The Wauwinet, Nantucket

With cobblestone streets, silver-cedar storybook cottages flying Old Glory and unspoiled beaches tucked away on a boomerang-shaped island 30 miles off the coast of Massachusetts, Nantucket is the quintessential American summer destination. And the getaway from the getaway is The Wauwinet. Sandwiched between the bay and the ocean on the island’s remote east end, the inn boasts two beaches, acres of chaise-filled lawns and outdoor pursuits, all in a laid-back lap of luxury.
Dating from 1875, but renovated and redesigned in 2019, The Wauwinet is a best-of-both-era’s romantic retreat with its adults-only ambience and gourmet food and wine program. The fine dining venue Topper’s delivers beautiful bay views and the largest wine list on the island with some 2,500 bottles. The restaurant’s focus on fresh-caught seafood takes the “locally sourced” ethic to extremes, tapping oyster beds just 300 yards away.
The inn’s four standalone cottages and 32 guest rooms (starting at $1,050 in the summer) have all the modern amenities in a blend of preppy sophistication. But you’ll likely be tempted outdoors to walk the countryside, lounge on one of the private beaches, enjoy watersports, play tennis or grab a complimentary bike to explore the island. A partnership with BMW lets you book a loaner vehicle and regular shuttles go to town. The concierge will fix you up with a tee time at the Miacomet or Siasconset golf course or put you on a lobstering expedition on the Wauwinet Lady.
While The Wauwinet is smoke-free in public spaces, it’s otherwise still quite smoker friendly. Aficionados like to take their cigars for a walk on the beach, enjoy them on the Zen Deck or light up while gazing to the sea at the end of the property’s long dock.