We tucked in to escape the wind enroute to Nantucket for one night, and we stayed for 5. ❤️ Fell in love with Cuttyhunk, MA. August 29 – September 3, 2018


Gotta love these bumper stickers on a local golf cart. Adore both places! 

Cuttyhunk is one of the Elizabeth Islands, off the coast of Massachusetts, tucked in between Buzzard’s Bay and Vineyard Sound. There are a total of 8 islands, and all but Cuttyhunk and Peniskese are privately owned by the Forbes family of Boston. Forbes earned his fortune in railroads and international trade.  Beautiful, pristine beaches.  Charming weather-worn shingled homes. Lovely people. Peaceful. Total escape. Delicious seafood.  Enough said!  And, it’s an easy 3 1/2 hour cruise from Newport.

We went to Cuttyhunk based on a recommendation from Peter aboard Blue Star at Liberty Landing. It’s the perfect spot to break up the trip from Newport to Nantucket. The day we left Newport was pretty windy, so we decided to stop, as the winds were predicted to pick up over the next few days. We spent the first two nights in a slip at the town marina, then grabbed a mooring ball ahead of the Labor Day crowds. We were thinking about moving, but quickly realized how fortunate we were to have such a beautiful spot for the busy holiday weekend, and decided to stay put.  ❤️ Best thing about boat life is when you’re not working, you’re exploring or doing nothing, just enjoying where you are. Watching the boat traffic was entertaining! Yes, we’re boat nerds.

Everything on Cuttyhunk is accessible by foot, dinghy or bicycle.  There are few cars, and lots of golf carts, driven by the 30 year round residents. You have beautiful views of Martha’s Vineyard, and some of the other Elizabeth Islands, but don’t plan on provisioning in Cuttyhunk. You will, however, eat quite well!

While there are few places to dine out, but your options are pretty amazing!  The small wharf includes several little food shacks, one that opens mid-afternoon to take orders for lobster dinners. You come pick it up at a specified time, and take it back to the boat, or eat at one of the picnic tables on the dock, with a gorgeous sunset view.  Hmmm….not that the view from the boat is bad, but the dock view was pretty awesome, and it was a shorter walk after picking up our order, plus we got the sunset straight on!  The lobster dinner was delicious, and reasonable:  $35.00 each.

Rob was really happy that there was an ice cream shack next door to the lobster shack. How convenient!  While their flavor selection is limited, it’s good ice cream and the portions are very generous, served by the friendly staff!


Then there’s the Raw Bar.  LOVE the Raw Bar.  Their staff will wander the docks late in the afternoon to take your order, or you can place it at another little shack on the wharf,  and they’ll deliver it to your boat at your specified time.  20180829_172845

The adorable Parker delivering shrimp and oysters to the boat. He was excited to share that he had spent the morning digging up the oysters he was delivering!

When you’re in the mooring field, Raw Bar comes around in a boat, shucking oysters and clams, ladling chowder into containers, dancing, and just having a great time, along with all of their customers!  And, the food is absolutely delicious! Just call them on channel 72 on your VHF or flag them down and you’re set!

There’s Parker again!!

Further down the wharf, there’s a small bakery with delicious cinnamon buns, slathered in icing, served warm.  Delicious and decadent!

If you’re craving coffee, you’ll find a coffee shop next to the bakery.  It opens early and it’s a local hang out every morning!


One of the things we have missed about New Jersey this summer is the incredible produce.  So, we were thrilled to find the back of a golf cart in the wharf parking lot filled with corn 🌽, which was delicious!


We unfolded the bikes, and went out to explore. Up the hill from the wharf is a small “intersection”. On the corner is a small shop that sells t-shirts and keepsakes, and a short distance down the street to the left is a small shack that sells ladies clothes.  It’s open only when they feel like being open!  If you continue down that road, take a left at the T intersection, and you’ll head towards the ferry dock, and abandoned Coast Guard Station.

If you turn right at the T intersection, you’ll come to the Cuttyhunk Fishermans Club. Beautifully set on a hill overlooking Vineyard Sound and Martha’s Vineyard, they are known for their breakfast on the patio, and friendly, cheerful staff of college kids.  Those kids can also be found helping out at the ice cream, raw bar and bakery shacks on the wharf!

Cuttyhunk  Fisherman’s Club

If you continue up the hill from the wharf, you’ll come to the highest point on the island with beautiful views of Martha’s Vineyard.  There’s no picture  of that view, as it was unfortunately foggy and overcast when we were up there!  It was still a beautiful view of Cuttyhunk.


20180830_0752351Someone on Cuttyhunk has a sense of humor!

Once the fog lifted on our second day, the weather was spectacular!  We moved to the mooring field just before the Labor Day rush, dropped the dinghy in the water and explored the island from the water.  As we headed out of the harbor to a quiet beach near the inlet, we noticed numerous large, dark objects on the beach of nearby Naushon Island.  We went over to explore, and found these guys, lounging on the beach and in the water.  While the Forbes family was known for their stock of Merino sheep on the island, there is no mention of these animals.  Wildebeast seemed good until we learned that they are water buffalo.

We were thrilled to have the inlet beach to ourselves before the crowds arrived.  The beach is sandy with small, smooth rocks along the shore.  The inlet cut offers a rocky contrast just around the bend.

As it was Labor Day weekend, the marina and mooring field were full, with two yacht club groups and lots of friends cruising together.  It was bustling!

Across the harbor is a narrow spit of land with a dirt road.  If you follow the road up the hill it will lead you to a quiet secluded neighborhood of lovely homes.  Across the road is a spectacular rocky beach.


Before you enter the harbor, you’ll pass the ferry dock, which runs back and forth to New Bedford, MA.  There seems to be a sizable group that commutes to New Bedford daily, along with island visitors.  When visitors leave, it is island tradition to gather at the ferry dock to bid them farewell, and after the ferry leaves, they all jump in the water shouting farewells and waving their arms.  It’s a hoot, and they do it every single time a ferry leaves!

To commemorate the last night of the summer season, Cuttyhunk treated us all to a great fireworks display over the harbor.

Goodnight, Cuttyhunk!  Thanks for 5 fabulous days!


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