
Time was that mapmakers would append the designation “Here be dragons” to those portions of the globe still unknown to them. But the terrors of the unknown pale in comparison to the fog, tides and rock (and lobster pot!) strewn harbors of coastal Maine—or so I thought until I actually went there to see for myself.
In fact, while there are certainly plenty of ways to get in trouble there—same as any charter ground you might explore—Maine is no more dangerous than any other place else you might want to try chartering. Indeed, it might even be less so, thanks to the extraordinary number of spots to run and hide—or just spend a few extra hours relaxing on the hook—in the event Mother Nature ever decides to throw you a curve.
Charter out of, say, Penobscot Bay and you have immediate access to one of the saltiest and most magnificent cruising areas in the world, replete with sturdy lighthouses perched on various rugged, piney outcroppings of land; wonderful historic harbor towns like Camden or Brooklin; and again, countless nooks and crannies harboring everything from lobster pounds to desolate rocky beaches. No matter what the wind direction, protected waters are only a hop, skip and jump away.

Sailing out of Southwest Harbor in the shadow of Acadia National Park’s Mount Desert, we started out our own charter by spending a night deep in Somes Sound, after which we sailed to the remote island community of Frenchboro for a taste of what all of Maine used to be like in the old days—truly magical, and more than worth dodging a few (hundred) lobster pots along the way.
Not only that, but bareboat charter in Maine and you aren’t going get just another boat. In keeping with the region’s storied shipbuilding tradition, the charter fleet here is stocked with yachts boasting those same heartbreakingly beautiful lines that caused many a sailor to fall in love with the sea in the first place. Think Tartan, Sabre, Nautor’s Swan and even the odd custom ketch or schooner.
Morris Yachts and its parent company, Hinckley, also offer a small fleet of their two storied boat lines for charter—which is just as well given that even the most humble boat in this part of the world tends to be a real looker, not to mention the fact you’ll have Maine’s famed windjammer schooner fleet for company. South Florida or the BVI this ain’t!
AT A GLANCE
Getting there: For much of the East Coast, the best thing to do is just drive. New York City to Rockland is roughly six hours. Otherwise, Bangor International Airport is a little over an hour from the heart of cruising country, while the smaller Bar Harbor Airport lands you even closer to the action.
When to go: The season opens in June, but July and August are typically less foggy as things have had a chance to warm up a bit. If you can get away for shoulder season in the early fall you’ll have the place to yourself with all the peace and quiet you could ever want, although some smaller businesses may be closed.
Where to go: Bar Harbor, Southwest Harbor, Camden, the Cranberry Isles: Mid-coast and Down East Maine offer everything from quaint towns to empty rocky shores providing something for everyone.
Charter Options
Bucks Harbor bucksharbor.com/charters
Johanson Boatworks jboatworks.com/maine-charter-fleet.php
NorthPoint Yacht northpointyachtcharters.com
Morris Yachts morrisyachts.com/charter/charter-fleet/
March 2017