New England is dotted with charming seaside towns, but Nantucket has a magic that feels all its own. Just 30 miles off the coast of Cape Cod, this small island—once a bustling whaling hub—has transformed into one of Massachusetts’s most irresistible summer destinations. Think cobblestone streets, gray-shingled cottages draped in Nantucket blue hydrangeas, windswept beaches, and a food-and-drink scene that rivals any big city. No wonder the National Park Service named the entire historic district a landmark back in 1966: here, every corner seems to whisper its maritime past.
Recently, I hopped on a quick flight from New York City and discovered firsthand why Nantucket has earned its reputation as a New England gem. From cozy breakfasts to sunset cruises, here’s how to make the most of your stay.
Where to Stay
In the heart of downtown, Faraway Hotel makes for the perfect base. Spread across six thoughtfully restored buildings and anchored by a leafy courtyard restaurant, the property combines easygoing island spirit with modern design. Best of all, it’s within walking distance of both the beach and the town’s best shopping.
Where to Eat & Drink
- Breakfast staples: Start the day with a stop at Lemon Press on Main Street. Its coffee and avocado toast are practically legendary. For heartier, old-school plates—eggs, pancakes, and more—Black Eyed Susan’s is the beloved local institution.
- Lunch by the water: For the island’s most talked-about lobster roll, head straight to Cru. Overlooking the harbor, it’s the kind of place where lunch easily slides into cocktails as the sun sets.
- Dinner with a view: If you’re in the mood to dress up, Topper’s at the Wauwinet serves elegant dishes with sweeping views of Nantucket Bay. The Chanticleer is another standout, with garden-grown ingredients adding freshness to every plate.
- Sweet indulgence: Nothing says summer like a scoop from The Juice Bar. Expect long lines and creamy, homemade flavors that are worth the wait.
- Nightlife: For a laid-back afternoon that turns into evening, Cisco Brewers offers craft beers, food trucks, and live music. Cocktail lovers should make for The Nautilus, known for its inventive menu, while The Club Car guarantees nightly live performances in a vintage train car setting.
Shopping the Island
No trip to Nantucket is complete without a stop at Murray’s Toggery Shop, home of the original Nantucket Reds. Want to pack the island look before you even arrive? Tuckernuck has a rotating collection of New England–inspired styles online. Downtown, browse Veronica Beard for polished classics, or Vineyard Vines for playful, coastal staples. For something more nostalgic, Four Winds—the island’s oldest gift shop—stocks charming keepsakes. I couldn’t resist leaving with a pair of woven basket earrings destined to be my summer favorite.
Exploring Beyond Downtown
Though Nantucket’s historic core is walkable, a bike opens up the rest of the island. Pedal east to Siasconset Village and wander the Bluff Walk, a flower-framed path that leads to Sankaty Head Lighthouse.
Beach lovers are spoiled for choice: Surfside, Jetties, Ladies Beach, and Children’s Beach all deliver soft sand and rolling Atlantic waves. For nature lovers, the trails at Tupancy Links offer quiet coastal beauty, while thrill-seekers can try off-roading out to Great Point.
And don’t skip the water. Whether it’s a fishing excursion, a leisurely harbor tour, or a romantic sail, there’s no better way to appreciate the island than by boat. One standout? The sunset cruise from the White Elephant Hotel to Topper’s—pure Nantucket magic.
The Takeaway
Nantucket is more than just a pretty island—it’s a blend of history, style, and effortless coastal living. Whether you’re savoring lobster rolls by the harbor, cycling to a windswept lighthouse, or dancing to live music at Cisco, you’ll leave with the sense that you’ve stepped into a postcard. And like all the best escapes, you’ll already be planning your return before the ferry pulls away.
