A version of this article was previously published by Fathom.

NANTUCKET, Massachusetts - Only 30 miles off the coast of Cape Cod, the tiny island of Nantucket has long been a favorite destination for travelers seeking a taste of quaint New England charm, beautiful white sand beaches, and excellent seafood restaurants. The island’s architecture, best known for its grey shingled structures, gives visitors a sense that not much has changed around the island since its whaling heyday when Nantucket was a center of commerce as well as a leisure destination. But a walk along the cobblestone streets of the main town (also called Nantucket) reveals that there is more than history and dust tucked between the red bricks of the stately mansions. World-class hotels, celebrated restaurants, high-end boutiques, and galleries have gracefully adapted to the quirky 18th- and 19th-century architecture, creating an eclectic community that gives visitors something new to explore year after year.

STAY

If you aren’t staying privately or renting a home, you’ll find a number of wonderful hotels with a range of accommodation. If you’re visiting during high season, book way in advance, as the island fills to capacity, despite the premium room rates.

White Elephant Resorts is a collection of properties dispersed throughout the island and town with accommodations in almost every category. Jared Coffin House, their only year-round property, is a stately mansion in town with 43 rooms spread across two buildings. Dating to the mid-19th century, the charming brick building recalls its history through the antique furniture in the common spaces, classically painted portraits of historic figures on the walls, and a lingering sense that this old lady has seen it all. The best rooms to book are the five newly renovated suites. And even if you’re not staying here, don’t leave the island without having a beer and a bowl of chowder in the refurbished basement Tap Room.

Jared Coffin House *(Photo Courtesy of Jared Coffin House)*

The Wauwinet, White Elephant’s premier property and the island’s only Relais & Chateaux hotel is located fifteen minutes by car from downtown on expansive acreage flanked by two private beaches. Originally opened in 1875, The Wauwinet is a romantic, adults-only retreat occupying a grand, gray shingled main lodge with 32 rooms and suites and three cottages. The stately property — note the large lawn, dock, and tennis courts — is also home to Topper’s restaurant, one of Nantucket’s finest. If you are looking to escape the crowds (and your kids), wrap yourself in luxury, or are seeking a romantic place to hold a wedding or special event, The Wauwinet is absolutely that place on Nantucket.

White Elephant, the anchor property of the group’s hotels, is the largest accommodation on the island, with a configuration for every kind of traveler. Located just three short blocks from town, the main hotel has a commanding location on the harbor. An institution of sorts, White Elephant has been hosting guests since the 1920s. A destination for families, this hotel has seen generations born, raised, and married on its lawn. In addition to the main hotel building, the offerings include garden cottages, Residences with one to three bedrooms, an inn with deluxe rooms and suites, lofts on Main Street (ideal for hosting private parties and events), and the Cottages at the Boat Basin, which sit right on the docks. White Elephant has a full service, on-site spa, and one of the only hotel swimming pools in town. Located within the Residences, the pool is available by reservation for hotel guests only. In addition, all White Elephant properties provide full concierge services, complementary bikes, beach towels, and chairs. Like I said: White Elephant can accommodate every type of guest. But it’s worth repeating: Be sure to book in advance.

Guest Suite at White Elephant *(Photo Courtesy of White Elephant).*

EAT

If you visit during high season, make dinner reservations well in advance, and be prepared to wait patiently for a table at the restaurants that don’t take reservations. Off season, check to make sure things are open, as many places close during the winter (and some as early as mid-September).

There seems to be no formula to Nantucket’s restaurant scene; many inhabit creaky, uneven spaces with an airy attitude of design that draws on the island’s nautical past, while others dim the lights and play to the dark and stormy nights that without a doubt come to Nantucket in winter.

Nantucket has many little spots that are great for coffee or a light breakfast. Our favorites were Born & Bread in town, Something Natural on the edge of town, and Roastd General Store out of town.

If you’re hungry for something a little more substantial, Black-Eyed Susan’s is known for having the best breakfast on the island. (No reservations, so come prepared. Seasonal only.) For a long boozy brunch, saddle up a bike and earn those calories with a ride out to The Wauwinet, where the lobster roll is one for the ages.

Come lunchtime, pub-style fare and everything that goes with it (burgers, beer, BBQ, and football) is easy to find, but the two best spots in town are The Rose & Crown and B-ACK Yard BBQ. After lunch, The Juice Bar on the wharf is everyone’s favorite place for ice cream and fresh-pressed juices.

When dinner beckons, Nantucket has amazing options both in town and farther afield. For refined Italian, book an intimate table sister restaurants Ventuno or Via Mare (located inside Greydon House Hotel). For pizza and good home-style Italian cooking, Pi Pizzeria out of town is a cozy place where locals flock.

Bar Yoshi and Cru, both down on the docks, serve excellent raw seafood, sushi, and shellfish. For a true New England-style, catch-of-the-day feast, seasonal Straight Wharf is somewhat of an institution. Finally, for a more farm-to-table experience, with fresh, locally sourced ingredients, Dune and The Proprietors Bar & Table are both lovely.

But our favorite meal in Nantucket was definitely at The Nautilus, a small, dimly lit space with an excellent bar and southeast Asian inspired dishes. They take reservations one week in advance.

WHAT TO DO

An authentic Nantucket experience must include exploring the island by bicycle. (It's nice that most hotels offer them to guests free of charge.) Be careful not to go down one-way-streets in the wrong direction — the locals disapprove — and stick to the 30 miles of paved bike paths when you can. If you are visiting Nantucket in the summer season, then you are definitely spending a lot of time at the beach. The best way to experience the sand and sea that surround this little island is to pack a picnic into the basket of your bike (Born & Bread is a great place to stock up on provisions) and head out on two wheels towards the sand. Everyone has an opinion about which beach is best, but you really can’t go wrong – it just depends how far you want to pedal.

If you aren’t into swimming and sun but still want to connect with the sea, take your bike for a short spin out of town to Brant Point Lighthouse, the second lighthouse built in America. For a longer jaunt, make your way out to Siasconset, “Sconset” to locals, for a picnic and walk along the bluff. Stop for provisions at Sconset Market, the seasonal community store that takes pride in selling fancy groceries, and find a path between the houses that leads towards the sea. You may think you are trespassing when the path winds through the back gardens of some of Nantucket’s finest mansions, but you’re not: The bluff paths are public space. A word to the wise: Avoid stopping at The Summer House. The has-been property in an amazing location is billed as a restaurant and inn, but has more of a dilapidated flophouse feel. (A sad state of affairs confirmed by chatting up the locals.) If you have come to Sconset on four wheels instead of two, make sure you have the number of a Nantucket cab driver, as it can be challenging to hire a ride back to town.

When you are tired of swimming, sunning, and biking, there is still plenty to do on Nantucket to stay busy. Eating, drinking, and shopping are very popular island pastimes that can keep any appetite occupied for a few days.

SHOP

If there is one thing to do on Nantucket, it’s shop. For everything and for everyone: from T-shirts and ball caps to needlepoint and ball gowns. Nantucket is home to brand name stores like Ralph Lauren, Faherty, Vineyard Vines, and The Black Dog (all of which are available online), but the real of fun of cruising the cobblestones is ducking into local shops that carry a wide range of small, obscure brands, as well as unique keepsakes and antiques.

For contemporary women’s clothes from little-known brands, drop into Dawn, The Skinny Dip, and Atlantic.

Looking for a pair of unique sandals? Clorinda Antinori has them in different styles and colors.

For menswear with that unique Nantucket-New England flair, head to Murray’s Toggery, where the entire back room is devoted to faded red trousers and shorts (the ultimate Nantucket look) and you can still pick up a striped rugby shirt (the kind I haven’t seen since the early 1990s).

Down the road is Erica Wilson, which sells a unique selection of women’s wear along with its namesake cotton pajamas and a whole section devoted to needlepoint (I was tempted). In that vein, pop into Nantucket Looms for handwoven textiles, blankets, and scarves — an island tradition for decades. Up the hill, Stoke ACK (ACK is Nantucket airport’s call sign) puts a Nantucket twist on skater and surfer wear.

If you are on island to engage in the serious sport of antiquing, start your search for folk art or the perfect vintage Nantucket basket at Sylvia Antiques, in business for 95 years and going strong.

When out walking around town, be sure to pop into the lovely galleries that are sprinkled throughout town. You will not only find a number of artists with standalone shops, but also outposts of larger galleries representing a wide variety of well-known and emerging artists.

DETAILS

One of the biggest challenges facing Nantucket is the shortage of people willing to work there. The work is largely seasonal with few days off, the cost of living is through the roof, and the conditions involve a churning bath of thankless tourists. Many employees come from the Caribbean; they move to warm-weather destinations in the north to work during the summer season. In conversation with locals, I learned that some employers subsidize employee housing, but not all. Despite this, everyone we met working in the service industry was friendly, kind, and welcoming. When you consider the cost of your trip and the fun that you are having, consider tipping generously, knowing that your funds get absorbed by a community of people who really do deserve it.

Nantucket is seriously expensive. (And given what's happening with the economy, prices will only keep going in one direction: up.) In high season, you will be hard-pressed to find a room or guest house for less than $500 per night. As someone remarked while I was there, the number of extremely wealthy visitors to Nantucket is a level above what the luxury travel industry experiences in other parts of the world. (Translation: Dropping five grand per night in August doesn’t bat eyelashes around here.) As a result, there are increasingly fewer options for budget travelers. Unless you plan to couch surf and subsist on $13 sandwiches from the walk-up window at Walter’s Deli (which are really good by the way; the address is 10 Broad St.), be prepared to pay to play.

Ferries make frequent crossings from Hyannis (1-2 hours, depending on the type of boat) and New York (seasonal). For those wishing to fly, Cape Air’s fleet of Cessnas connects to several airports on the mainland, primarily Boston Logan Airport. Various airlines offer seasonal (and more reliable) jet service between Nantucket and major cities on the eastern seaboard.

Warning: Nantucket becomes severely isolated when bad weather strikes. When the elements do not cooperate — fog in the summer, wind in the winter — planes and ferries are routinely grounded. It’s best to have some flexibility baked into your plans. I speak from experience! After three glorious days on Nantucket in early October, a nor’easter blew in, grounding ferries and cancelling flights. With a stroke of luck (though a day after our scheduled departure date), I was able to book two seats on the only jet to get out for days. Traveling home to the west coast, you can imagine how jolting this was, so a word to the wise: Sometimes the weather wins.

You really don’t need to rent a car if you plan to stay in town. Just know that taxi or Uber rides to the outer reaches of the island or a remote beach cost upwards of $20. (Still cheaper than renting a car.)

If you stay at The White Elephant, the hotel has a fleet of BMWs for the complementary and exclusive use of guests on a first-come, first-served basis (worth waking up for if you want to explore the island).

We visited Nantucket in early October when the leaves were just beginning to turn and the sky was a brilliant blue reflecting the coming of fall. The only downside of visiting at that time is that some restaurants and shops had already closed for the season, and the beach was more for blustery strolls than baking in a bikini.

During high summer, the island is packed (packed!) with people. If what you want is a quiet, sunny weekend away September is the ideal time to visit — the weather is still glorious but fewer people are crowding the cobbled streets. The second busiest time of year is the first weekend in December, when Nantucket hosts the annual Christmas Stroll. Main Street closes to street traffic, stores and restaurants are wide open, and people are invited to shop for gifts and socialize before the island nearly shuts completely for the long winter months.

Whats to Come:

ITALY ★ 9.2022

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