Summer Sailing – Cape Cod – Martha’s Vineyard & Nantucket

July. We thought the weather had warmed up sufficiently to head north to New England – Martha’s Vineyard, Nantucket, Cape Cod and then Maine. We were warned there may be quite a bit of fog. Did we listen? No. We forged ahead.

In this post, there are 5 main journey sections.

  1. Sailing to Martha’s Vineyard
  2. Hanging out in Martha’s and Nantucket

Sailing Cape May NJ to Martha’s Vineyard


After transiting the Delaware Bay, we turned the corner in the Atlantic Ocean, and made a quick overnight stop in Cape May NJ. We anchored in front of the Coast Guard Station – a small anchorage for only a few boats, however there was heavy pleasure boat traffic in the channel, as it was Fourth of July weekend. Cape May is a go-to beach resort and cottage area for NJ, but seems to be better explored from land, or from the bay side of the bridge.

We left at daybreak the next morning to catch the best wind for our next 36 hour sail.


We had a good sail for these 36-hours albeit a bit rough. We had following seas, but they were in the 8-10’ range and a short dominant period. We sailed fast with the parasailor but by evening the wind was too strong for that sail through the night. So, we doused the parasailor and put up the main and genoa.

Not as smooth sailing, and not as fast, but safe. Note when we had the parasailor, we saw up to 23 knots TWS and were making 10-11 knots SOG. Very fast. We snagged a lobster trap in our rudder during this trip, but were able to remove it AND save the lobster pot gear for the fisherman.

By morning we lost wind velocity, speed, and direction. We were originally heading to Nantucket to make the trip east to west, Nantucket to Newport. But with the change in wind, we changed our destination to Martha’s Vineyard. This would dramatically change our overall trip plans since we’re now going west to east, Martha’s Vineyard to Nantucket. But that’s what sailing is all about. Arrived Martha’s Vineyard – 6 pm – perfect timing.

Summer Sailing in Cape Cod – Martha’s Vineyard, Nantucket


Arrival Menemsha Marthas’ Vineyard July 3, 2023 6 PM

July 4 we spent exploring the little fishing village / summer destination for the more adventurous Marthas Vineyard tourists. Menemsha is the city where they filmed much of the movie JAWS. Real people. Real fishing life. With a few good restaurants thrown in for the summer visitors. And the BEST fresh seafood shops around including harpooned Big Eye tuna. No anchorage inside for our size vessel, so good thing we had calm weather and did fine right outside the harbor for 2 nights. July 4th celebration fireworks could be heard all around us.

July 5 we decided to go see Gay Head Lighthouse – also called Aquinnah cliffs. In order to get there, we took the dinghy to the back of Menemsha pond, where we met the seafood farming folks, then tied up to a mooring, hiked about 1/3 the way there, and hitchhiked the rest of the way. Two kind ladies picked us up – on their way to a hippie commune – no joke.

The lighthouse was in danger of falling into the ocean due to erosion so has been moved back from the cliffs. Then we hitchhiked back to our boat.

This time a summer visitor with 2 kids in back picked us up! We can only imagine what the kids shared at the dinner table that night!

July 6, we departed for Vineyard Haven, Martha’s Vineyard. There are certainly some beautiful sailing tour boats around – full of people. We hung about on the boat quite a bit here, people watching. We toured an old military hospital converted to museum – where the most interesting part was the gardens. We enjoyed the beautiful homes on the coasts, saw the most unique dinghy in the world, and of course had to visit Black Dog Cafe. Very busy harbor with multiple ferries day and night.  

July 9 we visited Edgartown, Martha’s Vineyard. We took a ferry and rode bikes on the infamous Chapaquiddick bridge that Ted Kennedy drove his car off, killing his passenger Mary Jo, and ruining his chances for Presidency. (now sporting new guard rails). We spent the afternoon at the rocky beach looking over water shrouded in fog – not exactly my idea of a beach day.

Edgartown was a beautiful town with plenty of coves and inlets with beaches, many gorgeous large sailing vessels, old ship captain’s mansions, and summer cottages.

On to Nantucket 3 1/2 hour sail – and yes again in the fog. Very good inlet but strong tidal currents to get in. The area truly caters to boaters – massive mooring field with over 125 balls supporting up to 85’ in length, full of mostly local boats. This is where people keep their boats because there’s nowhere on land to keep them, little access to boat launches and sparse marina facilities. Numerous very large motor yachts 100’ or more were Med tied to the Marina.

The only available anchorage is small due to depth and in the middle of the current and the path to the Coskata-Coatue wildlife refuge. We became part of the tour of charter and pleasure boats transiting to the refuge. Very strong currents in the anchorage so dinghy deployment is best done on the tide change. Plenty of dinghy docks but often crowded – including children crabbing off the docks.

Nantucket was the nicest New England town we saw in these islands. Very rich in history and beauty. The homes, streets and grounds were beautiful and well maintained. Many MORE old ship captain’s homes, each one more beautiful than the next. We saw people in sport coats, slacks, and dresses in the evenings even on their boats.