Sailing Among the Islands in Maine

And so it was. The small, crowded harbor glittered in the evening sun as we traded tacks through the narrow entrance channel with a gray-haired lady solo-sailing a pocket cruiser and grinning like she’d just hit the jackpot. Coveside Marina had open moorings for $40 a night, and we grabbed one.
Coveside Marina dominates Christmas Cove, offering a bar, a good restaurant, and showers for guests. We got a table quickly; the steamed mussels were superb, the service fine, and everyone was friendly, if frazzled. But after the easy rhythms of Burnt Coat, it felt a bit forced. Vesey ran afoul of a little catfight between our waitress and the hostess, and when we repaired to the bar for a nightcap, you couldn’t hear yourself think for the racket as a pair of guitarists/singers vied with the Yankees and Red Sox on a big-screen television for the crowd’s attention. It had that schizo mainland feel to it, and never a friendly wave from anyone. When we checked the chart book back at the boat, Rutherford Island indeed had that telltale bridge connection.

Next morning, we plotted a course down to Casco Bay, a place with which I was keenly familiar, having spent many summer vacations on Chebeague Island when the kids were little. Chebeague is a classic unconnected outpost, green and uncrowded even though it’s just a short ferry hop from Cousins Island and only 10 miles from the booming metropolis of Portland, Maine’s biggest city. Chebeague is the largest island in Casco Bay yet sports no liquor store, no movie house, no cabaret. Gazing out from the cliffs on the southwest end, it’s all wildness and wet—from the Outer Green Isles to Jewell Island and Halfway Rock, with many a nameless, treacherous, mussel-covered rock shoal that disappears at high tide.

We grabbed a mooring under the loom of the ramshackle wooden hotel on the west side and waited for someone to come out and demand money, but no one did. The mooring said “Hotel” on it, so we did our duty and trekked up the hill, ducking errant tee shots from the nine-hole golf course that cuts across the main road, plopped down on the hotel’s wide, shady porch, and ordered ice-cold beers. It’s the only place on the island where you can get a drink and a meal, and the porch is made for sunset, which obliged us perfectly. And nobody ever sought a penny for the mooring.

We lingered long enough at Chebeague to sample Casco Bay’s treats, including a day trip to Eagle Island, where Robert E. Peary, who claimed to be the first man to set foot on the North Pole, had his summer retreat. The Peary place is just as he left it almost a century ago thanks to the oversight of the state, which maintains it as a public park. You can anchor or moor there and explore the house, rub your hand along the narwhal tusk Peary brought back from his Arctic adventures, and admire his musty collection of stuffed birds from around the world. And you can walk the winding woods trails that lead in August to fields of blackberries and raspberries free for the picking.

Casco Bay is largely overlooked by Maine cruisers hurrying to such better-known venues as Penobscot Bay and Mount Desert Island. But it’s worth a stop, with steady breezes and sun-kissed flat water behind the outlying islands and plenty of tricky navigating around the rocks. We had lunch in Potts Harbor, at the tip of Harpswell Neck, where the Dolphin Marina’s restaurant serves the best fish chowder in New England, but we never got time to stick our noses into fjord-like Mackerel Cove, at Bailey Island, or the postcard-perfect anchorage at Jewell Island, where U.S. lookouts once manned concrete towers to scan the sea for invading German U-boats that never came.

You could easily spend a week in Casco Bay, then three or four weeks breezing Down East on the prevailing southwesterlies, and never run short of things to explore. But we had miles to go and promises to keep. Too soon we were off, bound past Cape Elizabeth and over the Bigelow Bight to Massachusetts Bay.

Just for chuckles, we took aim at the far side of common sense, sailing overnight from the sublime to the chaotic. Hey, it was on the way and none of us had been there in years, and who doesn’t secretly crave an evening in a place where the cast of a musical parades down the main street in nothing but skimpy towels while imploring you to spend the evening watching something called Naked Boys Singing?

That’s right, we went from the soft, sweet silence of Chebeague into the circus that’s Provincetown, where we discovered some of the locals there wave at you, too.

Angus Phillips is a CW editor at large.