A Weekend with the Grey Lady

Nantucket is one of my favorite places on Earth and I don't make that distinction lightly. From the buzzy anticipation you feel when pulling in on the ferry to the cobblestone streets to the grey shingled cottages covered in hydrangeas, there's an unexplained magic on the island. Set like a jagged jewel in the Atlantic less than 30 miles off Cape Cod, the island packs an incredible amount of charm into its nearly 50 square miles.

While Nantucket was once the whaling capital of the world, its bread and butter has been tourism for more than a century, and the island is booming with amazing shops and chic restaurants. Now I'm hardly a local, and have only been on island a handful of times, but below are some of my favorite ways to experience this perfect place.

First things first, actually getting to and from the island is tricky due to the lack of bridges connecting Nantucket to the mainland. You can arrive either by air (there are direct flights from Boston, New York City and Washington, D.C., and 15-minute shuttle flights from Hyannis, Mass.) or by sea (the Steamship Authority or the Hyline offer regular service from Hyannis). Take a taxi from the airport (the boats dock in town) to historic Nantucket Town, where you’ll find the majority of the island’s restaurants, shops and bars.

Where to stay? Well, given the size of the island, there aren't an overwhelming amount of hotels but those that are there, are fantastic. The White Elephant is a show-stopper with luxury waterfront accommodations, suites and cottages, all with beautiful views of the harbor. It's expensive but, you knew this trip wasn't going to be cheap. We opted to rent a house out on Madaket Beach through Vacasa, a property booking site similar to Airbnb or Home Away. On the far Western side of Nantucket, it required some Uber's back and forth to town, but the crashing waves in our backyard were 100% worth it.

As you can imagine, the dining scene is phenomenal, even the casual side of it. Beaches mean picnics, and picnics, often, mean sandwiches. Something Natural is the heavyweight, here. The quaint shack of a sandwich shop, on an expansive property dotted with picnic tables, is famous for its home-baked breads. On that base, they construct towering sandwiches (a half will more than satisfy) from great deli meats and crisp veggies.

And while Nantucket has a number of solid ice cream spots, The Juice Bar dwarfs them all—in the scale of their servings, with fresh waffle cones that can easily hold three hefty scoops; and in the strength of their following. Forget a line out the door; on a warm summer evening, lines for the Juice Bar can stretch around two blocks. Go for old-fashioned creamery flavors like rum raisin, childhood classics like mint chocolate chip, or the only-in-New-England Grape Nuts ice cream. While Madaket is a bit of a trek, it’s worth it for Millie’s — a relaxed, beachy place with huge cocktails in mason jars; modern takes on tacos, po’ boys, lavish salads; and a sunset view for the books.

After grabbing a sandwich, ride your bike straight down Bartlett Farm Road to beat the late-afternoon rush at Cisco Brewery, Nantucket’s local beer maker, winery and distillery. Order a flight tasting, which gives you a shot-glass sampling of whatever beers are on tap. Order some oysters and littlenecks in the tented raw bar and then stake out a seat at a picnic table and soak in the live music and mellow crowd, which always includes a few children and dogs.

Shifting into dinner, which is generally more upscale, Straight Wharf Restaurant is pretty hard to beat. You’ll want to start off with the bluefish pate, a Nantucket staple; though everything’s enticing, it’s hard to pass up the Straight Wharf Clam Bake—buttered lobster with sweet corn, chorizo, potatoes, and littleneck clams. On Nantucket’s north shore, Galley Beach is a bit sceney, but indisputably beautiful—an open-air restaurant facing an expansive private beach and the glassy waters of the Nantucket Sound beyond.

For a nightcap, take a cab from the taxi stand at the bottom of Main Street to the Chicken Box, an island institution and a true summer dive-bar experience. Order a tequila shot and a beer (not a Martini).

And you can't leave the island without checking out one of the amazing beaches. With their tall seagrass and winding wood paths, every one of them will give you the quintessential New England beach experience.

  • Ladies Beach: Surf’s up! If you’re traveling with surfers, head to this beach when there’s swell. And dogs are welcome too—just remember to bring a leash.

  • Jetties Beach: When you’ve had enough salt and sun, head to the restaurant and bar Sandbar at the top of the beach and order their fried lobster and summertime frosé.

  • ‘Sconset Beach: Located just below Summer House, you can take a nap under one of their white umbrellas on this peaceful stretch of sand.

  • Steps Beach: The picturesque view of wooden staircases that leads you down to the ocean is not to be missed.

© 2017 by The Weekender.