Word of Mouth: Nantucket
Fall outdoor activities within the magical Massachusetts island

Those who have never been to Nantucket may be surprised to know that the word itself encompasses two locations: an entire enchanting island off the coast of Massachusetts and one of the towns therein. Known for pristine beaches, active marine life, cranberries, cobblestones, blankets of fog and boutiques, the isolated island casts a spell over visitors. Many do know of it as a tony summer destination, but our trip this fall revealed much more: quiet hikes along bluffs and beaches scattered with fisher-folk, sunset chasing on foot and garden cocktails in lounge chairs. And although the quaint cedar-shingled homes—and the magnificent Whaling Museum—may conjure up the past, the island’s food (and dessert) scene certainly represents the present day.
Ventuno
With so many acclaimed dining options in Nantucket, it can be challenging to decide upon one. After several recommendations, we found ourselves at the Italian eatery Ventuno, which occupies a large outdoor space along a side street. The environment was lively (though safe) and the food certainly exceeded expectation. Other spots worth checking out include The Proprietors (which has a strong cocktail program, too) and Cru (which has outdoor waterfront seating). Regardless of where you go, it’s wise to make a reservation (if possible).
The Juice Bar
It does not matter the time of year, if The Juice Bar is open, one must visit. As the name suggests, this venue—operating now through an ordering window—serves fruit and vegetable juice. More importantly, they sell dozens of superb ice cream flavors (we recommend Cake Batter) and their own homemade cones (and a cup-shaped cone in a container for those who prefer a neater experience).
TOPPER’S
TOPPER’S, a waterfront restaurant located within The Wauwinet Inn, is an island institution for a few reasons. As one would expect, its fine dining menu incorporates local and seasonal ingredients. Exemplary signature cocktails are on rotation—and there’s a lengthy wine list (1,550 bottles). It’s really, however, the ambiance that sets the restaurant apart. With reservations, a boat from the town of Nantucket will take diners to TOPPER’S. And the sprawling back lawn, complete with lounge chairs, welcomes guests well in advance, to sip drinks and nibble on hors d’oeuvres as the sun sets.
White Elephant
The White Elephant Nantucket embodies so many desirable attributes: it’s adjacent to the center of the town of Nantucket (a two-minute walk) but encompasses enough waterfront land that it feels quite far removed. Beautiful, spacious rooms and clean, friendly service couple to set it apart. And for those who visit Nantucket but do not stay here, we also highly recommend their Sunday brunch—an experience with a view that’s impossible to forget.
Hero image by David Graver
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