Maine: Rockland, Southwest Harbor, Rockport
Rhode Island: Newport
Connecticut: Mystic, Norwalk
Vermont: Burlington (Lake Champlain)
New York: Henderson Harbor (Lake Erie, Thousand Islands)
Being There: Midcoast Maine
There’s a reason why Andrew Wyeth, Winslow Homer, Edward Hopper, and other American masters chose to paint coastal Maine scenes and why the Rockefellers (and Martha Stewart) built lavish summer homes there: its history, rocky islands, peaceful villages, hard-working fishermen, and simple beauty—even the fog—feed the soul. All these things make the Maine coast arguably the best cruising ground in the continental United States.
In the south, Casco Bay offers picture-postcard anchorages on its rocky islands, some uninhabited, others with tiny year-round communities of fishermen, many of whose families have lived there for generations. These special places are only a relatively short sail from the hip city of Portland and the outlet-shopping mecca of Freeport.
Farther up (or down, as in Down East), the coast reveals oodles of snug little harbors that provide excellent protection and variations on a basic theme—stunning natural beauty and charming coastal life. It’s easy to spend weeks exploring without ever stopping at the same place twice. And that’s before you reach the jewel of Penobscot Bay—a must-not-miss destination on any cruising itinerary. Here you sail in company with traditional windjammers and dodge the ubiquitous lobster pots before taking time ashore to hike the hills around Camden or shop along Rockland’s Main Street. Only a short sail across the bay, the vibrant communities on the islands of Ilesboro, Vinalhaven, and North Haven are quintessential coastal Maine. Stop in Pulpit Harbor to watch the sun set or anchor in the shelter of the Barred Islands to experience the peace of having a fogbound anchorage all to yourself.
If you time it right, you can experience the magic of power-reaching on prevailing summer southwesterlies through narrow, twisty Fox Island Thorofare. The cruising grounds become more rugged, remote, and (dare I say) more beautiful, the farther east you venture. Here, the relaxed sophistication of Northeast Harbor, the stunning beauty of Soames Sound, and the power of Cadillac Mountain and Acadia National Park are all within reach. Tiny villages in the area have some of the freshest lobster you’ll ever eat and some of the loudest unmuffled lobster boats you’ll ever encounter. But that’s all part of the charm. Bill Springer
Northern New England: Our chartering season runs from early June to late September, and our peak chartering time is late July and early August. The best time to sail in Maine, I think, is late August and early September, when the days are usually clearer, the anchorages are less crowded, and you’re most likely to have a good breeze all day. The typical summer wind is a southwesterly sea breeze at 10 to 15 knots, and summer sailors need to be prepared to deal with fog on any given day. Mary Johanson, Johanson Boatworks, Rockland, Maine
Southern New England: We’re open for chartering from the last week of May through Columbus Day. My favorite time to sail here is, hands down, September, when the water is warmest, there are fewer tourists, and the cooler nights make for great sleeping. The winds usually stay out of the southwest until the end of September, rising to 15 to 18 knots in the afternoon—perfect conditions for heading to Martha’s Vineyard and Nantucket. Even in Newport it can be hot and humid in August. Brian Blank, Bareboat Sailing Charters, Newport, Rhode Island