Island Life, New England Style: Cuttyhunk and Martha’s Vineyard

While it’s not necessarily bikinis and beach towels, the islands in New England offer their own unique charm.  Phillip and I have had an exceptionally difficult time deciding which port(s) in the New England cruising grounds were our favorite. They’re all so lovely.  While Block Island—our first island in NE—struck us, we later thought its “firstness” may have had more of an impact than we realized, when we finally got to experience other islands like cordial little Cuttyhunk and memorable Martha’s Vineyard.  Join us, on our first exploration through these exquisite little NE islands.

July 2022

After our endearing experience watching the nation’s longest-running Fourth of July parade with our entertaining friend Bridgett in Bristol, RI, we sailed across Narragansett Bay to Greenwich Bay and explored Warwick, RI (always makes me think of Dionne Warwick and the Psychic Friends Network … couldn’t help it) as well as Greenwich, RI.  Then it was back down to Newport to stock the boat back up for the next couple of weeks which we planned to spend checking out the first of the Elizabethan Islands, Cuttyhunk, and then the coveted Martha’s Vineyard—a place I honestly thought I would never go in my life!  It always sounded so fancy!  And, to tell you the truth, for half my younger years I literally thought it was just a vineyard owned by Martha Stewart.  Not kidding.  It’s a good thing Phillip plucked this little country girl out of Alabama and opened my eyes to this great big world.  

I don’t think Phillip or me will soon forget our sail from Newport to Cuttyhunk.  The boats that fly in and out of the Newport harbor are simply mesmerizing.  All shapes and sizes and speeds and styles.  The sailing feels like the breath in and out of that historic port.  When Phillip and I left on a brisk day in July (yes, it can be brisk in NE in July) we found ourselves immersed in a fleet of other boats, all with rails buried, tacking and gybing all around us.  It was exhilarating.  And, Ubi was matching them toe to toe.  It is always so rewarding to be reminded that not only did we purchase one of the most comfortable liveaboard monohulls I could imagine, she’s also just really fun to sail!  Outbound did an exceptional job building our (second) baby girl!

The Cuttyhunk Welcome Committee

I don’t think I’ve ever experienced such a cordial welcome to an anchorage.  Cuttyhunk is the first of the Elizabethan Islands in Massachusetts (and so it served as our introduction to Massachusetts) and just a short day-sail from Newport. Phillip and I didn’t know what to expect when we pulled into the protected little cove that serves as their mooring field. We saw a few mooring balls that seemed to be reserved or off limits, and, otherwise, most of them seemed to be already taken.  As we motored around in search of an available ball, a little John boat came out to us, confirmed we were looking for a ball, and took us straight to one that was available—a relief as it’s not ideal to grab a ball and get secure only to be told immediately afterward that you have to get off and move because you snagged an unavailable ball.  But, the assistance of the friendly folks at Cuttyhunk did not end there.  As soon as Phillip and I got Ubiquitous secure on (what we were now sure) was her ball for the next few nights, that same john boat came back out and tied alongside.  

“Ahoy! We’re the Cuttyhunk Welcome Committee!” he said cheerfully.  “Here are some trash bags for when you bring your trash to shore.  They only pick up on Tuesdays.  We’re having a potluck tonight at the dock if you want to bring something and join.  Rum is always popular.  Oh, and breakfast tomorrow morning as well.  Champagne is quite popular. There’s trivia Monday night, too, and Soprano’s is open now.  Great pizza.  Enjoy our little island.  Hope to see you ashore!”  

Everyone on the “welcome boat” waved and wished us a good evening.  It was incredible.  Phillip and I, and UbiQ, felt so welcome!  I think we were invited to every social event they were hosting that weekend.  And we’d just arrived!  Phillip and I looked around at the other boats in the cove and felt like we’d just settled among friends.  We dinghied ashore the following day to explore and were thrilled to soak in another hydrangea-adorned, breathtaking New England island.  Cuttyhunk offered its own charm in that it is so small.  A local at the museum told me the population can get down to as low as 15 people in winter.  Just 15 people!  They had a little library with a cardboard sign taped up.  A trivia night that—we quickly surmised—was fiercely competitive among regulars.  Just so many little things that charmed us.  We will definitely return.  

But, then, you have to imagine this place in the winter, how those lone 15 people see it.

The fact that these islands can really only be enjoyed by cruisers for a few months out of the year, I feel, makes them all the more special and attractive during the summer months. We enjoyed our weekend at Cuttyhunk, but it was soon time to leave that cozy mooring ball with our sights set on Martha’s Vineyard, a port that had evolved into a coveted destination for us that summer after many (many!) cruisers told us how lovely it was and that it was their favorite New England port.  Challenge accepted.  We had to sail there and experience it ourselves to find out.  

Making Happy, Chappy Memories at Martha’s Vineyard

While each of the New England ports Phillip and I visited last summer brimmed with hydrangeas of every color, Martha’s Vineyard positively overflowed with them.  I couldn’t stop taking photos of these fluffy pastel masterpieces we saw everywhere we went.  They also make incredible backdrops for selfies.  Doesn’t life among hydrangeas just look more enjoyable?  I know I will look forward to seeing and soaking up these exquisite flowers every time we do New England for the summer.  

But, that’s simply the flora and fauna.  Martha’s Vineyard also offered incredible shopping (Phillip and I found some really unique galley pieces and post cards and trinkets to send home to friends and family).  I discovered one of my now favorite photographers at the Untameable Gallery.  

Phillip ate the best cauliflower (yes, cauliflower) Reuben at Rosewater Market.  

Edgartown is filled with exceptional restaurants and bars overlooking the harbor.  

The mooring field on the inside is also rather large and easy to navigate.  But, we anchored on the outside with just as much ease and comfort and the dinghy ride in is quite exciting with the notorious car ferry (featured in JAWS!) going back and forth from Martha’s Vineyard to Chappaquiddick every 5-10 minutes.

Ashore, the streets of Martha’s Vineyard look like scenes straight out of a child’s storybook.  I kept thinking little blonde-headed children were going to walk up to me and introduce themselves as Hansel and Gretel.  

Phillip and I also took the bus one day to the island to spend the day in awe of the multicolored Oak Bluffs and stone-strewn shoreline (that’s a tongue-twister) on the north northeast shore of MV.  We saw a few other things while we were there that I don’t think I’m at liberty to mention on such a public platform …   Those of you who know MV, get it.  In all, it was a wildly fun day for the eyes and a glorious day at the beach, albeit a different kind of beach than we’re used to, but beautiful in its own unique right.  

I believe if I were to ask Phillip, however, he would say he holds the same memory from Martha’s Vineyard as his fondest—our day with Frank.  Phillip and I had run into another boat (this happens frequently when so many cruisers are visiting the same ports all summer), Jamie and Sheryl on Pacific High at Martha’s Vineyard with whom we had buddied up with in Ft. Lauderdale and other ports.  Jamie, Sheryl, and their crew and Phillip and I decided to go out for drinks ashore in Edgartown one evening and we ran into this lovely man, Frank, and his dog at the Behind the Bookstore bar.  Frank is a long-time local of Chappaquiddick and he regaled us all night with tales and stories that brought the history of the island to life which included, naturally, the Ted Kennedy scandal.  Having now seen the distance Ted ran and the channel he swam while that poor woman was drowning in the car he wrecked was heartbreaking and haunting but it did add to the rich allure of both islands.  

Frank’s stories, however, told of island life during the dreary winter months and how the locals that stick around pass the time: “Alcohol and books, more alcohol and firewood.  Don’t burn the books,” Frank said.  He was a hoot.  After a few crazy hours over drinks, the man was crazy enough to invite the five of us to Chappaquiddick the following day where he offered to chauffer us around and provide us with a personal tour of an island he has watched grow and change for forty years.  We did not regret the decision to take him up on it.  It was fascinating to see Chappaquiddick from a local’s perspective, understand the growth and changes, and get some scoop on the sly celebrities that have purchased homes there: Spike Lee, David Letterman, Carly Simon, James Taylor, and Diane Sawyer to name a few.  

Frank ended the tour with drinks and snacks that he served up for us himself at his home there in Chappaquiddick.  Overall, it was such a hospitable tour and a unique memory to take away from the island.  Martha’s Vineyard—and hopefully a reunion gathering with Frank—will be high on our list this coming summer!