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How to Do Nantucket All Year Round

We’ve got the skinny on which ferry to book, the chowder to try, and the hotel room to stay in (it comes with a personal BMW).

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Welcome to paradise, 30 miles out to sea. Known by frequenters as ACK (the airport call letters), the Rock, and the Grey Lady on foggy days, Nantucket is one of the most illustrious islands in the U.S. It was settled by indigenous peoples centuries ago, and was later the backdrop of a thriving whaling industry in the 1600s—and the setting of Melville's Moby Dick. Nowadays, it's known as few things: a super-luxe vacation destination for one-percenters; an idyllic location for a second house (or a yacht); a hot spot for art, museums, and amazing cuisine; and home sweet home for many well-established locals.

While I grew up spending summers with family friends in Quidnet—often considered the "boonies," but personally my favorite part of the island—there's something for everyone among the sand dunes and chowder houses. You’ll find a smattering of it all on the island: world-class elite, celebrities, locals who have been around for decades, sea-worn ship captains, college kids working at the golf clubs and restaurants and yacht clubs in the summers. It’s a small island (roughly 14 miles long), but you’ll be surprised that it’s not just about yachting and billion-dollar homes (though there is a fair amount of that). Between the history, the buzzy restaurant and bar scene, and the pristine beaches that encircle the  island, Nantucket is a blissful coastal getaway, a breeding ground for the halycon days—all year long.

If you like a side of homemade ice cream, really fresh seafood, and elegant beach town bars with your vacation, then Nantucket is the place for you.

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How to Get There

Ferry

If you want to be old-school about it, which I recommend for first-timers, the Steamship Authority slow ferry is the way to go (also, if you plan to bring your car out to the island, it’s the only way to go). Many folks enjoy the leisurely 2.5-hour ride; you can grab a coffee and a snack, read a book, and in the summer it’s especially nice to stretch out on the top deck benches under the sun. Steamship also has a fast ferry (one hour) as does Hy-Line Cruises. Both companies operate out of Hyannis on Cape Cod.

Plane

Nantucket Airport may have more private jets than commercial planes on the runway but that doesn’t mean it isn’t accessible to those who want to fly. CapeAir and JetBlue both fly regularly to the island from New York (JFK) and Boston.

Where to Stay

Courtesy The Wauwinet

The Wauwinet: Known as the creme de la creme of hotels on island, and an American Express Fine Hotels & Resorts property, the Wauwinet is located on the northeast shore of the island (it's a good 25-minute drive from town) in—you guessed it—Wauwinet. This Relais & Chateaux hotel snags some of the very best seaside views on island, and happens to be home to one of the best restaurants, TOPPERS. Consider these accommodations the ultimate luxurious retreat this far out into the Atlantic.

Courtesy The Wauwinet

Just a short drive from the Wauwinet, you'll discover Sconset, the only part of the island considered its own township. Sconset is all white picket fences, gardens bursting with vibrant hydrangeas, and ivy-covered, shingled cottages. Be sure to head here for a sandwich at Claudette's (I always opt for the meatloaf), a scoop of ice cream from the market, and check out the Bluff Walk for sweeping (albeit windy) views of seals diving in the chilly Atlantic waves.

Courtesy White Elephant

White Elephant Nantucket: With several lodging options around town, the White Elephant is an excellent place to be if you want to be right near all the action, but still in a place that has an undeniably intimate feel about it. There are five types of accommodations owned by the hotel, but I recommend booking the three-bedroom residence that sits at the edge of town; the interior decor is understated and the beds are some of the comfiest I've ever slept in. Plus, it comes with your own BMW for cruising around the island, which is really, really fun.

Courtesy White Elephant

If you're interested in staying on other parts of the island (maybe out near Madaket for an excellent sunset, Surf Side for some great beach time, or mid-island for the convenience), there are plenty of Airbnb options. But be warned: they book up quickly, especially in the high seasons and during Daffy Festival and Christmas Stroll.

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Summer

Ah high, season on Nantucket. The 82 miles of coastline on the little island is nearly entirely open to the public, which means choosing a beach can be difficult—but there’s something for everyone. If you’re traveling with the family, Children’s Beach, Dionis, and Steps are nice options, as they face the milder surf on the sound-side of the island. And speaking of surf, there’s plenty of that on the ocean side. Surfside and Cisco are popular with surfboarders, and Nobadeer is almost always where you’ll find the party.

Something that's perhaps unexpected? There is an abundance of terrific sandwiches on Nantucket. Depending on where you are, you can pick up an overstuffed sandwich at Something Natural (near Steps Beach), Provisions or Fresh (both in town near the wharf), or Claudette’s (in Sconset). My personal favorite is the Bangkok chicken wrap and Cook's Cafe. You can pop next door to rent a jeep after lunch, too. 

If you like beer, wine, or spirits, you simply cannot miss Cisco Brewers. Located out near Cisco Beach and Barlett's Farm (another one for the bucket list, especially if you like an elevated farmers market) the Brewery is home to some of the best beer in New England. In high season, expect long lines and sometimes even a cover charge, but there's typically live music, food trucks and fresh oysters, and a darn good time. The best part: Cisco Brewery is open 365 days a year.

Perhaps you fancy a round of golf after a long day of sand, surf, and sips—head to Miacomet Golf Course for a beautiful 18 holes. Follow that with dinner in town, somewhere right on the wharf where you can watch the boats come in, like CRU or Straight Wharf. If you want to get out to the edge of town, try evening cocktails and dinner at Galley Beach

Of course, don't pass up ice cream at the Juice Bar after dinner. And if you fancy a nightcap, a good time is always had at the recently renovated Club Car, located at the bottom of Main Street in town. It's always my first choice, but be warned—there's usually quite a crowd (and a whole lot of singing) as soon as the pianist comes out to play. It's a real hoot, though if you want something a little more intimate, opt for a cocktail at Town.

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Fall

Those in-the-know are partial to this beautiful shoulder season—it's my personal favorite. In September, the days are still warm, and the Atlantic hasn’t cooled down yet, so it’s a great time to swim. School has started so most vacationers have left the island, meaning that there is far less traffic, but still enough people for it to feel a little buzzy. I love to take long walks on the beach this time of year (maybe head out to Quidnet or Madaket for this), grab a brew at Cisco Brewers, and spend some time shopping in town. A few must-see shops include Vis-a-Vis, the Skinny Dip, Murray's, Nantucket Bookworks, East End Gallery, Hepburn, and Milly & Grace.

There's also nothing better than snuggling up in a cozy sweater when the temperature cools in the evening and digging into some delicious, fresh seafood. Head to Nautilus for some shared plates, like the best blue crab fried rice of your life (seriously, this is coming from a Maryland native), dandan noodles, and an inspired cocktail menu. If you want something simple and truly authentic, wander just outside of town to Sayle's Seafood where you'll find (in my humble opinion) the best chowder and fried bay scallops in New England.

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Winter

Nantucket in the wintertime, known to many as the season of Stroll (we’ll get to that in a moment), is just as charming as you’d imagine a pint-sized northeastern island to be this time of year. The town is at its quietest for most of the cold season, but it's perfect if you want a restful getaway and some seriously stunning views. There's something really magical about the way the island looks in the winter; windswept and frosty, all hues of sand and blue. Winter is a perfect time to hunker down in town, eat out at year-round restaurants like Queequeg's and Ventuno, and maybe tuck into the town library for a good read. Be sure to check out the Bean for a hot cuppa on those cold days.

Aside from window shopping and bundled-up beach walks, the Christmas Stroll is the major event of the season on Nantucket. For one weekend in early December each year, the island bursts back to life to celebrate the holidays. Thousands flock out to the island as bars, restaurants, and stores reopen for a few days to welcome in the holiday cheer. There is, of course, a holiday parade in town, Santa does in fact make an appearance, and there are plenty of Christmas-themed events for little ones and adults.

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Spring

Spring brings with it wind, rain, the tease of warm weather, and the legendary Daffy Festival. Held at the end of each April, this festival a weekend of events that celebrate the coming of springtime and life back on the island. Things begin to thaw out, flowers are blooming, and the locals are preparing for summer again. You can expect picnics, an antique car parade, flower shows, and lots of vibrant yellow outfits—but it's up there in popularity with Figawi Race Weekend, the Fourth of July, and Stroll, so be sure to book accommodations, tickets, and reservations early on.

For five days every May, the annual Nantucket Wine Festival returns to the island, bringing several thousand wine-lovers and a full schedule of tastings, seminars, and wine-paired menus.

If you choose to come out during the spring, but avoid the major festivals and events, you'll find the island much quieter than summer, yet still perfect for a relaxing coastal vacation. Spend time wandering the streets, getting in and out of museums with ease (the Whaling Museum is a must-see for first-timers), and even having the beach to yourself—although it will be a tad too chilly for non-wetsuit swimming until mid-June or so.