You’re strolling along the waterfront of an important early American port town admiring how the sunlight, diffused by an early morning fog, wraps the gray shingled buildings in a soft glow. Window boxes, overflowing with flowers and ivy, dress up homes once owned by sea captains. Here and there, an energetic bicyclist or jogger appears from around a corner. While you might be in any number of places along the New England coast, you sense something distinctive here, an island uniquely situated geographically—and historically. This is Nantucket.

Nantucket has a mystique and charm all its own. Just ask anyone who lives there or has ever visited this small “elbow of sand” (as novelist Herman Melville once called it) some 30 miles off the coast of Massachusetts.

The name Nantucket—which means “faraway land” in the island’s original Wampanoag language—suggested from the beginning a place apart and distinctive.

The first English settlers, who arrived in the mid-17th century, formed a community of farmers, sheepherders and fishermen. By the early 18th century, however, deep-sea whaling had become the island’s economic mainstay and the island’s whalers ventured as far away as the South Pacific. Nantucket, in fact, became the whaling capital of the world, providing the whale oil that lit homes and cities around the world. As Melville wrote in Moby Dick, “Thus have these Nantucketers … conquered the watery world like so many Alexanders.”

The island’s most prominent citizens were sea captains, traders and owners of factories that processed whale blubber and spermaceti, a prized oil that comes from the head of the sperm whale.

By the mid-19th century, however, whaling was in decline as cheaper petroleum replaced whale oil and the island’s harbor silted up. When gold was discovered in California, many Nantucket men left to seek their fortunes. The Civil War distracted others.

Enter tourism in the latter half of the 19th century, when summer visitors became the catalyst for Nantucket’s recovery. As a result, the island became—and remains to this day—one of the most popular destinations in the world because of its beaches and historic charm.

Exploring the Island

Small and easy to get around without a car, Nantucket offers something for everyone.

You’ll find cobblestone streets bordered by historic architecture (over 800 pre-Civil War buildings remain); beautiful natural scenery (50 percent of the island is protected); award-winning resorts and restaurants; and, one-of-a-kind shops, galleries and theaters. There’s also plenty of recreation— bicycling, beachcombing, swimming, surfing, boating, birdwatching, golf and tennis. Seasonal festivals celebrate wine, food, books, comedy, film and more. What you won’t find are stoplights, neon, and chain stores or restaurants.

Well-heeled residents invest in exclusive real estate and enjoy an active social scene. Nevertheless, the island’s vibe is casual and unpretentious. You’ll find welcoming people who go out of their way to be helpful.

The Whaling Museum, once a whale oil processing and candle factory, is a necessary first stop for first-time visitors, the place to get a quick overview of Nantucket’s history from the time of the earliest settlers to the whaling era. Displays include a 46-foot juvenile whale’s skeleton (an adult might be twice that size), portraits of sea captains, scrimshaw (carved on whalebone, of course), Nantucket’s iconic “lightship baskets” and much more.

The Whaling Museum’s parent, the Nantucket Historical Association (nha.org), offers walking tours of the town of Nantucket.

You’ll learn about the town’s pre-Civil War buildings and homes, including the early 19th-century brick mansions built by the Starbuck family. And you’ll hear stories about the island’s most famous residents, among them Benjamin Franklin’s mother; R.H. Macy, founder of the Macy’s department store; and astronomer Maria Mitchell, the first woman to be inducted into the American Academy of Arts and Sciences.

Nantucket Island Resorts
Nantucket Island Resorts has a portfolio of historic, luxurious accommodations and restaurants on the island.

Consider the White Elephant hotel, situated on the waterfront and just a short walk from the center of town. Originally the dream of a prominent 1920s Nantucket socialite, the hotel has been updated and expanded over the decades. Although much has changed since its humble beginnings, the property remains a prominent piece of Nantucket history.

The hotel offers the perfect base from which to explore the town’s museums, shops, restaurants and nightclubs. Alternatively, you can relax in a chaise on the lawn while overlooking Nantucket Harbor, rejuvenate in the on-property spa and even arrange a cruise on a Hinckley yacht stocked with wine, champagne and snacks. A family-friendly place, the hotel also has a “children’s beach” where parents can drop off their young ones for supervised activities, such as yoga, soccer, music and dance programs.

The White Elephant’s Brant Point Grill has been acclaimed as Nantucket’s leading steak and seafood restaurant. You can dine inside or alfresco on a terrace with spectacular harbor views. It’s the perfect place to watch the sunset while enjoying fresh lobster, poached halibut or a filet mignon.

Nantucket Island Resorts also owns and manages the nearby White Elephant Village where contemporary, island-inspired rooms and residences are just steps from town. These come with a concierge, pool with private cabanas, complimentary bicycles and more. Guests who want to be at the town’s hyperactive marina can stay at The Cottages at Nantucket Boat Basin, which include cottages and lofts, decks with harbor views, gourmet kitchens and pet-friendly options.

Another excellent in-town accommodation is the Jared Coffin House, the island’s first mansion and a centerpiece of the historic district. It was built in 1845 by Mr. Coffin, one of the most successful ship owners during the island’s whaling days. The hotel offers impeccable concierge service, atmospheric rooms with modern amenities and its own steakhouse, which serves lunch and dinner.

Be sure not to miss The Wauwinet, the island’s only Relais & Châteaux property. Situated on the northeastern side of the island, about 9 miles from town, it’s easy to get to this seaside refuge by road on the inn’s private jitney or by water on the Lady Wauwinet ferry. This grande dame of an inn first welcomed guests in 1875. After falling into disrepair over the years, it reopened in 1988 after extensive renovations.

The property particularly appeals to those seeking a tranquil, romantic getaway. Luxurious rooms feature custom furnishings and fine linens. An expansive lawn with chaise lounges overlooks the harbor.

Inside, antiques embellish a cozy living room that doubles as a book-filled library. Art from the owner’s collection graces hallway walls.

The Wauwinet’s Spa by the Sea offers a variety of treatments, from facials to massages, including a popular detoxifying body massage and algae wrap.

Another highlight here is award-winning Topper’s Restaurant, considered one of New England’s best places to dine. And for good reason. Dishes are artfully presented and every flavor stands out, whether it’s a delicate, multilayered appetizer of broccoli rabe and truffles or a main course such as poached lobster. Serving around 1,450 wines, the restaurant has repeatedly received the prestigious Wine Spectator Grand Award.

If you’re considering a Nantucket sojourn, the summer high season can certainly be fun. But don’t rule out the shoulder seasons when you can enjoy the island absent the crowds.
OTHER DINING OPTIONS

Black-Eyed Susan’s: For large homemade omelets, buttermilk pancakes and “scrambles” (the Portuguese scramble has linguica, tomatoes, spinach and garlic). Get there early since there’s always a line for breakfast.

The Nautilus: For craft cocktails, seafood small plates (charred Spanish octopus, yellowfin tuna lettuce wraps, crispy marinated calamari, and much more). In high season, you may have to reserve a table in early afternoon for dinner.

Cru: For a seafood raw bar and mains such as butter poached lobster and grilled Wester Ross salmon. Both the restaurant and two convivial bars overlook Nantucket’s waterfront.

The Chanticleer: For main courses such as New Zealand lamb, tenderloins and Maine diver scallops. Originally a teahouse, this romantic French restaurant in the town of Sconset is situated among beautiful gardens.

Cisco Brewers: For food truck snacks, beer, wine and spirits. This combination winery, brewery and distillery offers tours and live music.

SHOPS & GALLERIES

Sylvia Antiques: Established in 1927, this top source for antiques offers marine artifacts, folk art, lightship baskets, carvings, sculptures and other rare items.

Artists Association of Nantucket: The association’s Washington Street gallery showcases the work of local artists and offers educational programs for both children and adults.

Peter Beaton Hat Studio: Owner Darcy Creech sells custom- fitted hats and totes made from finely braided leghorn straw.

Murray’s Toggery Shop: You’ll find New England apparel and accessories for men and women, including the iconic Nantucket Reds, pants originally made of red canvas material meant to fade over time.

Nantucket Looms: This store sells quality apparel and accessories, luxury home décor and special occasion gifts.

Hostetler Gallery: Paintings and sculptures by the late artist David Hostetler and others grace the gallery’s spaces and walls.

Craftmasters of Nantucket: The shop offers quality home décor, accessories, belts and buckles, knives and scrimshaw with nautical themes.