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Sail With Sea Captains in Kennebunkport, Maine

Picture Perfect Kennebunkport on the East Coast of Maine


By Bruce Sach
Created: September 2, 2010 Last Updated: September 7, 2010
Related articles: Life » Travel
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THIS WAY TO COMFORT: The Captain Jefferds Inn provided quick access to the port. (Carole Jobin)

THIS WAY TO COMFORT: The Captain Jefferds Inn provided quick access to the port. (Carole Jobin)


The great thing about Kennebunkport, Maine, is that you identify with the place almost immediately, as everything is in close proximity—not surprising for a town that was established in the 1600s.

Somehow this allows you to focus on your senses.

I notice this immediately listening to doves coo upon our arrival on Pearl Street at our first destination, an old sea captain’s house, the Captain Jefferds Inn.

The Captain Jefferds Inn

Pearl Street unfolded into a deep, rich sunset allowing us to adapt ourselves to the slow pace of this picture perfect little town. The former sea captain’s house is far enough from the sea to never be endangered by it, but close enough so that in the 21st century, it is a mere hop, skip, and a jump to the port.

Built in 1804, the captain’s house is a two-story beauty, built in the Federal period by Captain William Jefferds on the lane leading to Walkers Wharf. His father-in-law was Daniel Walker. Walker is a surname worth remembering when in Kennebunkport! (George Bush, Sr. married a local girl, a Walker, and still lives here on, you guessed it, Walker Point).

The Captain Jefferds Inn house, along with its storied connection to the West Indian trade captain, later belonged to Mrs. Constance Willy, considered the wealthiest woman in Maine in the 1960s. In a town where family background is important, the house has a perfect pedigree.

Sailing, Sailing

The next morning, serenaded by song birds, we caught the Schooner Eleanor for a morning sail. This 40-footer is a labor of love for its captain and owner, Rich Woodman. Descended from boat builders, Captain Rich built the boat from scratch—not surprisingly, he grew up in the house overlooking the wharf.

We walked a brisk two minutes from our inn to the schooner landing on the Kennebunk River. There ended the brisk part of the morning.

We slowly motored down the river to the sea, marveling at the quiet and beauty of the day. To our left, kayakers, small fishing boats, and million dollar yachts rubbed shoulders. To our right, the grounds of the Lithuanian Franciscan monastery provided another oasis of stillness.

TO THE SEA: The Schooner Eleanor was a relaxing way to get to know Kennebunkport, Maine.(Carole Jobin)

TO THE SEA: The Schooner Eleanor was a relaxing way to get to know Kennebunkport, Maine.(Carole Jobin)

The captain’s dog, Hoss, marched about as if counting the passengers, and then, we hit the ocean, heading in the direction of Cape Porpoise.

As soon as we’re on the ocean, we rounded the cape passing St. Anne Church, (where the Bush family worships), and the sails were hoisted.

The rocking motion of the sailing boat took over, a calm sea breeze engulfed us, and the chatter amongst passengers stopped.

The experience was soundless save for a mournful bell attached to a permanent metallic buoy.

Then, action, in the form of George Bush, Sr., lurching out for a morning speed boat ride, catches our attention. His boat takes off in a direction opposite ours, secret service team in tow.






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