Falling in Love with Maine

Written and photographed by Craig Kaminer

Since 2016, I have been lucky enough to sail over 8,000 miles in and around New England, down the entire East Coast, through the Bahamas, around Key West to Tampa Bay, and back again. My wife Debbie and I, and on occasion, our sons and friends, traveled offshore and via the Intracoastal Waterway, frequently stopping to look around and walk our now 10-year-old chocolate lab, Charlie. But some days, we sailed around the clock to get to an important port before the weather changed, where we would wait until Mother Nature returned to a more moderate and predictable pattern. While each port we've visited has been unique in its own way, perhaps our recent trip to Maine this past summer was the most memorable. I had seen pictures of the great towns, the lobstermen, rocky coastlines, and fog in every imaginable book and website I consulted. Still, nothing prepared me for the Maine experience, even my enthusiastic friends and colleagues who have summered here for years.

Sailing from Newport, Rhode Island to Sorrento, Maine, (across the bay from Bar Harbor) required a flexible itinerary, patience, and a minimum of two weeks. And, even then, it would have been better to explore this under-appreciated jewel for a month or more. So, amid the pandemic, which afforded us the flexibility to be away from St. Louis for almost four weeks, we set out to discover what the fuss was all about Down East.

After a few quick stopovers at ports in Massachusetts and New Hampshire, we sailed to Portland, Maine. While it's worthy of an even longer stay, we stopped for two nights at Fore Points Marina (forepointsmarina.com) as we awaited friends from New York to join us. Portland is vibrant with excellent craft breweries, seafood joints, galleries, great shopping, and museums that appeal to its hip community of residents and visitors. Mega-yachts, including the 312-foot Kismet at the end of our pier, share dock space with transient yachtsmen and smaller craft.

We had the best lobster rolls ever (at Highroller;highrollerlobster.com/), amazingly fresh oysters farmed the same day from nearby coves, and a great dinner at Scales (scalesrestaurant.com). At the crack of dawn, we woke to walk Charlie and hit the fog-filled open water to Rockland.

The coastline was exquisite, but it was only visible for half of the day. The balance of the sail, we were socked in with fog, fog horns, and surprising blips on the radar that, out of nowhere, heralded vessels on a collision course. A severe weather forecast ended the day early. Fortunately, the storm passed quickly, and the sun came out by dinner, so we ventured back into town on our dinghy for a special meal at Hill's SeafoodCompany (hillsseafoodco.com).Rockland turned out to be a great stopover, albeit not as hip as Portland or as quaint as some of the places we stopped in the days to come. Still, we found some outstanding restaurants, a handful of worthy galleries, a boardwalk for a late-night stroll, and some of the cheapest diesel fuel on earth (under $2 per gallon).

As we pulled into Boothbay Harbor, a small picturesque town reminiscent of Charlevoix, Michigan, the scenery started to appear what we'd imagined Maine would look like: boulders on the shoreline, tall pine trees, lobster pots socially distanced no more than six feet apart, stunning homesteads passed down from generation to generation and friendly people with thick New England accents. We had a relaxing lunchoverlooking the harbor (Fisherman's Wharf Inn; fishermanswharfinn.com), shopped the town, hiked to the other shore, and picked up eight freshly steamed lobsters for $40.

From Boothbay, we sailed to our target destination of Sorrento just across the bay from Bar Harbor. We added Sorrento to our itinerary at the behest of our friend Steve Dwyre and his sailing companion Cindy Cady. They live there in a 100-year-old waterfront home overseeing his 46-foot Oyster sloop named Willow. For years, Steve has urged us to visit, and we were pleased that the town was more beautiful than he said it would be. We found the town's only rental mooring, and for $25 a night, we moored in a well-protected harbor just a short dinghy ride to the town dock. We quickly discovered that Mainers prefer row bows to inflatable dinghies, and most docks are crammed with them. It makes for a nice picture, and while it seems impractical to us, we rowed when we could to feel local and get some exercise. Steve and Cindy have been cruising continuously since 2016, filling their passport with stops in numerous ports of call. Karl Gerchow and Conner Esworthy, a young couple they met in Honduras this past winter when the pandemic forced them to stay put, were also staying with them. Karl and Conner met while working in finance at JPMorgan in New York City, and soon realized they shared a dream of buying a sailboat and enjoying a liveaboard lifestyle. I'm sure their friends and family all thought they were crazy (especially with their Ivy Leagueeducations on sabbatical), but they have been sailing for three-and-a-half years and seem happier than most.

For four days, Steve's house became a sort of sailor's halfway house. We told stories, sat by a fire (yes, it was that cold at night), learned tocrochet, painted rocks, watched movies, cooked dinner, drank wine, and discussed our upcoming sailing plans. Since then, we have stayed in touch with Karl and Conner, adding them to our growing list of sailor friends who understand us better than some of our land-bound acquaintances do. On one of our days in Sorrento, we visited Bar Harbor and Acadia National Park. Bar Harbor was great, but a little too commercial and not exactly what we were looking for. Acadia was beautiful and the perfect place to hike, take photos and clear our heads with brisk fresh air. We hiked around Jordan's Pond, which I was promised would be an easy two-to-three mile jaunt that ended up being closer to six. My hips were stiff, my muscles a little sore, but I am delighted to have done it. I am sure I would say the same thing if I did an Ironman.Another day we hunted sea glass and heart-shaped rocks on a rock bar connecting two small islands. It's the perfect spot to hang out until high tide gradually separates the pair of islands. Soaring bald eagles, ospreys, and harbor seals made the afternoon magical, even though I thought Steve said we were boating to a bar for drinks. There was bar (a rock bar), and we did have drinks, but it proved I need to be a more careful listener. That night, Debbie and I cooked a "thank you" dinner consisting of lobsters, fresh corn, asparagus, and a locally baked blueberry pie. We pulled out of Sorrento Harbor on Saturday morning, planning to reach Camden by evening. The winds grew throughout the day with 35-knot gusts blowing straight at our bow. Rather than fight the aggressive conditions, we altered our course and pulled into North Haven. Much to our surprise, we found one of the best-curated shops we have seen in some time (The North Haven Gift Shop, located Main Street; northhavengiftshop.com) and walked a couple of miles before returning to Va Bene. Due to the howling winds, we decided to fix dinner on board, stream the latest Yellowstone episode, write in our journals, and get a good night's rest.

Our next stop was a little town called Five Islands, so named because it is literally surrounded by five small islands on Sheepscot Bay's edge. It was as pretty as a postcard, with the main attraction being a lobster shack (Five Islands Lobster Co.; fiveislandslobster.com), which boasts some of the state's best cold-water lobsters. When you are called to the counter by one of the family members (in this case, it was a boy around 12 years old), you told him how big of a lobster you wanted, and he fetched one that had been caught earlier in the day, weighed it and charged accordingly. A duo of two-plus-pound lobster dinners rang up less than $50. The people we met at the socially distanced family-style tables were just as incredible.We continued to Isles of Shoals, an off-the-coast of Portsmouth grouping of three islands jointly owned by New Hampshire and Maine. In good years it is home to seasonal residents, students, and volunteers who reside there studying art, history, sustainability, spirituality, and yoga. We did check out Star Island, which looked the most inhabited, but found a "closed for the season, no trespassing" sign. Charlie had to go, so we trespassed for a few minutes, saw the ancient grave sites of 10 or so people who chose to be buried there over the few hundred years it was semi-occupied, and headed back to the boat for cocktails and dinner.

From Isles of Shoals, we sailed most of the day in the rain to Provincetown (aka PTown) again, where we finally got a reservation in one of thetop-rated restaurants (The Mews; mewptown.com) according to TripAdvisor. We'd been on the lookout for whales all day and finally witnessed two massive Humpback whales breach and put on a show for tourists gawking on the nearby whale watching tours.Uponarrival in PTown, we suited up to take Charlie for a walk and check out a few of the stores we had missed on our earlier visit. With the foul weather, an irritable outboard engine, and two forgotten face masks, we returned to Va Bene, doffed our raingear,took much needed hot showers, and made our own five-star meal. The sun was out the next morning, so we spent some time in Provincetown before heading around the outside of Cape Cod to Nantucket.It was another long, wet day of sailing, but by the time wearrived near sunset in Nantucket, the skies had cleared, and the charm of Nantucket welcomed us. We were retrieved at the town dock by friends who had rented a house there through September. We enjoyed cocktails, a hot shower, and putting on "real" clothes for a fabulous meal at Queequeg's (queequegsnantucket.com).

An additional day of life on land allowed us to enjoy the beaches, lunch in town, a couple of great book shops, and a harbor full of mega yachts and best-in-class sailboats which can entertainan old salty dog like me for a week or more. There aren't many places like Nantucket, which combine a whaling town's authenticity, a retreat for the well-heeled and well-traveled, and the yachtsman. Unfortunately, the diesel was $5 per gallon here. Perfection has its price. On Saturday, we woke up early to a strong, steady wind which sailed us at least 7.5 knots to our home port of Portsmouth, Rhode Island (just four miles inland of Newport, Rhode Island) in record time and not having to use any of the expensive diesel I filled up on just in case. We tied Va Bene up for the first time in two-plus weeks, hosed her off, and for the next couple of days, restored her to her pristine condition before driving home to St. Louis so I could get back to work and write this story.Rocky coastlines, lobster pots and boats, fog, rain, and windy conditions make Maine a challenging place to sail. Still, it is one of the most magical places we have ever been to. I am not sure when we will return, but Maine will always be close to the top of the list from now on, and if you ever want to come aboard, please let me know.