Before Nantucket became famous as a billionaire summer playground, the storied island 30 miles off Cape Cod, Massachusetts, has long captivated visitors with its quaint cobblestone streets, wild windswept beaches, and fascinating history as a global whaling capital.
The name Nantucket originates from the language of the indigenous Wampanoag people and translates to “faraway land.” That sense of getting away from it all still comes through despite the annual influx of tourists and uber-wealthy seasonal residents. The first colonial settlers arrived in 1659. Within a century, Nantucket became a major whaling port, inspiring Herman Melville to write the classic Moby Dick, which turns 175 this year. Whaling infused the island with wealth before the industry collapsed after petroleum was discovered in 1859. Catering to summer tourists eventually filled the economic gap. Today, strict local preservation laws maintain the island’s charming 19th-century character, while bans on chain businesses ensure that hotels, restaurants, and shops reflect its preppy coastal flavor and culture of quiet luxury.
A short walk from the bustling downtown area filled with boutiques, art galleries, and restaurants takes you down narrow streets lined with weathered gray cedar-shingled cottages and grand Federal-style captain’s houses adorned with overflowing flower boxes and ubiquitous hydrangeas.
Hop on a bike to explore the island’s natural wonders, including more than 80 miles of golden-sand beaches and untouched conservation land — nearly half the island is permanently protected from development. There are also three iconic lighthouses at Brant Point, Sankaty Head, and Great Point.
Where to Stay
The White Elephant, the island’s landmark resort, sprawls across Easton Street on the edge of Nantucket Harbor, a short walk from Main Street.
Entering the lobby, guests are greeted by a striking painting depicting a woman rowing a boat titled Elizabeth, an homage to the resort’s plucky founder Elizabeth T. Ludwig. Her vision of building a grand waterfront hotel in 1917 was mocked by her high-society friends as being a white elephant, referring to the old expression about a useless possession that is expensive to maintain. She defiantly named the hotel just that when it opened in 1920.
Colorful paintings depicting marine life and nautical themes hang throughout the hotel, which underwent a top-to-bottom renovation in 2023, bringing a whimsical, updated spin on New England coastal-cottage style with hues of ocean-blue and cream complementing the gray cedar exterior shingles
Accommodations range from rooms and suites in the main hotel, garden cottages, nearby White Elephant Village residences, and downtown lofts. Amenities include the Darya spa, a heated swimming pool, and the waterfront Brant Point Grill serving locally sourced seafood and steaks, plus a signature lobster bloody mary.
The Brant takes a chic boutique hotel approach to elevating the bed-and-breakfast concept, located around the corner from The White Elephant in the prime Brant Point neighborhood. Managed by SALT hotels, the enclave of four buildings around a central lawn with a plunge pool offers 26 guest rooms and suites. The laid-back beachy vibe is clean and contemporary with wood floors and beams, a neutral palette punctuated with orange throws, and stunning local photographs by Michael Gaillard throughout.
The property’s three original historic buildings built in 17th-century replica style are anchored by The Barn, the main social hub that doubles as a reception, cocktail bar, and lounge. In the mornings, the lobby bar transforms into a breakfast spot serving quiche, baked goods, and Greek yogurt with mix-ins. A chill soundtrack sets the tone.
A partnership with a local bike rental shop offers guests complimentary use of bicycles and discounted e-bikes for exploring the island’s miles of paved flat trails.
The Wauwinet is located nine miles from town on an isolated northeastern peninsula offering a serene and romantic adults-only setting. Founded in 1876 as one of the island’s first hotels after the whaling industry collapsed, The Wauwinet was named for a Wampanoag chief who once ruled the area. This year, the shingle-style retreat marks its 150th anniversary with engaging historical tours, tasting menus, and more.
The hideaway offers a choice of beaches between a rustic Atlantic shore with rolling sand dunes and the tranquil waters of Nantucket Bay. The Lady Wauwinet, an open-air motor launch, transports guests between The Wauwinet and its sister property, The White Elephant. Complimentary bikes are available for exploring the adjacent Coskata-Coatue Wildlife Refuge.
As the island’s only Relais & Châteaux, food and wine are paramount. Toppers ranks among New England’s highest-rated restaurants with hyper-local dock-to-table seafood, including its proprietary Retsyo oysters harvested a mere 300 yards away in the Bay.
Chef Kyle Zachary partners with local producers to bring a refined approach to coastal mainstays, such as a butter-poached Maine lobster roll served on a house-made brioche bun with lemon aioli. The impressive wine cellar holding more than 2,200 labels has received the prestigious Wine Spectator Grand Award since 1996.
Where to Eat and Drink
Galley Beach, a former clam shack on the sands of the north shore’s Cliffside Beach, has evolved into a new American coastal cuisine destination with an open-air dining room and beach dining, where you can take in spectacular sunsets with your toes in the sand.
The Proprietors Bar + Table is tucked away in a historic 1700s home on India Street, honoring the island’s whaling history with globally inspired, family-style small plates highlighting seasonal menus and creative craft cocktails.
Ethos Wine Bar & Bistro is a cozy neighborhood spot set in an 1840s building and run by a trio of veteran women sommeliers who curate a rotating list of global vintages, in addition to craft cocktails and a farm-to-table bistro menu complementing the wines.
Straight Wharf Fish is the casual sibling to the waterfront Straight Wharf Restaurant, delivering the same great harbor views with an upscale clam shack concept that includes a seafood market and eatery serving local oysters, crispy clam rolls and caviar onion rings.
Cisco Brewers, the local craft brewery, winery and distillery, has created a vibrant, family-friendly social scene in a rustic courtyard with live music, local food trucks, and an easy-going beach-town vibe. They also provide shuttle service to and from downtown.
What to Do
Hit the beach — the island’s many pristine natural shorelines offer a choice of gentle, calm waters on the north shore or heavier surf on the Atlantic side, including Madaket for spectacular summer sunsets.
Book a cruise on a classic wooden sailing yacht like The Blue Peter, a luxury motor yacht or a sport-fishing vessel.
Visit the Whaling Museum to immerse yourself in the island’s maritime history, featuring a restored 1847 candle factory and a 46-foot sperm whale skeleton.
Bike to Siasconset (pronounced Sconset) on the scenic Milestone Road path to this picturesque village with the Sconset Bluff Walk taking you past historic cedar-shingled cottages draped in climbing pink roses.
Shop independent galleries and boutiques, including the classic Murray’s Toggery Shop — home of the famous “Nantucket Reds” canvas trousers; Alice Walk, specializing in linen dresses and sumptuous cashmere sweaters; and Nomad featuring artful home accessories, including throws, pillows, and glassware. For gifts and mementoes, stop at Four Winds Gifts, a local institution since 1970, before boarding the ferry home.
Featured image courtesy of White Elephant Resorts. Travel Curator may earn a commission from booking links on this page
