Hydrangeas, Oysters and Lighthouses: How to Explore Nantucket Like a Local
From shingled cottages to the best lobster rolls, this is Nantucket at its finest.
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When it comes to New England resort towns, Nantucket is often considered the pinnacle—or, dare we say, the great white whale—of East Coast summer getaways. It’s a fitting reputation considering Nantucket initially rose to prominence as the whaling capital of the world (and its central role in Moby-Dick). As the whaling industry began to decline in the late 19th century, however, the island emerged as a popular vacation destination. Today, Nantucket is known as a preppy playground on the Atlantic Ocean—the coastal grandmother aesthetic thrived on the island long before it started trending on TikTok.
Nantucket is nearly impossible to get to, but its relative inaccessibility only serves to further emphasize its exclusivity. As of 1969, Newport is accessible by bridge (much to old money’s chagrin), Cape Cod by car (agonizing Route 6 traffic notwithstanding), and Martha’s Vineyard, its nearest competitor, is only seven miles off the Massachusetts coast. Nantucket, by contrast, is thirty nautical miles out to sea, or a roughly two-hour traditional ferry ride. While direct flights to the island have expanded in recent years, the ever-present fog that gives Nantucket its nickname, "The Grey Lady," often thwarts air travelers. (This hasn’t deterred the growing fleet of private aircraft at Nantucket Memorial.)
But, on Nantucket, you accept the chaos of the elements—the fog, the rain, the Atlantic winds—as part of the experience. When you land on the island, you truly feel you’ve arrived, entering a veritable paradise surrounded by miles of ocean and acres of golden beaches. Much of Nantucket’s beauty comes from its simplicity: purple hydrangeas lining gray shingled cottages, sand-strewn roads winding through sea-green beach grass. The uniformly charming architecture is by design—as a National Historic Landmark, every house is subject to architectural regulations. Hence, Nantucket-style cedar shingles and pitched roofs predominate, and the quaint, cobblestone streets draw the East Coast elite from Washington, D.C., to Boston for annual pilgrimages.
Many seasonal residents avoid the crowded summer season, opting for other peak (off-peak) times of year, including scalloping season, which is feted with a Scalloper’s Ball in early October, along with the Christmas Stroll in December, and Daffodil Festival in April. Yet, there’s still a wild magic to Nantucket that’s waiting to be discovered in the summer, its wind-swept beauty best appreciated far from the maddening crowds. (And it’s not the Hamptons, so try not to get wrapped up in the social climbing prevalent on the South Fork of Long Island.)
My journeys to Nantucket have evolved over the years, from high school sailing trips, to college reunion weekends, to share-house slumming, to the guest cottages of family friends. I’ve visited a dozen times, in all seasons and circumstances, and have compiled the best places to dine, stay and play on Nantucket. The island may be only 14 miles long and 3.5 miles wide, but there is more than enough to satiate the weekend explorer far longer than Thursday to Monday. After one visit, you’ll already want to come bACK.
The Ultimate Nantucket Travel Guide
Where to Stay
The White Elephant
- 50 Easton St, Nantucket, MA 02554
The White Elephant is a Nantucket institution. Its origins date back to the 1920s, when it existed as a collection of shingled cottages overlooking Nantucket Harbor. A century later, the property underwent a multimillion-dollar renovation, completed this past April—think coastal blue hues, grass cloth wall coverings and basket-weave carpeting, all inspired by the surrounding landscape. While the amenities have been upgraded over the years, the stunning waterfront view remains blessedly the same. Alongside 54 rooms and suites, the boutique hotel includes 11 cottages for guests to truly feel like a local—for the weekend, at least. And, as anyone who’s invested in Nantucket real estate knows, location is everything. The White Elephant is in the heart of downtown, perfect for exploring the cobblestone streets and shops without being stuck in the dreaded island traffic, which grows to a standstill come late July and August.
The Wauwinet
- 120 Wauwinet Rd, Nantucket, MA 02584
If you’re looking to escape the crowds, head to the remote northeastern shores for a stay at The Wauwinet. Though only nine miles from downtown Nantucket, the secluded property feels light years away from the bustling crowds disembarking from the ferry. The Relais & Châteaux retreat is next to the Coskata-Coatue Wildlife Refuge, 390 rugged acres of windswept coastline and barrier islands, and offers private beach access along both the Nantucket Bay and the Atlantic Ocean—forget schlepping your beach chairs and blankets across the bluffs to a crowded beach on the South Shore. One of Nantucket’s oldest hotels, the property was built in 1845 and features 32 rooms and four guest cottages. Children under the age of 12 are prohibited, so serenity is guaranteed. Book a dinner reservation at Topper’s, and catch the sunset from the Adirondack chairs on the sprawling front lawn.
The Nantucket Inn
- 1 Miller Ln, Nantucket, MA 02554
Head west to The Nantucket Inn, an oasis dedicated to the spirit of “Old Nantucket”—laid-back, unpretentious, coastal charm. The hotel’s ethos harkens back to a time before the island was swarmed with tony tourists and $50 lobster rolls. The 100-room Inn is the largest hotel on the island, though accommodations are tucked away amidst three acres of manicured gardens, cobblestone paths and shingled cottages with flower-strewn window boxes. The Inn is home to the island’s only hard tennis courts that don’t require a club membership, as well as the sole indoor pool—convenient for a year-round property. After all, to truly explore ACK like a local is to visit Nantucket in the off-season. September is considered the best month by seasonal residents who rent out their cottages from Memorial Day to Labor Day. The water is swimmable—the icy Atlantic doesn’t warm until August, anyway—and beach days are sunny and bright.
What to Do
Endeavor Sailing
- Straight Wharf, Slip #1015, Nantucket, MA 02554
Nantucket is famous for its seafaring history, so it’s only right that the first order of business would be to set out to sea. The Endeavor is Nantucket island’s oldest sailing charter, a 31-foot sailboat built by Captain Jim Genther in 1982. He’s been operating from Slip #1015 on Straight Wharf ever since, and 40 years of experience have only enhanced the Captain’s storytelling abilities as he regales guests with island lore on twice-daily sails on the Nantucket Sound. The cruise is BYOB, and would-be sailors are encouraged to help with the crew, though you can also simply relax and enjoy the views. Private charters are also available for romantic sails or larger (or smaller) groups—and you can bring your dog on board, too. Once back on dry land, visit the nearby Nantucket Whaling Museum for a greater sense of the island’s maritime history, and don’t forget to stop for an ice cream at the Juice Bar across the street.
Sconset Bluff Walk
- 27 Bank St, Siasconset, MA 02564
If you’re not lucky enough to own a rose-strewn cottage in Siasconset (Sconset to locals), the bluff walk is your second-best bet. Since Sconset’s historic fish houses were built centuries before the ferry, many were designed to face the sea, and the public footpath amongst the bluffs is the best way to appreciate the gorgeous architecture and surrounding ocean views. The Sconset fish houses were first constructed when the neighborhood was established as a fishing village in the late 1600s, and these one-story, shingled structures, with their gable roofs and small-paned windows, have since been preserved as charming, flower-adorned vacation homes. Peek at the houses’ names, displayed on quarterboards—nautical signage once required by maritime law in the early 1800s. When whaling declined, sailors repurposed the signs on their island homes, starting a tradition that continues to this day.
Bartlett’s Farm
- 33 Bartlett Farm Rd, Nantucket, MA 02554
ACK’s chicest grocery store is situated on the island’s oldest and largest farm: The sprawling, 200-acre Bartlett’s. Much of the cultivated land is certified organic, and the cheese selection is to-die-for. While getting groceries is usually the least exciting part of one’s day, at Bartlett’s, picking up your beach sandwich is a see-and-be-seen situation. Just try to arrive earlier in the day, as the wait time for a sandwich can grow up to an hour during the midday lunch. Afterward, take your farm-to-shopping-bag goodies to nearby Ladies Beach on the South Shore, or head north for wilder pastures and coastline.
Great Point
- Great Point Rd, Nantucket, MA 02554
Head north on the road less traveled to Great Point, the wild and pristine seven-mile-long barrier beach off the northeastern tip of Nantucket. Similar to beaches like Nobadeer, four-wheel drive vehicles are allowed on Great Point. But while “Brobadeer” is known for its party vibe, Great Point is stunningly remote, requiring a separate permit from town beaches (the over-sand vehicle permit can be purchased at The Wauwinet gatehouse). Drivers must also deflate their tires before heading onto the sand, but once on the point, it’s perfection—the journey is worth it for the views alone. The simplicity of the white sand, green beach grass, and deep blue North Atlantic sea is breathtaking, especially when observed against the iconic 60-foot Great Point Lighthouse. Cast a line, sunbathe and take a dip in the waves—just keep watch for seals. (They love this part of the island, so sharks are a major concern.)
Where to Eat
Black-Eyed Susan's
- 10 India St, Nantucket, MA 02554
Start your day with the best breakfast in town, served daily for 30 years. Located right in downtown, this unpretentious, laid-back indoor/outdoor establishment on India Street serves up morning classics like eggs Benedict and huevos rancheros alongside clever twists on breakfast favorites like sourdough French toast with Jack Daniels butter. The morning shift is walk-in only, so head there early if you want a prime seat. If you can’t get enough, the tavern is great for dinner, too (and accepts reservations in the evening). The reasonable pricing and BYOB policy make this a more affordable option for an evening out. And if you miss out on the morning seating and catch yourself trapped in a 10 a.m. line, head a mile south to mid-island to Island Kitchen, which boasts indoor/outdoor seating as well as a grab-and-go selection of seasonal items grown on-island.
167 Raw
- 167 Hummock Pond Rd, Nantucket, MA 02554
For a beachy lunch, head to 167 Raw along the island's South Shore. The fresh seafood market and food truck on Hummock Pond Road is home to some of the best fish tacos on the island. Grab some grub and head to nearby Cisco Beach, which is popular with surfers and sunbathers in the summertime. Another nearby beach option is Madaket, which allows small cooking fires in the evening—perfect for s'mores with friends. For an additional casual, beach-ready lunch alternative, head east to Sconset to pick up sandwiches at Claudette’s. The sandwich shop is located right near the entrance to Sconset Beach, which offers a more tranquil atmosphere for beachgoers on the easternmost tip of the island.
The Chanticleer
- 9 New St, Siasconset, MA 02564
If you choose to spend your beach day along the southeastern shore, plan to stay until the evening for dinner at another beloved Sconset restaurant: The Chanticleer. On an island renowned for its beauty and charm, Sconset stands out as perhaps the most quaint and picturesque neighborhood. So, it’s only fitting that the most romantic restaurant in town would be situated within one of its rose-covered cottages. The Chanticleer originated as a tea house in the early 1900s and has since become a hallmark of Nantucket elegance and fine dining. The Nantucket Wine & Food Festival grows in prestige and popularity every year as the island becomes more established as a high-end culinary destination.
Straight Wharf
- 6 Harbor Square, Nantucket, MA 02554
Head downtown for dinner overlooking the harbor at Straight Wharf, which is open for its 50th season this summer. The menu changes nightly based on the freshness of ingredients and seasonality of dishes, emphasizing natively-sourced ingredients. The clambake and scallops are always solid options for seafood lovers, and an extensive wine menu is sure to delight aspiring sommeliers. For a more casual option, the restaurant opened Straight Wharf Fish last summer as a clam market and fish market just next door on the harbor. The restaurant’s location is ideal for visitors looking to maximize their evenings on-island, as it is right in the center of the downtown bar scene.
Where to Shop
Murray's Toggery
- 62 Main St, Nantucket, MA 02554
When on Nantucket, dress as the natives do. The stereotype of islanders donning the salmon hues of Nantucket Reds is steeped in history, and true to this day. Murray’s Toggery is the homeland, with an entire section dedicated to Nantucket’s famous color. The shop’s legacy on the island traces back to 1843, when it was a dry goods store. It opened as the Toggery Shop in 1916 and was renamed after its new owner, Philip Murray, in 1945. Eighty years later, it remains an island institution. For true credibility, your Reds should be as worn-in as the color is designed to fade over time. Still, even if you’re a first-time visitor, it’s never too early for that process to start. For a more modern option, check out the unique, handcrafted apparel at Res Ipsa on India Street, which also has branches in Paris, Marrakech and Malibu.
Anna P. Jay
- 5 Washington St C, Nantucket, MA 02554
Accentuate your new island wardrobe with baubles from Anna P. Jay, a locally owned fine jewelry boutique downtown. Her Nantucket storefront, the Jewel Box, rotates a curated selection of female jewelry designers. For an equally island-appropriate accent to complement your Nantucket Reds, consider a Parker River Proper woven cuff bracelet with ivory scrimshaw depicting Sankaty Head Lighthouse or Brant Point Lighthouse. The tradition of Nantucket basket weaving dates back to the early 19th century, and is still the accessory of choice at island cocktail parties today. Head over to The Basket Shop for a bespoke experience customizing a piece of Nantucket history. Above all, take time to stroll through downtown, where you will find variation from traditional Nantucket architecture in the sea captains’ houses around Main Street—grand brick buildings built after the Great Fire of 1846.
Mitchell's Book Corner
- 54 Main St, Nantucket, MA 02554
Brush up on your Nantucket literature at Mitchell’s Book Corner on Main Street. Established in 1968, Mitchell’s has an extensive Nantucket section, which focuses on the island’s whaling history and contains extensive fiction and nonfiction books about New England. (A great chance to brush up on Moby-Dick if it’s been decades since you explored summer reading lists.) Check out the selection of Elin Hilderbrand paperbacks upstairs—the author is a Nantucket resident, and often hailed as the queen of the beach read. Her novels are addictive, transporting readers to the country roads and salty beaches of the island without booking a ferry—ideal for when you’ve headed home and long to return. (Plus, there’s a likelihood the copy will be signed by the author herself). Saunter up Centre Street to sister store Nantucket Bookworks, which has more eclectic lifestyle offerings, including gifts and a chocolate corner, with sweets from around the world.
Where to Drink
Cisco Brewers
- 5 Bartlett Farm Rd, Nantucket, MA 02554
Nantucket’s only craft brewery also happens to be the see-and-be-seen destination for the post-beach crowd. After your picnic lunch at Ladies Beach, head to nearby Cisco’s to enjoy some live music and local flavor, from the guests to the spirits. The brewery also features a vineyard and distillery, and the Triple Eight vodka is particularly popular—order a Triple Eight Lemonade, a refreshing blend of blueberry vodka, lemonade and club soda. Food trucks serving oysters, tacos and the like make this a one-stop destination for all your post-beach cravings. The earlier you arrive for your après-surf session, the better, as the line grows steadily throughout the afternoon, particularly on a summer weekend.
Sandbar
- 4 Bathing Beach Rd #2234, Nantucket, MA 02554
If you’d rather skip the long wait at Cisco, head over to Sandbar at Jetties Beach for afternoon drinks. The frozen cocktails are a favorite, as is the buck-a-shuck oyster hour, which serves $1 oysters from 3 to 5 p.m. The indoor/outdoor venue features a bar and high-top seating, wooden picnic benches, and Adirondack chairs clustered on the sand. The vibe is more laid-back than Cisco's, and boasts a beautiful sunset in the early evenings—sit back with a glass of rosé and take it all in. Expect live music Tuesday through Sunday in the summertime, with the popular local band Foggy Roots playing their signature island reggae on Saturday afternoons. Live music is a constant throughout Nantucket nightlife, and travelers should check the schedule for the Muse Summer Series to see which bands are performing during their stay.
The Club Car
- 1 Main St, Nantucket, MA 02554
Venture into the small town to visit The Club Car, a piano bar housed in a 19th-century train car on Main Street. The Club Car Cafe serves coastal-inspired fare in the building’s retrofitted railway interior, and live music begins every night from Thursday through Sunday at 9 p.m. The bar becomes quite popular on weekend nights, but there is an outdoor space for revelers looking for some air after belting out some classic favorites (think: Elton John, Billy Joel and the like). If you’re looking for a fun way to connect with the locals, this is it. Other alternatives downtown include the back patio at Ventuno’s and Cru, though the latter has more of a New York vibe than traditional New England. The Gazebo is another favored outdoor hangout overlooking the harbor, but you can expect it to be swarmed with college kids on a summer Saturday.
The Chicken Box
- 16 Dave St, Nantucket, MA 02554
Speaking of college, The Chicken Box is the late-night staple for a summer night, whether you’re 21 or decades older. Though the crowd does tend to skew younger, this is a Nantucket institution, and islanders return annually to catch a show or play pool, decades post-undergrad. Unlike other establishments on-island, ‘the Box,’ as it’s known to locals, maintains a distinctly unpretentious, dive bar-like atmosphere, with local draft beer and an outdoor patio for decompressing post-dancing. Live music spans an array of genres from blues to ‘90s pop to reggaeton. Arrive early—or before last call—to avoid a long line at the entrance, and download the bar’s app to pay your cover in advance. Relive your youth on the dance floor and grab a slice of Sophie T’s Pizza, located right across the street, on your way home.
