Checklist: Nantucket, Massachusetts

Due to her frequent veil of clouds, Nantucket is euphemistically referred to as The Grey Lady. But the threat of gloomy gray weather doesn’t put off the many moneyed folks who have holiday and year-round homes on Nantucket. In fact, the new, less lyrical nickname for the Massachusetts island is “the billionaire’s playground.” For many visitors, Nantucket, which lies off Cape Cod and is Massachusetts’ southernmost town, is a place for sedate summer beach fun. During high season, the population can swell from around 10,000 to 50,000, making offseason months more desirable to discover the real island, not the touristy one. Offseason is cheaper, too, but during winter months, most hotels and many other businesses close. So unless you have a billionaire friend, a summer visit might be your best bet.

Whatever the season, the main hub of humanity is the town of Nantucket, whose cobblestoned center and 19th century red brick architecture recall an English market town. But the nearby Boat Basin and still-bustling harbor remind this is a seafaring community built on salt and sand, and whalebone and blubber.

1. The Hy-Line

Photo courtesy of Hy-Line Cruises

Getting to Nantucket isn’t easy, and if you want to take a car, it isn’t quick or cheap, either. Do yourself and Nantucket a favor and go carless; take the high-speed Hy-Line passenger ferry from Hyannis. It takes about an hour and you can make like a local and hunker down with a drink from the bar while skipping across the Nantucket Sound on what is basically public transport. Rather than a tourist, you already feel a part of the island life. Most hotels and resorts offer complimentary shuttles to and from the ferries. Hands down, the Hy-Line is the most fun way to get to Nantucket, the jaunt becoming part of the adventure.

2. Brotherhood of Thieves

How can you walk past a sign that declares Brotherhood of Thieves and depicts a horned gentleman and not walk in? There’s a touch of danger about the place, given the name; you almost feel you should knock to enter. The interior is suitably dark with black painted wood and brick, and low conspiratorial ceilings. But don’t be afraid, it really is just a bar and restaurant, with an outdoor patio for summer, and an upstairs with a more restaurant-y feel. The menu is casual. Order a piggybACK, which is Vermont-made WhistlePig rye whiskey aged for five months longer at the Brotherhood’s request. The name merges the distillery’s name, ACK for Nantucket (it’s the airport’s code), and “back” for how the bar likes to serve whiskey: neat with your choice of back. As for the bar’s name, Brotherhood of Thieves was the name of a locally written pamphlet, published by Stephen S. Foster in 1844, railing against slavery. Upon closer inspection, the horned one painted on the sign holds a bag of money in one hand and shackled slaves in the other.

3. Starlight Theatre & Cafe

Photo by Linda Clarke

This shingled, low-rise building located on North Union Street looks unlike any other cinema. Equal parts movie theater, restaurant, and bar, the Starlight Theatre & Cafe is indeed a newly renovated 90-seat theater with full digital screening. Though closed on Wednesdays, it is open year-round and shows first run flicks. Then there is the cafe, which serves eclectic comfort food like grilled asparagus with sautéed mushrooms, goat cheese, and a fried egg crostini; and grilled shrimp and super creamy cheesy grits cooked with smoky bacon. While blues and heartland rock murmur in the background, locals slug beer, wine, and signature cocktails with names like the Godfather (Jameson and amaretto) or the Union Street Mule (3 Olives vanilla vodka and ginger beer). The cafe’s cast iron pellet stove is to put to use in colder weather and during warm weather the adjacent patio bar opens up. In addition to the cinematic entertainment, local musicians often perform at Starlight, as well. A night at the Starlight really is living like a local.

4. The Whaling Museum

Make no bones about it—and that’s a pun that will be obvious later—Nantucket’s early success as a settlement came from the wanton pursuit of whaling. The Whaling Museum is not only a grim testament to the bygone trade in bone, blubber, and oil, but it also tells a kinder story of Nantucket’s long-term relationship with the sea and its creatures. The 46-foot sperm whale skeleton—there’s the pun—on display is a juvenile who washed up dead in 1998. But for once, the cause of death wasn’t human—it was a tooth infection. In a way, whales took some revenge on Nantucket’s townsfolk; the Great Fire in 1846, which destroyed much of the town, was fueled in part by whale oil, and it was a symbolic end to Nantucket’s whaling dominance.

5. Brunch at Breeze

Photo by Linda Clarke

Tucked inside the Nantucket Hotel—and spilling out onto the front porch, weather permitting—on Easton Street, a short walk from the Whaling Museum, Breeze Restaurant is a smart, but relaxed spot. It’s named after the original hotel, the Point Breeze, which opened in 1891 and was destroyed by fire. The Nantucket Hotel, a new building that opened in 2012, is named in honor of the Point Breeze’s neighbor, The Nantucket, which was the first grand hotel built on Nantucket, back in 1885. An antique fire truck sits outside ready to shuttle guests to and from the ferry.  While the land is historic, the menu is most certainly not. Come for brunch and sip on prosecco, or whatever tipple you fancy, and order from a very 21st century food selection that includes lemony avocado toast with poached eggs, lobster Benedict, and polenta topped with creamed wild mushrooms and bright cherry tomatoes.

6. Nantucket Looms

Photo by Linda Clarke

Nantucket Looms is filled with the coziest throws, blankets, and scarves ever made, and art from around 80 local artists. Upstairs, however, is the less visited studio where the master weavers work thread into those throws, signature Bretton style sweaters (plain or striped), and other covetable cuddly cloth goods. The studio reminds of the craftsmanship lost to the modern manufacturing of cheap, disposable goods. Since 1968, the Loom’s luxurious mohair, wool, cotton, silk, and cashmere goods have been embraced by the rich and famous. Jackie O was a customer and a framed hand-written letter from the former first lady graces the weaving studio’s wall of fame. Another framed note marks a swatch of tweedy fabric created especially for a revamp of Chanel’s HQ in Paris. Far from exclusive, this really is a cottage industry, employing around half a dozen local weavers, who work the wooden Maine-made looms, and create items to love for a lifetime.

7. Cisco Brewers

Photo cby Linda Clarke

Cisco Brewers was originally founded in 1981. As a sort of spin-off to Nantucket Vineyards and later, in the early 2000s, the Triple Eight Distillery was added. You can take a tour and do a tasting; there are three bars serving the flavorsome beers, wines, and spirits. If you’re lucky, you’ll be treated to some live music, too. You’d be remiss not to try the Grey Lady, a tasty wheat beer fermented with Belgian yeast and brewed with fresh fruit and spices, perfect in summer. How about a Notch whiskey (as in “not scotch” single malt whiskey) when the weather turns cold? Welcome spring with Triple Eight’s vodka made with organically grown corn and sand-filtered island water. Like the island, it’s a brewery (winery and distillery) for all seasons, and most tastes.

8. Nantucket Bike Tours

Photo courtesy of Nantucket Bike Tours

Getting around Nantucket isn’t difficult on foot, but only if you’re sticking to the downtown area, where everything is close. Most hotels and resorts offer courtesy shuttles and there are municipal buses, most of which are seasonal, however. If you want to explore the rest of this beautiful island unlimited, a bicycle is the way to go. This way you can bike out to places like the Sankaty Head Lighthouse, which dates back to 1850 and is located near the village of Siasconset on the eastern part of the island. Nantucket Bike Tours offers guided treks and rentals, and also a much-loved coffee shop, the Handlebar Café. Being small—around 47 square miles, give or take a bit of coastal erosion—Nantucket is the perfect biking vacation spot, and biking is perfect for it because it’s already crammed with cars, despite ordinances to limit them.

9. Galleries

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Photo courtesy of shopnantucketisland.com

Don’t forget, this is an arts colony and there are several tempting galleries, including Cavalier Gallery and G.S. Hill Gallery. For all your authentic Nantucket-inspired items, visit the G.S. Hill Gallery, which features one artist, G.S. Hill. The Nantucket resident creates paintings, prints and specialty gifts, all of which are displayed and sold in the gallery. You can also purchase the famed Nantucket Lightship Baskets from here, and Nantucket fresh water pearl jewelry by Pam Freitus of Pearlhill. For a little more refinement, Cavalier has a fine art and sculpture garden.

Linda Clarke is a freelance travel writer whose work has been published in the Boston Globe, New York Daily News, and several other print and online publications.