Whether you go for a dental confab or just to get off the mainland and kick back, summertime in Nantucket is every bit as idyllic as you likely imagine. BY LEISE TRUEBLOOD

THERE ONCE WAS a dentist from Nantucket . . . but we’ll stop right there, shall we? For there’s much more to this little island off Massachusetts than just a bawdy old limerick. Famed gray-shingled cottages, for one. Delectable seafood, for another. And, this June, a big dental seminar was held, quite fittingly, at the local Great Harbor Yacht Club. Yes, Nantucket is a ritzy summer getaway. Its roots, though, are far simpler.


British explorers discovered Nantucket in 1602, then later deeded it to a young merchant named Thomas Mayhew. When Mayhew decided to sell the island to its first settlers, his asking price was 30 pounds and two beaver hats. As that settlement took shape, so did the first stirrings of the oil industry, and the right whales in Nantucket’s waters were ideal prey. The whale-oil trade died out in the 1850s, but not before the island served as the setting for a little-known work of cetacean fiction called Moby-Dick.

Today, of course, this wee blot of land (some 48 square miles) is far busier. Yet simple charms abound. Cars are permitted on the island, but you’re better off relying on Uber, bicycle and your own two legs.

If you’re coming here from the Boston area, book your ferry ticket at steamshipauthority.com. (You can also fly into Nantucket Memorial Airport, inspiration for the setting of the popular 1990s sitcom Wings.) You’ll need a place to stay; try the B&B 21 Broad (21 Broad St.). This newly renovated boutique hotel is situated in the heart of Nantucket Town and offers an outdoor patio and fire pit, a steam room and a complimentary iPad for use during your stay.

Just down the street is Nantucket’s newest hotel, the cozy yet stylish Greydon House (17 Broad St.). Opened in the spring of 2017, this updated twist on a New England inn features bespoke luxury furnishings and a spectacular restaurant helmed by executive chef Marcus Gleadow-Ware (of Michelin-starred Aureole in Manhattan). Book reservations yesterday.

If you’d prefer your lodging with a heaping helping of Nantucket culture, try the White Elephant Hotel & Resort (50 Easton St.), a vast edifice with a full spa, chic suites of all sizes and an unparalleled location on the harbor.

Ready to sink your teeth into tasty things? Kick it all off with oysters and rosé at Cru (1 Straight Wharf), then stroll up Main Street to the recently redone Club Car (1 Main St.). There you’ll tuck into Baja-style tacos, pickled-eggplant toast and delicious Gulf shrimp. For dessert—brush afterward, but you know that—stuff your face with homemade ice cream and fresh waffle cones at The Juice Bar (12 Broad St.). The line might be out the door; the treats are out of this world.

For a postprandial drink and a good time, check out the infamous Chicken Box (16 Daves St.). It’s known for live music, and on any given night at this self-described “unpretentious roadhouse” you might see a local ’90s cover band—or Jimmy Buffett. Leave the kids (and the inhibitions) back at the B&B, and ask the bartender for a “Life Is Good” cocktail. Trust us.

If rest n’ relaxation, not rock n’ roll, is your preferred R&R, Nantucket’s beaches will do nicely. Jetties Beach is perfect if you’re here with the family. This sprawling oceanfront has a playground, a gift shop and a restaurant, all just minutes from town. Surfers should hie to Surfside Beach on the island’s south side, a paradise for wave lovers, where you’ll often spot seals hanging ten in the water beside you.

Après-beach, find your way to Cisco Brewery (5 Bartlett Farm Rd.). Don’t be fooled by the name; kids are more than welcome at this indoor-outdoor spot featuring food trucks, live music and locally made beverages. The dental seminar runs Wednesday through Friday; stay through the weekend and visit Brant Point Lighthouse (Easton St.), an iconic welcoming beacon at the entrance to Nantucket’s harbor. If it rains, the Nantucket Whaling Museum (13 Broad St.) is a great spot for history buffs, Melville aficionados and younger children alike.

All good things must eventually end, of course, and as you’re packing up for the return ferry, stifle your tears and pick up an island memento or two. Women should check out Erica Wilson (25 Main St.) for the founder’s curated clothing collections and beautiful needlepoint kits; the gents can find their treasure at The Haul Over (7 Salem St.)—think Patagonia and Yeti coolers. Don’t forget the famous color known as Nantucket Red, either: Get the signature hue on everything from ties to toiletry kits at Murray’s Troggery Shop (62 Main St.).

One last to-do before you return to the mainland and all those patients and appointments: Grab a bike and ride out some 40 minutes to the quaint, quintessentially Nantucket village of Siasconset (known by the locals as ’Sconset). Loop around this small town at your own pace to take in the sight of picturesque hydrangeas covering those famed cottages’ gray shingles. Pick up a light bite to eat at Sconset Cafe (8 Main St. in Sciasonset) for the ride home. With the wind in your hair, the sun at your back and, er, the snack on your teeth, you’ll find those simple charms from one end to the other of this beautiful little limerick-inspiring isle. •

LEISE TRUEBLOOD is an assistant editor at Nantucket Magazine.