The quaint island offers a wealth of fitness, food, and cultural activities.
May is a time for celebration in coastal New England, as the Massachusetts seashore comes alive again after a long winter. That’s especially so in Nantucket, an island located 30 miles south of Cape Cod. The historic town boasts late 18th-century seaport architecture and miles of sandy beaches, the majority of which are open to the public. But, there’s much more in store for active visitors on the island known as the Little Grey Lady of the Sea.
Getting there
There are no bridges connecting Nantucket to the the mainland, so it’s only accessible by air or sea. There are flights from many major airports and ferries from Cape Cod.
Where to stay
Check in at the White Elephant Hotel, a waterfront staple since the 1920s. The 67 guest rooms, suites, and garden cottages feature harbor views and cozy fireplaces. Sample the local classic, lobster, at the hotel’s Brant Point Grill.
Alternatively, The Wauwinet is a luxury inn on the northeastern shore bordering the Coskata-Coatue Wildlife Refuge. There are 32 rooms and four cottages to choose from and bikes available for getting around the island. TOPPER’S restaurant serves fresh green juices for breakfast, a raw seafood platter for lunch, and lobster-crab cakes in the evening.
What to do:
For the sea adventurer:
Nantucket is home to the annual Figawi sailing regatta every Memorial Day weekend. Get inspired and take a lesson at the Jetties Sailing Center, where you can also rent catamarans, kayaks, paddleboards, and windsurf boards. Those who’d rather leave the tiller in the hands of an expert can book a sunset sail out of Straight Wharf on the Endeavor with Captain Jim Genthner.
For the land explorer:
Despite its small size, the island has 33 miles of bike paths, most of which are safely separated from the roadways. Rent a bike at Young’s Bicycle Shop and cycle seven miles to Siasconset Beach, which is on the eastern tip of the island and home to the historic Sankaty Head Lighthouse. After doing the scenic Bluff Walk, hop back on your bike and follow trails to the western beaches such as Madaket and Dionis. Nantucket Bike Tours also offers a 20-mile guided tour that includes the Moors of Nantucket, Cranberry Bogs, and Sconset Bluff.
For the history buff:
To learn about the locale’s seafaring heritage, visit the Shipwreck & Lifesaving Museum. The site houses permanent and changing exhibits telling the stories of famous shipwrecks and rescues over the centuries. Less than five miles east down Polpis Road is the First Congregational Church, where you can climb up the 94 tower steps and take in the best view of the island. The church’s vestry dates back to 1725.
Where to eat
For breakfast:
Start the day at The Green, with a vegan breakfast sandwich with almond butter, avocado, and kale or a beet smoothie with blueberries, raspberries, ginger, and apple.
For lunch:
The Straight Wharf restaurant on Harbor Square has been feeding visitors to Nantucket for 44 years. Order the smoked bluefish paté on Melba toast, the chilled peach and fennel soup, and finish with the swordfish tacos and scarlet runner bean salad. After lunch, sample local wines at the Nantucket Vineyard Winery or, if beer is more to your taste, nearby favorite Cisco Brewers offers tastings and tours.
For dinner:
Book in advance at The Nautilus Nantucket, where New England seafood blends with elements of Southeast Asian street food, traditional Japanese izakaya, and Spanish tapas. Start with the lobster tostada and yellowfin tuna lettuce wraps, then share the shellfish curry.
The restaurant at Ships Inn has a more traditional Nantucket dinner menu, offering appetizers like oysters, broiled clams, and seafood chowder, and entrées including cod medallions, Dover sole, and wild king salmon.
For a nightcap:
End the evening at Ventuno’s Back Bar. Mingle with locals on the vine-covered patio over a cocktail or a bottle of bubbles.