We are off! The Bensley Great Loop 2019 begins!

Sorry for the delay in writing an update – finding Wifi has been more difficult that I anticipated!

We departed from the Back Channel in Kittery on Tuesday – June 4, 2019 as hoped. First crew on our GL journey was captain Dean, Karen, and good friend, Geordie Hall. It felt amazing to be finally off and heading south after months of planning, years of discussing – we are doing it! Beautiful sunny light wind day to get our sea legs adjusted.

From Kittery, we sailed south to Gloucester MA, going first through the picturesque Annisquam River, a tidal, salt-water estuary  connecting Annisquam Harbor on the north to Gloucester Harbor on the south. It was so pleasant to ride through the ~ 5mile river on a quiet day, with less busy boat traffic than other times we’ve cruised through in the past.

The “unusual” photo was taken was going thru the Annisquam river railroad bridge, a “selfie,” in a mirror mounted on the bridge so boats could see oncoming traffic through the narrow passage.

We were able to pick up a mooring in Gloucester Harbor, an old fishing and canning harbor that was busy with rowers and fisherman, plus a few of us recreational boaters.

This “Manufactory” began in 1863, manufacturing America’s first copper paint, playing a vital role in international maritime history as well as in the development of Gloucester as a major fishing port. Thanks, Al Reetz, for sharing that info!

From Gloucester, we continued south. We had a lumpy and rocky cruise that day, perfect for a real “shake down” cruise for trawler Clare. Overall, the boat did well (as did captain and crew) in the rough-for-a-trawler seas and we eventually ducked into Scituate Harbor as the weather was predicting severe thunderstorms. As always, Dean keeps a keen eye on the weather reports and plans our routes cautiously – thankfully!

My mom’s family, the Piccolos, had a summer estate (?) in Scituate, and I remembered many family trips to Scituate. My mom used to tell how she earned money as a teenager by “mossing,” which was gathering seaweed to be used as a thickener for medicines such as cough syrup. I still have relatives in the area, including my brother George, and several cousins. We were able to connect with my cousin Christopher O’Halloran and his lovely wife, Susan, and had a fun evening catching up with them.

Captain Dean had us up early and back out to sea to catch the helpful current and to avoid the sea building up with waves. Thankfully, the thunderstorms all seemed to have missed us during the night and the weather was fair again.

Our journey on June 6th brought us through the Cape Cod Canal, a man-made passage connecting Cape Cod Bay in the north to Buzzards Bay in the south, and is approximately 7-10 miles long. Last time we had been through had been on Genesis, our first sailboat, when the kids were young (12?). I also remember sailing through with Dean and Clare, Dean’s parents, on their beautiful sailboat, Transit, probably in the 19080s. Again, Dean timed the current to our advantage and we cruised through at a good-for-a-trawler pace, passing under the Sagamore and Bourne bridges. We had company with freighters and tankers also traversing through. Puts our 36′ boat into perspective.

Buzzard’s Bay! Dean and his family sailed in this area when he was growing up, and his dad, Dean E, reminisced that his favorite adventures in this area were sailing to Martha’s Vineyard for our (still) annual Memorial Day weekend with family and friends, hosted by the Elkinds. I think there are many more stories to be told.

We anchored in a very quiet and peaceful Pocassett Harbor, off of Bassett Island. Although beautiful, the island is private and marked “no trespassing” so we were unable to explore except by dinghy. Yet another peaceful and quiet night! We are adjusting to boat life and boat time and even boat sleep! Oh, and boat cooking!

Friday, June 7th, we continued through Buzzard’s Bay, heading for Cuttyhunk Island, the outermost of the Elizabeth Islands in Massachusetts. Beautiful, peaceful, and we were well ahead of the summer crowds. Moored in the inner harbor, and walked a good portion of the island – the hill overlooking Martha’s Vineyard, and along the beach out to the point. The rosa rugosa (“Beach plum”) was prolific and smelled so lovely. I wanted to capture that smell! The rosa rugosa was intermingled with beach pea for a stunning display.

Small island life is fascinating to us “main-landers.” The island has a small scale version of the necessities – post office, school, market, library – that are each open for a few hours each day. The harbormaster is also the police, animal control, fireman, and probably more – he was fascinating to talk with. Apparently only 20 people winter over on the island, and the main income seems to be from mooring and dock rentals, the raw bar boat that services the boats, and the fish and lobster available on the wharf.

Another wonderful day, capped off by a stunning sunset over the island.

Good bye quiet island life, hello busy seaside sailing center! We next visited Newport RI, which was busy with boats of all sizes (so many mega-yachts!), people from various countries, and appeared to be gearing up for races next week. Here we met up with Judy Bowen, friend and partner to Geordie, who delivered a needed part to fix the thruster and to pick up Geordie at the end of his cruise. We walked to the Cliff Walk along the ocean side and peeked at the grand mansions including The Breakers and Salve Regina College. Hustled and bustled to get showers, ice, and restock the fresh foods, and said thank you and good bye to our first GL guest, Geordie. Have a great safari in Africa, Geordie (and Judy) and thank you for all the good conversations (and chocolate and Grouse!)

On Sunday, June 9th, we woke early to a calm harbor and more sunny skies – we have been so blessed with better-than-anticipated weather! Cruised 5 hours south on fairly calm seas, past lots of fishing boats but, again, few recreational boaters as yet. And, disappointingly, no whale sightings. My work partner PT, Kirsten Berthiaume, secured us a mooring in Stonington CT (across from Fisher’s Island NY) at the start of Long Island Sound. Her family has boated here for years and welcomed us to their mooring and their yacht club (Wadawanuck) for the night. Lovely family oriented club with a beach, swim area, sailing program, and extensive dockage (with a waiting list, of course!). Thank you, Kirsten, parents Ed and Elaine, and brother Craig for hosting us for a night.

We are getting closer to New York City and soon will be inland on more protected waters -quite the change for us! Thanks for reading this far and hopefully I’ll find Wifi a little more frequently to post more regularly.

Categories: June 2019


  1. Thanks for the exciting and detailed update!


    • Thank you so much for giving us land-lovers such an interesting report of where you are and what’s happening. I of course especially loved hearing about the New England portion of the trip. Fascinating—but I’m not sure I would like being on the water. Thanks again!


  2. What a wonderful start! Enjoy enjoy everything! Sending love…


  3. Thanks for catching us up to speed with your detailed, fun stories and fabulous pictures! Glad the weather and seas are cooperating! Love to you both.


  4. Really love reading of your adventures! My first husband and I had a 27 foot sailboat that we sailed as far as yarmouth Maine and all around the cape and islands. It was quite an adventure. I’m really enjoying reading of yours. Enjoy New York, it will be fun by boat!, stay safe and enjoy!!


  5. Thanks for the update Dean and Karen! Sounds like things are going great so far.

    Liked by 1 person

  6. Beautiful photos! – thanks for the updates


  7. Beautiful photos! thanks for the updates and travel log. Love seeing your adventures.


  8. Love!!!


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