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Cruising Southern New England Waters

Brant Point lighthouse has welcomed thousands of sailors to Nantucket

Brant Point lighthouse has welcomed thousands of sailors to Nantucket

One of the most wonderful childhood vacations I can remember was back in 1971 when my best friend invited me to his family’s summer home on Nantucket Island. For a 10-year-old kid, this was a thrilling trip for many reasons, not the least of which was the fact it was also my first ride on a jet plane.

As you might imagine, Nantucket was relatively quiet and undeveloped back then; my two main activities were riding around the island on a bike I rented from Young’s Bicycle Shop and stopping in at the local candy store each day to buy a Broadway Roll, which is a strip of cherry licorice.


Forty-six years managed to slip by before I finally returned to Nantucket, this time via a sailboat I charted from Bareboat Sailing Charters ( in Newport, Rhode Island. The owner of the company, Brian Blank, is a Newport native who has been deeply involved in sailing his entire life. As such, he not only provided my crew and me with a fantastic boat but also gave me one of the most comprehensive and useful charter briefings I’ve ever heard.

Our trip coincided with the 2018 Newport-Bermuda Race, which meant my crew and I would be able to catch up with some other racing and sailing buddies who were in town for the event. Needless to say, we had a great night out on the town before we set sail.

Our plan was to head first to Martha’s Vineyard and then continue on to Nantucket and finally the small, relatively undeveloped island of Cuttyhunk. Something to keep in mind when sailing these waters is the currents. The combination of the area’s 3ft tides and many islands and passages can result in weird changes to your speed-over-ground. You also need to be mindful of lobster pots. It will not only ruin your day if a line gets caught in your prop, but there could be a significant fine associated with messing with a lobsterman’s livelihood.

As luck would have it, we were sailing just in advance of the main tourist season and didn’t expect to encounter quite the volume of people that Martha’s Vineyard and Nantucket typically attract in the dead of summer. We knew, though, that it would still be busy. To avoid having to fight for space in the popular harbors of Edgartown or Oak Bluffs on our first stop at Martha’s Vineyard, we planned to grab a mooring ball in the quieter town of Vineyard Haven: a part of greater Tisbury that was still a “dry” town until just recently, meaning it doesn’t yet have the big party scene of its neighbors.

The first part of the trip from Newport to Martha’s Vineyard took us along the East Passage over the Colregs demarcation line and into Rhode Island Sound, where we had pretty easy sailing, aside from keeping clear of a number of well-marked rocks and ledges. Things got a little trickier, though, as we entered Martha’s Vineyard Sound, where the current can be especially strong, and there are more shoals, rocks and lobster pots to avoid.

After picking up our mooring, half our crew hiked over to Oaks Bluffs, while the rest kicked back in Vineyard Haven. Then, the following morning, we regrouped and grabbed breakfast at the ArtCliff Diner (the best place in town to start your day) before renting bikes and heading out to Chappaquiddick Island to see the infamous bridge that Ted Kennedy drove off in 1969. This destination has some morbid connotations, as 28-year-old campaign strategist Mary Jo Kopechne was in the car with Kennedy and drowned in the incident. The event literally changed the course of American history, as it more or less squelched Ted Kennedy’s chances of running for president.

Martha’s Vineyard, with its extensive network of cycle paths, is a very bike-friendly island, and the local chamber of commerce in Tisbury has free bike maps and lots of good information regarding where to go and what to see. Some good options include West Tisbury Farmers Market, Alley’s Historic General Store, Martha’s Vineyard Glass Works and the Polly Hill Arboretum. For those looking for beach time, East Chop Drive or the West Chop Loop are also a fairly easy ride from downtown Tisbury. If, on the other hand, you want to stretch your legs, you can cycle out to the western end of the island and tour Lighthouse Road.

On the bike ride out to Chappaquiddick, we stopped at the Japanese-style Mytoi Gardens. Created in the 1950s by a local resident, this relatively small property has a wonderful little footpath that wanders though ornamental trees and shrubberies, separated by small ponds and footbridges with the occasional seat placed at convenient locations so you can sit and ponder life. A little further down the road from there, we reached our destination, Dike Bridge, where Kennedy drove off his 1967 Oldsmobile Delmont 88 into Poucha Pond. The bridge covers a span of 80ft over a narrow tidal river. Today, it looks much as it did in the ‘60s, except there’s now a guardrail. Interestingly, nowhere on any of the signage for the bridge do you see mention of the accident.

After that, it was time to head off to Nantucket Island, which also meant sailing through waters known for unpredictable storms, dense fog, strong currents and many dangerous shoals. More than 700 ships have run aground in these waters over the years, causing it to be called “Graveyard of the Atlantic.” The final channel into the Nantucket Harbor is especially tricky, as it is narrow and has a lot of boat traffic, so keep your eyes peeled and have a secondary watch on duty.

As we approached the island, it did not look drastically different from what I remembered. Sure, there were more large summer homes along the shore than there had been in 1971. However, in stark contrast to many other popular waterfront areas, I did not see rows of ridiculous McMansions or hideous high-rise hotels, due to the fact Nantucket has very strict zoning rules requiring that new homes resemble the island’s classic architecture. There is also a very strong preservation movement to save existing historic buildings, as well as a progressive system for protecting the island’s remaining tracts of undeveloped land—all thanks to a fellow by the name of Walter Beinecke Jr., a visionary who guided Nantucket along its long and arduous transition from whaling center to tourist town.

In fact, whaling and whale oil production began to decline in importance back when petroleum was first discovered in the United States in the mid-1800s, so that by the turn of the last century, Nantucket was a ghost town. Beinecke, however, saw a potential for tourism here, given its close proximity to Boston. He also, fortunately, did not want the island to turn into just another junky tourist destination. And thus began Nantucket’s unique and historic approach to development.

At Beinecke’s peak of influence in 1968, he controlled two of the island’s three gas stations, five inns, the majority of downtown stores and a sprawling landmass that he put into conservation. Beinecke eventually sold off most of his assets, a number of which—including the Boat Basin, the Jared Coffin House, and the White Elephant—are now owned by New England Development, which also owns the historic Wauwinet Inn. As a result, many of them have remained much the same over the years, with the exception being the Boat Basin, which now boasts a full-service marina, 240 slips and a wide array of waterfront cottages. Likely one of my favorite of the properties is the Wauwinet, which has been in operation since 1875 and is located just inside of the Coskata-Coatue Wildlife Refuge on the northeast corner of the island.

Once ashore, I was also glad to see that many of the other old landmarks I remembered were still standing, including the Whaling Museum, the Historical District and Young’s Bicycle Shop (first opened in 1931), where my friends and I rented bikes for a tour of the island, which included a visit to the town of Siasconset. On the way there, we also stopped at the Egan Maritime Shipwreck and Lifesaving Museum. As I said, the region is known for its shipwrecks, and the museum chronicles many of those disasters and also celebrates the bravery of the many islanders who risked their lives to save their fellow mariners. Be sure to take a tour with one of the experienced guides, as they add much to the experience that you won’t get just looking at the displays.

As for the quaint seaside town of Siasconset, it proved to be a great place to spend a quiet afternoon. It’s not only picture-postcard perfect with its historic charm and sleepy dirt roads, but has one of the best public beaches on the island.

A few hours after that, our bikes safely returned to Young’s, we headed out on a four-wheel-drive guided tour of the Coskata-Coatue Wildlife Refuge. This long arm of sand stretches from the eastern tip of Coatue Point to the Great Point Lighthouse on the northernmost corner of the island, and our trip took us along a beautiful sandy beach road north, replete with natural dunes and nesting sea birds, terminating at Great Point Lighthouse at lands end Nantucket. A nice break from the hustle and bustle of touristy downtown, the Coskata-Coatue Wildlife Refuge also gives you a chance to see what Nantucket might have looked like before man set foot on the island.

Later that same evening, we also stopped in at Topper’s Restaurant at the historic Wauwinet Inn. The views here are some of the best on the island—as is the food. Before we ate, we made sure to take out a few minutes and walk out onto the restaurant’s private secluded beach and watch the sunset over Wyers Point on Coatue.

The day after that we set out for the little island of Cuttyhunk. Because the island is only accessible via a couple of small taxi/ferry services out of New Bedford, it’s not very crowded and there is relatively little development. In fact, there really isn’t much of anything there at all, aside from a few scattered summer homes: which is also all part of its charm, a sleepy and peaceful place that provides a nice respite from all the action of Martha’s Vineyard and Nantucket. While there, we made a point of enjoying a great “locals” lunch at the Cuttyhunk Cafe, which offers freshly made donuts and lobster rolls.

Finally, if you ever choose to sail to these southern New England waters, be sure and check out Newport itself. This seaside city is, of course, one of prime sailing centers of the United States and has a multitude of interesting maritime museums and historic seafaring lore to explore. It is also a popular tourist destination, with a wide assortment of great restaurants, hotels and shops.

While there, I stayed at Gurney’s Newport Resort and Marina, which sits on its own island just north of downtown where it commands a great view of Fort Adams, the East Passage and Newport itself. It is also conveniently located close enough to town that you can still access all the action via water taxi or on foot at the same time it provides plenty of peace and quiet.

One of my favorite strolls in Newport is along the famed Cliff Walk, where some of American’s richest families built fantastic mansions at the turn of the century—most of which are now open for tours. Beyond that, the waters around Newport are, of course, a mecca for sailors of all stripes—not just those on charter—so that it would be hard to imagine a community more infused by the culture of the sea. I don’t know why it took me 46 years to get back there, but I’m glad I did. My only regret is I never found that old candy store and my Broadway Roll. 

Writer Eric Vohr also has a travel web site and blog at

July 2019



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