Cruising Southern New England: Home Waters

A family of four enjoys 10 blissful days of cruising the harbors of southern New England

“Something tells me that you didn’t get that boat just to make a grand entrance at Block Island.”

That’s what my boss at the time said when I told him that Green, my husband, and I bought a boat to live and cruise aboard. I think he feared that I was about to turn in my notice and head over the horizon from our home port of Newport, Rhode Island.

Alas, nearly four years later, as I looked around the harbor from our mooring in Newport, his words rang in my ears as an ironic reproach. Although lovely, Block Island, a 25-mile sail away, was as far as we’d made it yet aboard Lyra, our Reliance 44 ketch. With the summer waning, we were staring into the face of another winter aboard with no real summer cruising under our keel. This wouldn’t do.


To be fair, these last few years have been busy — new baby, new jobs, a new business — and we’ve done plenty of daysails and weekend jaunts, but we were understandably getting itchy feet. So Green and I formed a plan. Getting away during the height of the summer is difficult for us, since Green’s profession as a daysail charter captain keeps him busy, so we decided on a late-in- the-season two-week cruise to Maine — a lofty goal.

One truth about modern families is that clearing everyone’s schedule for two weeks is difficult at best, and such is the case with us. Two weeks were whittled down to 10 days, and suddenly the planets would have to align if we were actually going to make it to Maine and back. But we didn’t give up, and we even lined up Green’s mom, Troid, to join us for the adventure and to lend a hand with the kids, Caitlin, 7, and Juliana, 2, for the passage to Maine.

As it turned out, the planets didn’t get my message. Fortunately, we had a backup plan. A benefit to our not having gotten much past Narragansett Bay is that the rest of southern New England’s cruising grounds are still new to us and can easily occupy us for 10 days.


Dutch Island

We left Newport in our wake, finally, and sailed around the southern end of Conanicut Island, peeked out at the sloppy conditions outside the bay, and decided to head up the West Passage to anchor off Dutch Island for the first night. One of the best things about cruising New England, in my book anyway, is the sunsets, and this night’s was stunning. After a hike early the next morning around the island, which once had a Dutch West India Company trading post on it, we were ready to head out.

Block Island


The plan for Day Two was to head directly for Cuttyhunk, the last in Massachusetts’ Elizabeth Islands chain; however, the seas were still quite bumpy, and the wind was just right for Block Island. Perhaps it was time for yet another grand entrance.

During the heat of the summer, Block Island is a busy place, and the wide, protected anchorage and mooring field, accessed through a narrow channel, is chockablock with hundreds of boats. Sailing during the late season, however, offers a more laid-back experience. The beaches surrounding Block Island’s Great Salt Pond are a magical place for kids, and the girls spent hours exploring the tidal pools.



After an entire day of moseying about Block Island, we finally made tracks to Cuttyhunk. The day started wet, cold, foggy and windless — providing an opportunity for us to tune the radar and warm up the diesel — but fortunately it changed to warm sunshine and light breezes. And that’s just how it goes in New England. It seems as though the temperature on any given day can vary by 20 degrees or more. When the breeze filled in, we enjoyed some of the best sailing on our trip. Green — who loves any opportunity to experiment with the sail plan — set up the mizzen staysail, and we easily gained a knot.

We’re a family that’s always on the go, but once under way, we had a chance to settle into the cruising rhythm. Someone once told me that the perfect age to go sailing with your kids is when they learn how to read. Now I see the wisdom in that. Our second-grader, Caitlin, will curl up with just about any book she can get her hands on. Juliana requires more parental interaction. Much more. While Green and I are hardly cruising neophytes, we’re new to the cruising-with-toddler thing. My mother-in-law, who raised two kids aboard and knows a thing or two in this area, proved invaluable. Could we have done the journey alone? Sure.

Would it have been as fun and relaxing? No way.

The entrance into Cuttyhunk is a little daunting — a narrow channel with rocky beaches on either side, lots of current, shifting sand — and the small harbor doesn’t offer much wiggle room. Indeed, watching other boats anchor here is a popular amusement. But this place is so worth it. The surroundings are idyllic, the tiny town is welcoming, and the hike up to the top of the island offers great views of Vineyard Sound and Buzzards Bay. My girls also found the island’s still-operating one-room schoolhouse to be a very cool spot.

Martha’s Vineyard

After leaving Cuttyhunk, we thought that it’d be fun to spend a day exploring Martha’s Vineyard, which requires sailing from Buzzards Bay through a pass between the islands to Vineyard Sound. These passes, such as Quicks Hole, between Nashawena and Pasque islands, have a shocking amount of current, so we did our best to synchronize our forays with slack tide.

Once in Vineyard Sound, we had a speedy sail to Vineyard Haven, where we anchored in the lee of West Chop. Since the forecast called for benign southeasterlies for the next day or so, this wasn’t a bad place to be; however, if the wind clocked to the north, we’d be completely exposed.

Martha’s Vineyard is the quintessential American summer getaway, yet we found it to be very accessible and even affordable for visiting sailors. With our sights set on a full day ashore, we got an early start, tied the tender to the dinghy dock next to the ferry terminal, and found coffee and breakfast sandwiches a short walk away. The island has an excellent bus system, which made exploring easy. We left tracks from Edgartown at one end all the way to Aquinnah and the Gay Head cliffs at the other. Juliana loves lighthouses, so we paid admission to climb to the top of the Gay Head Light.

Traveling by sailboat truly makes you appreciate distances, and it felt like we’d come a long way, so I’ll admit to feeling a tiny bit disheartened that I could see the top of Newport’s Claiborne Pell Bridge from the lighthouse. Ah, well.

Woods Hole and Hadley Harbor

At this point, we were well into our cruising New England voyage and had really adjusted to its rhythms. Unfortunately, we knew that our time was running out, and as much as I love the late summer in New England, the weather isn’t quite as settled as it is during July and early August. With the wind switching to a northerly, we knew we needed to head somewhere else, so we set a course for Hadley Harbor.

Hadley Harbor is located just west of the Buzzards Bay entrance to Woods Hole, and the surrounding land is privately owned by the Forbes family, so this isn’t the place for shoreside adventures. But Hadley offers something else to the visiting sailor: peace and solitude. On the day that we arrived here, the wind was still ripping on the sound and the current through Woods Hole resembled rapids, but tucked away in pondlike Hadley, you wouldn’t know it.

The next morning, Green and I took the girls for a dinghy ride to the town of Woods Hole, home of the eponymous oceanographic institute. A difference in traveling with kids — and I definitely consider this a benefit — is that even though we grown-ups would be quite content to relax on the boat with a book all day, the kids are looking for more things to do and have energy to burn. This leads us to explore places a little deeper in search of playgrounds and museums, and our dinghy ride to town was in search of the Woods Hole Science Aquarium, a very cool place that’s free to the public. In the summer months, you can also take a tour of the institute’s docks and restricted areas to learn about the research that’s performed here.

Home Again

With our weather forecasted to deteriorate, we started making plans to get back to Newport. Our long-awaited summer cruise was coming to an end, although it felt like it was just starting. After leaving Woods Hole, we sailed down Buzzards Bay and stopped in again at Cuttyhunk, but this time we stayed aboard. The next morning, we made our way back to Newport in cloudy and breezy conditions. A screaming sail up Narragansett Bay topped it all off, and then we were back on our mooring. Ten days may not seem like much, and compared to many other adventures, it’s not. But you don’t need a circumnavigation or an open-ended cruise to reap the benefits of this life, and indeed, even though we never made it to Maine, we got exactly what we wanted. Grand entrances and all.

Recommended Guides

For sailors unfamiliar with this area, New England can seem a tricky cruising ground, so good guides are key. Take a look at A Cruising Guide to the New England Coast by Robert C. Duncan, Roger S. Duncan, Paul W. Fenn and W. Wallace Fenn ($50; 2002; W.W. Norton & Co.),_ Dozier’s Waterway Guide Northern 2013_ ($40; 2013; Dozier’s Waterway Guide), Embassy Cruising Guide: New England Coast (10th edition, $45; Maptech), and A Visual Cruising Guide to the Southern New England Coast by James Bildner ($40; 2009; International Marine), and you’ll ply these waters like a local.

Harbor at Cuttyhunk

Siren, a New York 32, sails into the picturesque harbor at Cuttyhunk, which lies at the tip of Massachusetts’ Elizabeth Islands. Jen Brett
_Lyra_, a classic Reliance 44, rests at anchor off Block Island.
Lyra, a classic Reliance 44, rests at anchor off Block Island. Jen Brett
Sunset off Dutch Island, RI
During our 10 days exploring coastal New England, the girls enjoyed plenty of one-on-one time with grandma. This sunset off Dutch Island was definitely a favorite. Jen Brett
Troid, Green, Caitlin, Jen and Juliana Brett take in the view from Martha’s Vineyard’s Gay Head Cliffs