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.
For this author’s first-ever visit to Nantucket, we picked up a 2020 BMW M8 Gran Coupe in NYC, drove four hours to the port in Cape Cod and tucked into the Steamship Authority ferry for the two-hour water transfer. As someone who has driven (or been subject to the drive) from NYC to Hyannis, Massachusetts for more than two decades, this was the most pleasurable commute of them all.
“That’s a whole lotta car for little Nantucket island,” an eager admirer told us as we pulled off the boat. And yet, navigating the town of Nantucket’s tiny center and the greater island’s winding roads—to Siasconset, Madaket, Wauwinet and all that’s in between—contributed to the all-around joy of visiting the eight spots (though really more) that we’ve shared below. During our four-day experience, we went from cranberry bogs to three-course meals, and found that we would have happily stayed another four days.
For those of us who hanker for a quality cup of coffee even when on vacation, the town of Nantucket’s Handlebar Café (which has an order window and outdoor seating) is worth the visit. Not only is it easy to get to, the coffee (and matcha) is undeniably well-made—and that includes iced drinks, too. The menu also includes delicious pastries and cakes (though, if you are looking for something savory, head over to Provisions and snag “the original” breakfast sandwich).
The town of Nantucket is in no short supply of high-end boutiques, many from familiar brands. Nantucket Looms, however, has an important local history. It’s been in town since 1968 and their second floor is where looms are housed for use by the brand’s weavers. On site, they also produce fabrics for blankets, scares and kitchen accessories. Directly across the street, it’s worth swinging by Mitchell’s Book Corner for literature on the island, too.
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).
At the far western corner of Nantucket Island, Madaket Beach extends out toward the setting sun. For anyone interested in beach strolls beneath the setting sun, it’s a beautiful option (with parking nearby). Of course, there’s also the 14-mile round trip beach walk to Great Point Lighthouse, on the other side of the island. Though most prefer to rent a beach-battling vehicle for the experience, we walked—passing dozens of people fishing, plenty of seals and one shark. For anyone who loves spending time outdoors, we recommend both of these walks.
To visit Nantucket and not pass through Siasconset (colloquially known as Sconset) is a disservice. First, the petite village’s local diner, Claudette’s, is a necessary stop for coffee, pastries and sandwiches. Second, Sconset’s Bluff Walk is a trail that runs along cliffs and even through the backyards of some of the island’s most magnificent homes. It offers stunning views in all directions—be that through well-kept gardens or the ocean crashing below. (For anyone seeking a fourth walk, we recommend strolling through the Windswept Cranberry Bog and Stump Pong.)
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.
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