Arabella Grand Tour New England

Visiting Martha’s Vineyard, Nantucket and Cuttyhunk on the ASA Grand Tour of New England

By: Charter, Destinations, Event

Writer, Editor and Sailor, Bob Curley, is a Rhode Island Expert who contributes to American Sailing on sailing New England and the Caribbean.

The ASA Grand Tour of New England aboard the sailing yacht Arabella is highlighted by stops at three of the historic jewels of the Massachusetts coastal waters: Martha’s Vineyard, Nantucket, and Cuttyhunk Island. The first two are among the most treasured destinations in New England for sailors or anyone who wants to seek sophisticated solace by the sea, while the lesser-known Cuttyhunk offers a window into the past when isolated fishing communities pulled prosperity from the waters of the Atlantic.

Martha’s Vineyard

Arabella in Martha’s Vineyard

The Grand Tour includes two stops at Martha’s Vineyard, offering guests plenty of time to explore the 58 square miles, 19 beaches and communities large and small that comprise this popular summer colony for the elite. From the Arabella’s anchorage in the port at Edgartown it’s easy to charter a tour bus or rent a moped, bikes or even take a bus to explore the island. Popular destinations include Oak Bluffs, a community of beautiful Victorian era gingerbread houses, and a former Methodist religious camp full of charming cottages. On the other end of the island (and cultural spectrum) is the Aquinnah peninsula, where members of the Wampanoag tribe — who called this island Noepe, or “land between the waters” — still reside. Atop the multihued Aquinnah Cliffs stands the picturesque Gay Head Light, which has warned mariners away from rocky shoals since 1856. 

Bird watching, hiking and the beach are highlights of a visit to the Long Point Wildlife Refuge and the Felix Neck Wildlife Sanctuary; Chappaquiddick Island is home to the Cape Poge Wildlife Refuge, set on a barrier beach and renewed for its great fishing and views of the circa 19801 Cape Poge Lighthouse. Katama Beach offers the choice of leisurely sunbathing by a placid pond or challenging surfing on the Atlantic Ocean. Farms, a Japanese garden, an excellent historical museum, and the Farm Neck Golf Club are other ways to spend time outdoor on the Vineyard, not to mention al fresco dining at some of the island’s top restaurants, including the 19 Raw Oyster Bar in Edgartown and the Barn Bowl & Bistro in Oak Bluffs, which also has a bowling alley and sports bar.


Martha’s Vineyard and Nantucket seem to exist side-by-side in the mind’s eye, and while both have shared history in whaling and as summer retreats for the wealthy, subtle differences persist between these two islands. Crescent shaped and further out to sea, Nantucket is known for its ocean-cooled and sometimes foggy weather; smaller than Martha’s Vineyard, the island is also somehow more modest in its bearing: even some of the million-dollar homes here are clad in weather-resistant, unpainted shingles. 

Nantucket also embraces its status as the whaling capital of the world in the 19th century with a Whaling Museum in the heart of Nantucket Town. Modern “whale hunts” are far more benign, taking visitors out in search of humpback, minkes, and finbacks on whale watching tours. Seasonal shuttle buses help visitors get around the island, stopping at popular destinations like Surfside Beach and Siasconset, a.k.a. “Sconset,” a charming former fishing village that can also be reached via a pair of bike paths. Or just spent your time on island walking the cobblestoned streets of Nantucket Town, filled with boutique shops and restaurants, then settle into a seat on the patio at Cisco Brewers out on Bartlett Farm Road to sample local brews, get food truck grub, and listen to live music.


The remote Elizabeth Islands string westward from Wood’s Hole on Cape Cod, and the outermost of these is Cuttyhunk. Less than one square mile in size, the island saw some of the earliest English settlers in America step ashore in 1602, and comparatively little has changed in the intervening centuries compared to the Vineyard, Nantucket, and the Cape. Half of the island is a nature preserve full of wildflowers and coastal wildlife, and the sole community is the  town of Cuttyhunk, where most people get around by foot, bike, or golf cart. 

Lobster and clams in Cuttyhunk

Fishing remains one of the most popular activities on the island, particularly for striped bass; hiking trails lead to old World War 2 bunkers turned into picnic areas, and beaches are both beautiful and uncrowded. Just remember to bring your own food and especially drink: shopping choices on the island are limited (choices include a pizzeria, fish market and raw bar, and an ice cream parlor), and no alcohol is sold or served anywhere on Cuttyhunk. A bastion of small-town New England life, Cuttyhunk isn’t the Vineyard or the Cape, nor does it want to be. The town motto is “The Place to Do a Whole Lot of Nothing,” and indeed this is a great place to just unwind and get your feet in the sand for a few hours before continuing your voyage on the Arabella.

Bob Curley is a freelance travel and healthcare writer and editor based in Rhode Island. His books include 100 Things to Do in Rhode Island and the forthcoming 100 Things to Do in the Caribbean Before You Die. Learning to tie a proper Monkey Fist is on his personal bucket list.