Year-Round Fun on Nantucket

Uh-oh.

The two pups on the beach are so excited to see one another that they knock over the 6-year-old playing nearby, spewing sand everywhere in the process.
But mom Whitney Penrose doesn’t miss a beat, and her son Wyatt just grins.

No worries on this pup- and child-friendly beach on Nantucket, the famous island 30 miles off the coast of Massachusetts that is vacation heaven for kids—and pups alike. We stayed at Woof Cottage, in fact, right on the Boat Basin, a property especially accommodating to families with pooches. Our pup was not only greeted with a bed, treats and a new toy but also those manning the front desk offered to babysit her while we went to dinner. Check out the “Hot Dates Cool Rates” midweek deals.

Penrose, who lives in New Hampshire but is fortunate enough to have in-laws who live here, scans the beach—the pastel umbrellas dotting the stretch of white sand, the dunes just behind us, the older kids shrieking on their boogie boards while contented younger siblings build sand forts. Nearly half of Nantucket—the island is only 14 miles long and three-and-a-half miles wide—is preserved in its natural state with vast open spaces, salt marshes, and 52 miles of beaches accessible via free shuttle bus or bike. Visit Wheels, Heels and Pedals for info on all of the bike trails. {{{SmarterBuddy|align=left}}}”There are a lot of hidden treasures here,” says Penrose.

Come in September, adds her husband Coley when the crowds are gone, prices drop, and the weather couldn’t be better. Fewer than 10,000 people live here year-round but that can swell to as many as 50,000 in the summer.

Nantucket—the only place in America that has the same name for the island, the county, and the town—does have a well-deserved reputation for being preppy. “It is the only place you can wear pink pants and get away with it,” laughs Jim Genthner, who, along with his wife Sue, runs Endeavor Sailing Excursions, the oldest sailing charter on the island. And there are plenty of spectacular multimillion-dollar beach houses here, adding to the misconception that only the wealthy can afford to play here.

But while not cheap, Nantucket can also be a place for an affordable (especially in shoulder seasons like fall), laidback escape in beautiful environs with your choice of places to stay—a simple cottage with roses blooming in the yard, Jared Coffin’s historic whaling captain’s house, the deluxe White Elephant—and good eats. We had the best dinner we’d had in months at American Seasons, where Chef Michael LaScola showcases local ingredients and where his wife and partner, Orla Murphy-LaScola, says families with children are welcome. Some kids even enjoy the sophisticated menu as much their parents, she adds.

You’ll find every variety of food, from classic New England lobster rolls and chowder to burgers, sushi and Mexican, at Corazon del Mar. Local kids prefer A.K. Diamonds for pasta, pizza, fish tacos, and more. Your kids might also like the Crosswinds restaurant at the tiny airport where they can watch the small planes land and take off.

Be forewarned that Nantucket is the kind of place where you schlep your own chairs, umbrellas, picnic basket, and toys to the beach, but you can go to a different beach every day of your vacation. The youngest kids like Children’s Beach right in Nantucket town, the only town on the island, while Sue Genthner, who has raised two kids here, says parents might prefer Jetties Beach, which has a playground and a restaurant where you can sip a drink at sunset while the kids play in the sand. Check out the special Pirate Adventures for kids seven and under on the Endeavor.

You can safely let tweens and teens have more freedom than they might elsewhere, suggests Angela Raydnor, who has two teens and with her husband Seth owns three local restaurants. Tip for teens: Local kids gather on lower Broad Street called “the Strip” where there is great ice cream at The Juice Bar and a hot new store from London called Jack Wills. They also like Surfside Beach.

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Keep the kids busy all day with sailing, fishing, kayaking, surf lessons, theater programs at The Dreamland Theater (even for those with special needs), or simply chilling on the sand. Visit local Bartlett’s Farm. If it rains, go see The Sea Dogs! Exhibit at the Egan Maritime Institute, or teach the kids a little local history at The Whaling Museum with its hands-on discovery room. Read the local blog Mahon About Town to find out what’s going on.

We’ve arrived by ferry as most people do, though you can fly here too (Cape Air, JetBlue). We took the hour-long Steamship Authority Fast Ferry from Hyannis (Steamship Authority) and left our car there. Hy-Line Cruises also has ferries.

There are no traffic lights on the island and you may find having a car more of a hassle than it’s worth, especially poking around the narrow streets of Nantucket town. Instead, locals suggest you rent a Jeep for a day and explore. The entire island is a historic district. From the mid 1700s to the late 1800s, Nantucket was considered the whaling capital of the world where hundreds packed warehouses and made rope, candles, and sails. Moby Dick was set here, though Herman Melville didn’t visit here until well after the book was published.

Tourism now drives the island economy with special festivals stretching the traditional summer season such as the Nantucket Restaurant Week in late September and The Christmas Stroll the weekend after Thanksgiving when Santa arrives via Coast Guard vessel.

After a long walk to Jetties Beach—past one rose-covered, gray-shingled house after another—we end up at a local favorite, The Boarding House, for brunch. Our pup, Trooper, is tethered to the fence where everyone stops to pet her as she entertains the baby at the next table.

“Come back in September,” urges owner Angela Raydner. “There’s such a sense of well-being then.”

Sounds good to me.

Your Turn

What are some of your favorite activities on Nantucket? Are there other islands you enjoy visiting in the off-season? Share your thoughts by submitting a comment below!