Summer Sailing: Casco Bay’s Jewell Island

Our much anticipated summer sailing trip has come to a close. My daughter Hannah and I have returned home, exhausted yet exhilarated, with sun-kissed cheeks, giant seashells, and cameras full of images merely touching on the rocky coastal beauty of our Maine to Boston adventure. After an abysmal start to our trip (we arrived at O’Hare only to find that the American Airlines agent had booked us on a flight to Portland, Oregon not Portland, Maine – and yes, I am POSITIVE I specified Maine on the phone), our frustrations melted away the moment we stepped foot on our cousins’ beautiful boat, Calypso (see last year’s sailing trip here). We sailed the following morning to Jewell Island, one of the outermost in Maine’s Casco Bay, anchoring in the harbor known as Cocktail Cove.

Little Jewell Island, just west of Jewell Island.
Little Jewell Island, just west of Jewell Island.

We rowed Calypso’s dinghy ashore that afternoon, and hiked the steep rock wall to trails that led us through the forest, past abandoned World War II Military towers (we climbed to the top of one and peeked through the lookout windows), and down to the Punchbowl, a massive tide pool brimming with marine life.

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Magnificent sculptural roots of a fallen tree.
The magnificent sculptural roots of a fallen tree.

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Hannah, Blake and Sasha hiking on Cove Trail.
Hannah, Blake and Sasha hiking on Cove Trail.
This World War II tower looked like something straight out of The Hunger Games.
This World War II tower looked like a structure straight out of The Hunger Games.
Exiting the woods down to the Punchbowl.
Exiting the woods down to the Punchbowl.

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We emerged from our hike to find we had the harbor almost entirely to ourselves. The evening was spent on board, enjoying some of the best lobster we’ve ever had (my cousin’s wife, Dunja, is an extraordinary cook) and watching the blue moon rise.

Calypso
Calypso

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5 thoughts on “Summer Sailing: Casco Bay’s Jewell Island

  1. Wendy, You take the most breathtaking photographs! And what an awesome adventure for you girls – totally envious! What wonderful memories for you and Hannah! Welcome home, xoxoxo

    1. Thank you so much for your kind words Molly! We will remember the trip forever. And though I miss it already, it feels good to return home to long showers and a big cozy bed (as a sailor yourself, I know you must know how that feels)!!

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