Hydrangeas, Oysters and Lighthouses: How to Explore Nantucket Like a Local

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.