
During our three long weeks on the hard during a heat wave in the Chesapeake, I dreamed about our reward: cruising Maine for the rest of the summer. I’d never been to Maine, but all the little islands and seaside towns to explore, along with the promise of lobster rolls, created enticing-looking cruising grounds. The cooler temperatures would also be a bonus. After a wonderful, restorative week-long stop in Stonington, CT for the 4th of July, which we spent with cruising friends and their family (thanks Susan and Brian!), we had a beautiful weather window to sail 200 miles to Portland.
At dawn, we were welcomed by lobster pot buoys, which only increased in number as we turned from the Atlantic into the peaceful confines of Casco Bay. But the beauty was just as I had imagined: rocky shores, pine trees and little homes perched on the edges of islands. The smell was also incredible. As we anchored in the lee of our first overnight spot, we were like dogs with our noses out the window, sniffing the heavily pine tree-scented air. It reminded me of being a child in the mountains of Colorado and the first whiff of fresh air when I’d step out of the car after driving up from Denver for a weekend.


We spent a pretty idyllic three weeks in Casco Bay, hosting family and friends who traveled in and out of Portland. Picking them up and dropping them off in South Freeport was easy and there were a variety of great anchorages located just an hour or two away in the bay. We hiked, built bonfires on the beach, and explored small rocky islands. We even hit up Freeport’s famous LL Bean campus. It was everything we imagined Maine would be, albeit a little colder and foggier than we were expecting for July. The Harraseeket Lunch & Lobster shack located right on the pier at South Freeport was a bonus. It has been there for at least 60 years, according to the dockmaster who worked there as a teen, and is owned by the same family. It’s a BYOB joint, with picnic tables and windows to order and pickup. In our three weeks in and out of the area, the place was packed all the time, by tourists and locals alike—we ate there four times and were tempted to go back pretty much every night we were in the harbor.

As soon as our last round of visitors left, we headed further east to Penobscot Bay where we’ll spend most of the month of August. The area, which includes Camden, Rockland, Belfast, Vinalhaven, Deer Isle, and is a close hop to Mount Desert Island and Acadia National Park, is so far just as pretty as Casco Bay—maybe prettier, with less people so far. The anchorages and towns feel that much more rural and the cruisers seem to be full-time, rather than the weekend boaters closer to Portland. As we enter into August, the days seem to be sunnier and warmer, with less fog. But the mornings remain pleasantly brisk when we’re on deck with a morning tea. I, for one, am happy to have a cooler summer and pull out all the sweatshirts and pants we’ve had packed away for the majority of our trip.

The two constants remain the lobster pot buoys and the beauty of Maine. We keep our transits relatively short, both for the amount of concentration it demands to avoid snagging a pot and because we don’t want to miss the beautiful anchorages in between. The buoys marking the pots are no joke; everywhere—EVERYWHERE—is strewn with them. It’s often hard to pick our way through, as we slow down to weave in between, trying to find some kind of path. It’s honestly amazing that any lobster could scuttle across the ocean floor and avoid getting itself trapped in a pot. Even so, we could easily spend several years exploring the ins and outs of the peninsulas and islands. It beautiful, interesting cruising and we simply don’t have enough time here to see it all.
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