A Down East Summer Cruise: Part 2

Serendipity rules on a sailing vacation full of remarkable encounters and reunions.


Boothbay Harbor, Maine. Elaine Lembo

I’m walking down the road leading to Cundy’s Harbor village in Maine when I hear a vehicle stop alongside of me, and the window roll down.
“Land’s End?” asks the driver.

“Yes!, Yes!, that’s us!” I reply, stunned. We live in a time of social media, but this fellow didn’t strike me as the type who’s plugged in 24/7. He must have seen us when we’d anchored the night before at nearby Ridley Cove, to the west of a shipwreck, in a persistent rain that left us soaked to the bone.

Our 20-mile long motorsail from Portland marked the official kick-off to the second half of our Down East Cruise, and we planned to celebrate this momentous achievement of crew and 1935 Crocker ketch with a convoy of sorts. Former CW colleague, now Sail editor, Charlie Doane, had just seen his family off to Ireland at Logan airport in Boston, and he was spending the week as a singlehander again aboard_ Lunacy_, his hard chined aluminum cutter. Ridley Cove was our appointed meeting place, and as soon as we’d settled in, out rolled the celebration feast of pasta and salad, the boxed red wine, and the Cuban cigars (which the captain had squirreled away just for such an evening.)


Charlie and his sleek singlehanding machine were in forward motion mood, but Capt. Rick Martell, my other half, and I decided to hang back, and savor the tree-lined, pristine, quiet spot for another day. “Well then, you have to got into town tomorrow if you stay!” Charlie advised.

And that’s how Dave Woodman, the driver who stopped dead in his tracks on the village road, found me. “I knew it had to be her,” he said of the boat. ” I know that hull, those lines. It’s Land’s End, all right. I buzzed around her several times in the cove.”

Turns out, at one point Dave worked for Crocker’s Boat Yard in Manchester, Massachusetts. “I knew Skip when he was just a little kid with a runny nose,” reminisced Dave of young Skip, who’s now running the show there. Dave himself is also now building a sailboat at home in his garage when he’s not busy with the village fire department and running a landscaping business. “We used to live aboard our boat in Manchester in summer, and the owners practically had Land’s End moored in the middle of the channel.”


On that matter I could easily agree; we did the 2012 annual Crocker Memorial Race in July, and locals pointed out exactly where Land’s End floated on her mooring. In Manchester’s narrow harbor, I could imagine how the boat stood out among others.

I bid Dave farewell and continued on my stroll into town. There I visited Watson’s General Store, reputed to be Maine’s oldest general store, and a little farther away, I took in the Holbrook Working Waterfront, a mini village unto itself with a snack bar, gift shops, gallery, and another general store. The shops are the focus of the Holbrook Community Foundation, formed in 2006 as a nonprofit to preserve the waterfront as it is and prevent private development. For more details contact the foundation (

Now I must bid farewell. In a few minutes, Virginia Wagner, formerly the captain of the crewed catamaran Matau (upon which I sailed and wrote a story for CW some years back) is coming to fetch me and lend us a car so we can reprovision. Tonight we’ll visit Virginia and Jamie Stark, her partner, in their summer setting in Boothbay, Maine, and celebrate with the Maine staple: lobster. Can’t wait!


View photos of the trip in this gallery.
Read Part 1 of ‘A Down East Summer Cruise’ here.


Email Newsletters and Special Offers

Sign up for Cruising World emails to receive features on travel destinations, event listings and product reviews as well as special offers on behalf of Cruising World’s partners.

By signing up you agree to receive communications from Cruising World and select partners in accordance with our Privacy Policy. You may opt out of email messages/withdraw consent at any time.