Chartering Mount Desert Island

From my vantage point aboard a Cal 31 sloop sailing out of Southwest Harbor, the cottages look more like castles, with immaculate grounds atop pink granite cliffs that drop into the chilly Maine waters below. The day couldn’t be more perfect for sailing
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John D. Rockefeller. Edsel Ford. Joseph Pulitzer. J.P. Morgan. Martha Stewart.

Capt. Robert lists off these conspicuous names as we whiz by their even more conspicuous “summer cottages” dotting the shoreline of Mount Desert Island, Maine. From my vantage point aboard a Cal 31 sloop sailing out of Southwest Harbor, the cottages look more like castles, with immaculate grounds atop pink granite cliffs that drop into the chilly Maine waters below. The day couldn’t be more perfect for sailing: it’s blowing 10 to 15 knots with temperatures in the high 70s and not a cloud in the sky. I’m beginning to understand why Martha likes it here. 

As we gaze beyond the cottages, Capt. Robert begins another list: Cadillac, Champlain, Acadia and Penobscot. This time he’s naming the round granite peaks that form the skyline of Acadia National Park—the tallest mountains on the Atlantic coast north of Rio de Janeiro. Mount Desert Island, or MDI, is home to 10,000 permanent residents, but Acadia National Park, which covers nearly 50 percent of the island, receives over 2.5 million visitors a year. 

MDI is shaped like a lobster claw (an apt comparison, given the massive number of lobsters caught in the area) with its two “pinchers,” or peninsulas, separated by Somes Sound. Somes Sound, in turn, empties into Great Harbor, which during the summer is regularly bustling with gorgeous racing and cruising sailboats including Friendship sloops, International One Designs and several locally built Hinckley and Morris designs. 

We’re on a day charter with Mansell Boat Rentals, located near Southwest Harbor, which offers both day and week charters. Capt. Robert, our guide for the day, is about as salty as they come, complete with a husky beard, a sailor’s tan and enough stories to confirm he’s lived a rich life at sea. 

If you’ve got only a weekend to spend on MDI, follow Capt. Robert’s day-charter itinerary, which starts out by going directly up into Somes Sound. Named for Abraham Somes, the first permanent resident of the island, Somes Sound is the only fjord on the Eastern Seaboard, and is bordered by Acadia Mountain to the west and Norumbega Mountain to the east, with 125 to 175ft depths throughout. At the mouth of the five-mile fjord—“the Narrows”—you’ll see grassy Fernald Point, where a group of French Jesuits settled in 1613. By contrast, across the Sound you may also see the 139ft megayacht, Rebecca, resting at her mooring and offering an interesting intersection of old and new that defines much of this cruising ground. 

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After leaving the Sound, dip into Valley Cove for a break from the wind, and then bear away and head east. As you sail past Northeast Harbor, allow some time to ogle the beautiful boats on their moorings before continuing on to Bear Island, where a lighthouse flashes every five seconds, guiding those same beautiful sailboats home. 

Once you pass Seal Harbor—home to the Ford family compound—you’re headed for blue water. Before you get there, though, beware the rocks of East Bunker Ledge marked by a faded white-stone pyramid. Placed there as a tribute to the many mariners who have died at sea, the pyramid now stands as one of the country’s oldest navigational beacons. The Ledge is also home to many animals, including great seals, harbor seals, ospreys and cormorants. 

As you follow the cliff-strewn coast to the north and east, you’ll see Otter Point and then Thunder Hole, both popular attractions for park visitors. MDI was formed by molten magma that bubbled into a string of mountains and spent a millennia getting carved and shaped by retreating glaciers. Today, the result is a dramatic coastline of pink granite that shimmers in the sunlight when viewed from the water. 

After absorbing this scenery, head back toward Great Harbor, stopping at Little Cranberry for a visit to the Islesford Dock Restaurant or Maritime Museum.

On your way to Southwest Harbor, cruise up to Sutton Island and look for the 100-year-old osprey nest perched on an outcropping of rocks. Tie up back at Mansell Yachts and cap off the day boiling your own lobster at the nearby Seawall campground. 

Southwest Harbor offers an ideal itinerary for the weekend warrior, but if you’ve got more time, there are literally hundreds of islands within cruising distance. You can also explore more of Acadia via hiking trails on Isle de Haut, the Schoodic peninsula and Somes Sound, or sail farther afield to Merchant’s Row, the fabled Eggemoggin Reach, the islands of North Haven and Vinalhaven, and the towns of Camden and Rockland. 

Whether you’re looking for a day filled with history, a weekend filled with adventure or a week filled with scenery, you’ll be able to find an itinerary on MDI to suit your fancy. After all, it’s good enough for Martha.

Photos by Meredith Laitos

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