ashore from a mooring or anchor, now we step out of our boat onto a dock and drive the car when we need to get somewhere on land. It sure is different, we’re getting used to it, and so far so great! Here’s how we got here.

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The night we arrived back at our mooring, we got a text from a friend offering us her spot at a log cabin in a remote setting near Bethel, and we jumped at the chance. Two hours from Portland, this spot is an amazing oasis in the middle of 600 acres of woods with a pond, three houses, a 1902 log cabin that was moved from another location on the property, a sauna, and gardens. The creator of this compound is Jim, a Vietnam vet/engineer/back-to-the-lander who bought the property in the 70s and has lived there with his family ever since. His daughter now lives in the main house and rents the cabin on AirBnB ( while he occupies his time designing and building his son a round house that will hang above the tree line from a 30’ steel pole. In years past, Jim built Maine’s tallest snowman and snowwoman (; a hydroelectric dam that not only provided electricity to the property but put three kids through college back when the electric company still paid people for that sort of thing; a round house bermed into the hillside with a cement roof cast over snow; a tree house with a helix stair wrapping around the tree; and a mile long zip line that drapes above the pond. We so enjoyed hiking around the property looking for mushrooms, sitting in front of the woodstove, cooking tuna steaks with fresh peaches picked on the property and fresh eggs and herbs from the garden, and taking an icy dip in the pond after our sauna. Ah, Maine, the way life should be!

The glorious weather at the beginning of October sent us back out to Casco Bay, first to Jewell Island, where the first night we were there with just one other small sailboat. The walks ashore on Jewell are wonderful amidst the WWII cement relics that litter the island like strange ghosts. In addition to lounging in the sunshine, Will worked on extracting the old, leaking hot water heater only to discover he needed some different tools, so we made do without. As more and more boats arrived to take advantage of the fine summer-like weather, we decided to move on.

Having sailed by it many times, we decided to pick up a mooring at neighboring Chebeague Island, one of the largest year-round inhabited islands in Casco Bay. I reached out to Eliza who has a house there and whom I’ve met a couple times through a friend. On our walk around the island, we met several people who knew her and finally made contact. She directed us to her house through the woods and met us on the path, which took us by two yurts that she rents of AirBnB, one of which is an authentic Mongolian yurt ( The island is also home to the famed Chebeague Island Inn and restaurant, where we had a wonderful meal on the last weekend of their season. What a treat! Rowing back under the stars in the cool October night felt magical and firing up the propane heater was pretty special too.

The next day we spent cleaning the boat of the mold that accumulates with so much moisture. As the wind picked up, we decided it was time to head back and finally take care of the hot water tank. The sail in 20 knots of wind was one of the most exhilarating we’ve had, where we hit 9.5 knots as we surfed down a wave into Whitehead Passage past Cushing and Peaks. It was quite a spectacular last sail of the season!

We picked up a mooring at Peaks and had a nice walk ashore, complete with a delicious brick-oven pizza from a mobile food-truck. Being so close to Portland, Peaks has such a different vibe from the other islands we’ve visited—nowhere near as remote and way more “hip.” That evening, there was even a wedding on the island where the music punctuated the evening with the sharp notes of oldies music wafting out over the water. On our walk, we saw the bridal party on the beach for a photo shoot.

Rather than spending another week on our rolly mooring, we decided to check out Spring Point Marina in South Portland. The marina is just next to our mooring and is one of the newest and largest marinas in Maine, chock-a-block with mostly motorboats. As luck would continue to have it for us, the dockmaster is a former classmate of my kids, and he was more than happy to extend us the end-of-season rate, which was a great way to ease our way back ashore. Given the good night sleeps combined with the reasonable rates, we decided on the spot to sell the mooring and use Spring Point as our base in the shoulder seasons before and after DiMillo’s.

First order of business was to replace the hot water tank, which thankfully went reasonably smoothly. Since we are now plugged into shore power, the reward is hot water coming out of both faucets all the time—a significant upgrade from the summer when we only had hot water after running the engine. Over the next week, we spent much of the time ashore—hiking in Bath with a friend who was an exchange student in Sweden with me in 1976 and whom I haven’t seen in 40 years; helping my cousin clean out her father’s 1800s farmhouse; and visiting with family and friends, which is after all why we are here in Portland as opposed to say, the Bahamas, which might yet be in our future. The pull of a land base in the off seasons that feels more like a boat is still there as we continue to look at real estate, but it waxes and wanes like the moon.

And today, five days into our stay at DiMillo’s, we’re settling into our new home, which includes hot showers ashore, walks to the fish market and along the Eastern Prom, running heaters to stay warm, and getting to know the almost fifty other hearty souls who are choosing to live on their boats as the temperatures drop. Our neighbor has already helped us fix a leak we’ve had for some time so now our bilge is dry for the first time all summer!

With this transition now complete, we realize it’s time for Season 2 of Nirvana, namely winter, which will include three months in Sicily aboard Cascade II, my father’s former Jeanneau 41. To be continued . . .

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