A sailboat on the water off the Nantucket coast.
Roland Bello

Besides its easily accessed beaches, great New England cuisine, and rich history, Nantucket is about as comfortable a place as you can find to bring the kids. 

Jesse Ashlock
February 14, 2018

As a kid growing up on the West Coast, Nantucket was one of those totems, along with historic liberal-arts colleges, fall foliage, and lobster rolls, of a WASP lifestyle I viewed with deep if slightly wary fascination. (And, of course, it figured into a few dirty limericks I learned.) I wound up going to a historic liberal-arts college in Connecticut, and have done more than my share of leaf-peeping and lobster-roll-eating, but I never did find my way to Nantucket until I’d really grown up — I mean, gotten married and had kids. And while I’m sure I would have had a blast on the famous island south of Cape Cod if I’d visited when I was younger, I can’t say enough about the experience of going with your family for a long weekend. It feels like what the place was made for.

That starts with the flight. For the last few years, JetBlue has been offering direct flights from New York, where we live, that take just over an hour — a breeze compared to the West Coast flights we’re used to. You arrive at the tiny airport — covered, naturally, with the same unpainted cedar shingles you see everywhere you go in town — and instantly you feel yourself downshifting to a slower pace, a more intimate scale, a weekend frame of mind. A Nantucket Island Resorts was waiting to load up my brood — me, my wife, our 3-year-old daughter, and our 1-year-old son — and take us to our residence at White Elephant Village (residences from $195; more during high season; open April through October): a roomy two-bedroom, two-bathroom cottage suite set among gardens, with a porch and a washer and dryer and its own front and back entrances. When we unpacked, we realized we’d forgotten the kids’ toiletries, but it was no problem. The property provided us with all-natural, hypoallergenic products from Dolphin Organics. This is the kind of service you so deeply appreciate when you’re traveling with small kids.

We’d come for Labor Day weekend, and while the weather was by no means hot, it was certainly warm enough to use the pool, where we found a treasure chest of noodles, kick boards, and miscellaneous floaties. One parent would hang out with the kids as they test-drove the pool toys while the other lounged on a deck chair under an umbrella, actually getting to reach a few snatches of a novel. White Elephant also has red Radio Flyer wagons available to borrow, which we did, carting the kids to the nearby Children’s Beach — yes, Nantucket actually has one, just outside town, that is dedicated for use by little people.

Further along the Nantucket Harbor from the Children’s Beach, toward the famous Brant Point Lighthouse, is the White Elephant Hotel (doubles from $195; more during high season; open April through October), where you’ll find the Brant Point Grill (entrées $32-$69). We headed there our first night, were seated on the generous covered deck, fastened our lobster bibs, and ordered martinis and the surf and turf for two. There was a game of cornhole set up on the lawn, and when the kids got bored and fully they ran into the gloaming to toss beanbags with the children of other diners as dusk gathered over the boats anchored in the harbor.

Besides the lighthouse, the other worthwhile waterfront destination in close proximity to White Elephant Village is Jetties Beach. It doesn’t look like much as you approach, but then you get over the dunes and find yourself looking at a a perfect New England beach: a wide, protected expanse of fine sand, with still water dotted by white sails beyond. There’s a clubhouse at the back of the beach called Sandbar (open May-September). We didn’t go in, but the sounds emanating from it were straight-up Margaritaville.

The pool at White Elephant Village.
Jeff Allen/Courtesy of Nantucket Island Resorts

In the other direction from the beach and the lighthouse are the almost too-perfect, sloped cobblestone streets of the town of Nantucket itself. Two mornings in a row we went to breakfast at Fog Island Café (entrées $10-$17), a low-slung, high-volume, slightly claustrophobic New England diner of the sort I fell in love with in college and will frequent until the day I die. It serves great huevos rancheros and a number of excellent riffs on Eggs Benedict. As we waited one of those mornings a slightly older girl asked my little girl if she wanted to play hide and seek.

Near Fog Island on Broad Street is the Sunken Ship, a wonderful modern-day general store that’s worth poking your head in even if you don’t need anything. We did need something — a purple shovel, something my daughter had been asking for since New York, and they had an excellent one, with a long wooden handle. Across the street is the Nantucket Whaling Museum, which everyone will tell you is a must-visit, and rightly so. Housed in a historic 19th-century candle factory, it offers a remarkably engaging account of the history of whaling on the island. There’s a widow’s walk with great views of the harbor, and a lovely children’s room with windows facing Broad Street that feels almost like a little maritime-focused Montessori school.

Everywhere we went with the kids, we felt welcome. At the Charlie Noble (entrées $24-$36), a recently opened seafood-focused restaurant on South Water Street, our waitress asked after seating us, “Would you like one box of crayons or two?” Nantucket Bookworks, on Broad Street, has recently added an adorable and impressively well-stocked children’s nook (with a kids’-sized entrance that requires adults to duck under) beside a vintage soda fountain.

Inside the Nantucket Whaling Museum.
Ellen Creager/Detroit Free Press/Getty Images

Besides the whaling museum, the other place it is mandatory to visit in the village is Murray’s Toggery Shop, the island’s premier purveyor (since 1945) of WASP fashions. We popped in on a damp day that carried the first true hint of fall to gawk at their amazing array of clothing in Nantucket red, the dusty-rose shade that has become synonymous with New England preppy style. My wife and I thought about buying some Nantucket-red apparel, but couldn’t quite bring ourselves to go there. I did, however, buy a shawl-collared wool Ralph Lauren cardigan at half off that instantly became a wardrobe staple.

Probably the most adult-feeling thing we did was to take the free island shuttle to the White Elephant’s sister property, the Wauwinet (doubles from $195; more during high season; open April through October), a charming harborfront inn on a skinny isthmus on Nantucket’s eastern end. There, we ate upscale, regionally focused prix-fixe meal on the casual patio of Topper’s (prix-fixe menu $80), the hotel’s fine-dining restaurant. There were other families there, but the vibe, especially inside in the intimate dining room, felt a bit more see-and-be-seen.

The Wauwinet Inn.
Jeff Allen/Courtesy of Nantucket Island Resorts

I was certainly aware during my visit of the more grown-up side of the island — seeing the early line form at the Nautilus (small plates $12-$24; entées $23-$38) one of the city’s hottest restaurants, around the corner from the Fog Island Café, or passing the Dreamland Theater, which a few weeks later would be a central hub of the Nantucket Project, the island’s wildly popular annual thought conference. There’s also the family-with-older-kids way of doing Nantucket: everyone on bikes, heading out to more remote beaches to go snorkeling or fishing. Those versions of the Nantucket experience, of course, are ones we can have too when we return to the island — again and again and again.

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