Cuttyhunk, Penikese and a Comfortable Cruise Aboard the Grand Banks 32

Onne and Tenley van der Wal traded their 1972 Pearson 36 sailboat for Snow Goose, a 1986 Grand Banks 32 trawler, largely because they were tired of slogging along at 4 knots on long upwind passages. The couple prefers the relaxed pace of the Elizabeth Islands—small, quiet outposts off the coast of Massachusetts—but getting there under sail could turn a short trip into a full day’s work. “It’s 20 miles,” Onne says. “But on the Goose, it only takes about 2 hours and 20 minutes.”

Penikese has stunning natural beauty and is a great place for a walk. Photo by Onne van der Wal

Last September they left Jamestown, Rhode Island, around 2 p.m. to meet fellow members of the Conanicut Yacht Club for a weekend on Cuttyhunk. The motor up Narragansett Bay and across Buzzards Bay was civilized: Tenley settled with pillows and a book on the cabin settee while Onne alternated between the flybridge and the lower helm as the autopilot kept the Grand Banks on course at about 8 knots. Onne photographed birds and cloudscapes from the flybridge, then went below for tea or a snack while keeping an eye on traffic from the lower station. “It’s so civilized,” he says of traveling by trawler.

The van der Wals planned to rendezvous with friends Aidan and Kate Petrie, who cruise an Eastbay 38. Because the Eastbay is faster, the two boats usually travel independently and meet at the destination. Approaching Cuttyhunk from the west, the van der Wals passed over the island and left Penikese to port, then turned hard right into the inlet that leads to the well-protected Cuttyhunk Pond. The harbor offers roughly 50 transient slips and multiple moorings; Onne prefers tying to one of the pilings near the dock. Although September rarely requires reservations, he made one anyway.

By 5 p.m. the boats were secured. Without davits yet, Onne had to tow the dinghy from Jamestown and use Snow Goose’s boom to lower the 9.9-hp Tohatsu engine and dink into the water. With the islands’ sit-down restaurants closed for the season, Onne picked up Aidan for dinner aboard the Grand Banks. “We were pretty beat,” he recalls.

On Saturday morning the trio set out for Penikese Island in the dinghy. With three aboard they couldn’t plane, so the half-hour crossing was leisurely—perfect under blue skies and calm seas. Penikese, a 75-acre island with a quiet, little-known history, drew them ashore to walk and explore.

Penikese has a layered past. Bartholomew Gosnold was the first recorded European visitor in 1602. In the 19th century the Anderson School of Natural History briefly put the island on the scientific map and contributed to the Nature Study Movement. Later, in 1905, the state opened a leprosy colony there; the facility was controversial and eventually closed in 1921 after tragic outcomes and the demolition of its buildings. For decades the island stood mostly uninhabited until it hosted a school for troubled boys from 1973 to 2011, and later an opioid-treatment program. Since 2019 the Penikese Island School has used the remaining structures for youth camps and nature outings.

The island’s natural resources are the highlight today: eelgrass meadows in the surrounding shallows support fish and shellfish, while grassy hills and rocky beaches provide critical nesting habitat for seabirds, including the endangered roseate tern. With no one else ashore, the trio walked Penikese end to end in about two hours. “I’d never been to Penikese before,” Tenley says. “It has stunning natural beauty. Just a nice morning’s walk.”

Back aboard Snow Goose they made lunch and took a swim, then joined Conanicut Yacht Club members ashore for a classic Cuttyhunk lobster boil hosted by Cuttyhunk Shellfish Farms. Giant cauldrons of lobster, clams and corn were paired with beer and cornbread in a simple, convivial setting. Later they listened to live music at the church—a folk singer with a bass player—part of an artists-in-residence program that brings young creatives to the island to stay in an historic house.

They’d planned to return to Jamestown on Sunday, but a weather front kept them another day. The extra time meant coffee and donuts at the Cuttyhunk Café and a trip to the Cuttyhunk Island Market for supplies. Cuttyhunk’s small-town vibe—no cars, just golf carts and friendly faces—made for easy island strolling. Tenley notes a local tradition: when the last ferry departs for the day, some people take a running leap off the dock.

On Monday they set off for Jamestown despite a 25-knot west wind and an opposing tide in Buzzards Bay. The trip proved bumpy and Tenley became uneasy. Onne considered turning back but continued, knowing conditions should ease as they progressed. By Sakonnet Point things improved, and by the Brenton Reef and Castle Hill the water was glassy. “When we saw Castle Hill, we said, ‘man, we live in a beautiful place,’” Onne says.

Cuttyhunk remains a favorite destination for the van der Wals. “It feels like Maine,” Onne says. “It’s quiet. It’s just far enough, and if you pick your day and time, it’s a very peaceful place.”

This article was originally published in the May 2022 issue.