Nantucket: No Jacket Required

Maureen Orth

Maureen Orth and Luke Russert share their favorite summer places on the laid-back island.

Nantucket has been our family’s summer destination since 1993, when Luke was eight years old. To some the island is EEE: elite, expensive, exclusive. But the Nantucket we love is more informal, more fun. Fourteen miles long and three and a half miles wide, it is nearly 50 percent under conservation protection, giving way for plenty of space to bike, walk the moors and, of course, feel the sand in between your toes on beautiful, often uncrowded beaches. Herewith, a few of our favorite places through which to enjoy Nantucket—without a blazer or stilettos.

Morning Fix

The Downyflake Restaurant (18 Sparks Ave.; 508-228-4533.)

Luke: Cherished by locals because it’s affordable and open ten months a year, The Downyflake, where breakfast starts, for the most part, at 6 a.m., serves bacon, eggs and toast with just the right amount of grease, whether you’re fueling up to go fishing or recovering from the night before.

Maureen: As a joke, Mark, the previous owner, used to stamp the outline of the Virgin Mary onto slices of bread to see if friends would notice... If you just want some doughnuts, Downyflake’s are the best in New England.

Dinner with a Detour

Millie’s (326 Madaket Rd.; 508-228-8435.)

Luke: Named after legendary Nantucketer “Madaket Millie” Jewett, this is the spot to watch the sunset. Owner Bo Blair and chef David Scribner take great pride in their menu of salads, tacos and po’boys. The food will leave you full and happy; throw in the relaxed Zac Brown Band–style vibe and the potent Madaket Mystery drinks and you’ll want to ditch the stuffy overpriced dinners elsewhere and go every night.

Maureen: On the way to Millie’s, stop at an almost hidden pier on the left, about four tenths of a mile after the town dump (which we affectionately call "Madaket Mall"), where, if you tie a piece of string around a raw chicken leg and drop it in the water, giant snapping turtles will rise up to grab the bait! It’s a must with kids.

Work off Lunch

The Summer House (Rooms start at $395; 17 Ocean Ave.; 508-257-4577.)

Luke: The inn is a favorite with Hollywood stars, and its restaurant boasts a giant piano bar. Its Summer House Beachside Bistro, directly across the road and down steep steps to the beach, is a great casual lunch spot—though not necessarily inexpensive. Ride a bike out to Sconset (Young’s Bicycle Shop [508-228-1151] will deliver anywhere), have a lobster roll and take in the ocean view. Sneak a dip in the pool before heading home.

Maureen: If you’re too pooped to bike back, Nantucket’s public Wave buses have bike racks on their fronts. Very thoughtful.

Classic Photo Op

Sankaty Head Lighthouse  (At the north end of Baxter Rd., off Polpis Rd.)

Maureen: Get your picture taken at this iconic landmark, which was relocated in 2007 to lessen the horrific nearby erosion eating away at the backyards of some of the island’s grandest houses.

Luke: Fun fact: Sankaty is one of the oldest still-operating lighthouses in the States.

On a Rainy Day—Or Not

Maureen: Head to the town’s center and visit Mitchell’s Book Corner (54 Main St.) and Nantucket Bookworks (25 Broad St.). Both are filled with terrific beach reads and beautiful books about Nantucket, including cookbooks. It’s lovely to browse in the old genteel tradition. Also, the Whaling Museum (13 Broad St.) has a fabulous collection of all things whale and whaling, as Nantucket was the world’s richest whaling outpost. It features a giant sperm whale skeleton at which to wonder. Across the street is The Juice Bar (12 Broad St.; 508-228-5799), with the island’s best ice cream.

On Saturday mornings, don’t miss Rafael Osona Auctions (21 Washington St.)—it’s free, lively entertainment to watch Rafael ply his trade as he deftly dispatches the contents of one island house, only to have its paintings, rugs, chinoiserie and furniture be deposited into another. Those little lightship basket purses with carvings on top that ladies carry sometimes have gone for as much as $12,000. Nearby, next to St. Mary’s Church, is the Sustainable Nantucket Farmers & Artisans Market. And, of course, there’s amazing shopping in town, but I don’t have the space to get into it here!

Maureen and Luke: A caveat—there are lots of places we love but couldn’t squeeze in. 

Bring the Boat Shoes

Slip 14  (14 Old South Wharf; 508-228-2033.)

Luke: The preferred watering hole for those working the yachts and sailboats docked in Nantucket Harbor, Slip 14 is also a good place to grab a just-caught seafood dinner while wearing a T-shirt. Eat at one of the outdoor tables and watch the boat culture pass by. It’s pretty packed on weekends, so plan ahead.

Maureen: You don’t have to wear a T-shirt, and yacht owners also occasionally darken its door. On Friday nights nearby local art galleries have openings. And if you walk over to Straight Wharf (Slip #1015; 508-228-5585), two minutes away, you can take the sloop Endeavor’s 90-minute sunset sail in Nantucket Sound.

Don’t Miss These Beaches

Luke: Nobadeer Beach—right by the airport—has been called “Bro-Ba-Deer” for its mostly younger, college-age crowd. [Maureen: If you are over 27, I’d avoid it.] The waves are decent, and if you drive down the beach far enough, it’s relatively peaceful. But if you want to meet people and socialize, hang out close to the entrance. Hellers Way near Cisco Beach is an undiscovered gem; I feel bad writing about it. Before you get all the way to Cisco, take a left on Hellers Way and drive to the end. There are miles of pristine beach and good waves.

Maureen: Fat Ladies Beach, out Miacomet way, has great waves, too. Sometimes you need four-wheel drive to access. And, no, you don’t see many fat ladies.

Luke: For anything surf-related, there’s ACK Surf School (Nobadeer Beach; 508-246-7872). Local island surfing legend Gaven Norton will have you standing on a longboard in no time. Pay him a visit; all ages are welcome.

After the Beach

Cisco Brewers (5 Bartlett Farm Rd.; 508-325-5929.)

Luke: So Apollo the sun god is not cooperating, or he’s cooperated too much and you’ve had your fill at nearby Cisco Beach—what to do? Head to Cisco Brewers. It’s dog-friendly, and what better way to escape than by drinking local craft beer, island-made vodka and wine [Maureen: They're not that bad!]—all while listening to live music in a funky courtyard?

Maureen: When you’ve had your fill of hairy legs in flip-flops, wander over to Bartlett’s Farm (33 Bartlett Farm Rd.), down the road, with its huge nursery and pricey local produce. I’ve seen Drew Barrymore at the yoga classes in its loft. Another charming farm is the Slosek family’s Moors End (40 Polpis Rd.), about one mile east of The Downyflake, where freshly picked lettuce awaits in an old-fashioned bathtub. The flowers are lovely, too.

Food Fight

Luke: I love the darkly lit Pazzo (130 Pleasant St.; 508-325-4500) for its Italian and Mediterranean fare and quality wine. [Maureen: Pazzo really seems Moroccan because of the delicious chicken served in a tagine. Luke: I checked with the owner: It’s definitely Italian.] It’s not pretentious, and it has some of the best service on the island. Call ahead, and try to go on a live-music night; if you can’t score a table, eat at the square-shaped bar—it’s probably even better.

Maureen: My most favorite place to have dinner at the bar is Fifty-Six Union (56 Union St.; 508-228-6135). It’s cozy, with an outstanding bowl of curried mussels.

Find True Love Here

The Chicken Box  (16 Dave St.; 508-228-9717.)

Luke: Jimmy Buffett told me the Box was his favorite bar in America. [Maureen: What a name-dropper! Luke: As I was saying...] I don’t disagree. The live-music dive has been the stuff of island legend for decades. Owners Rocky Fox, John Jordin and Packy Norton make sure you have an amazing time as soon as you come through the door and behold its large wraparound bar. My best friend met his wife here, so if you are looking for love, head on over! [Maureen: You might have to stay up all night to get lucky.] Arrive early to beat the crowds and stay till last call at 1 a.m.

Maureen: A girlfriend and I blew Luke’s best friend’s mind one Sunday when he came into the Box and discovered us having a beer at 3:30 p.m. A concerned call from Luke soon followed. I assured him that I wasn’t going to let Nantucket wreck the family’s reputation by living la vida loca.