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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 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, amazingly fresh oysters farmed the same day from nearby coves, and a great dinner at Scales.

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 Seafood Company. 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 lunch overlooking the harbor at Fisherman's Wharf Inn, 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 live aboard lifestyle. I'm sure their friends and family all thought they were crazy (especially with their Ivy League educations on sabbatical), but they have been sailing for three-and-a-half years and seem happier than most.



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