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Island Time: Nantucket

Even if you’ve been visiting this little slice of paradise for years, here are a few gems you may not know about



A breathtaking place where island time is the only time—sun drenched beach days, warm ocean breezes and laid-back sophistication. This is Nantucket. Get to this New Englander’s paradise quickly and easily (no traffic jams and no ferry crowds) on Fly The Whale. The new airline is offering direct service from Westchester Airport in an eight passenger Cessna Grand Caravan Turbo Prop. For $575, you’re toes will be in the sand in under an hour. What’s even better is that it becomes $175 cheaper if you treat yourself to dinner at the Summer House Restaurant and Piano Bar. (Along with your bill you get $175 gift card to Fly the Whale.)

The Summer House, in the Sconset region of the island, is gorgeously set up on a bluff but guests can (and should) meander down to the beachside heated pool (a rarity in Nantucket) and al fresco bistro. The onsite cottages covered in roses are casual and family welcoming. One, two and three bedrooms ranging from $275—$2000/night are available. Many provide the comforts of home such as king beds, air conditioning, fireplaces, tumbled marble baths and full kitchens. 

Should you want to pop into town, no problem. The hotel runs a continuous shuttle to its new in-town sister properties, India Street Inn, The Pineapple Inn, The Summer House at 27 Fair and also 29 Fair Restaurant, known not only for its world class food but candlelit ambience.

Once in town, there’s a ton to do—wander the cobblestones streets and explore the charming historic buildings that neighbor the Madison Avenue-worthy boutiques. Scooters and bikes can be rented steps away from the ferry dock for wider-ranging excursions. 

If you are lucky enough—or smart enough—to plan your visit in mid-May, you will get to experience Nantucket Wine Festival. This five day-long event does not disappoint. Some highlights include:

  • The Opening Reception, Harbor Gala, La Fête and Grand Tastings are the festival’s staple events. 
  • Complimentary to the signature events are wine and food seminars that provide education from those in the know.
  • The Great Wines in Grand Houses is a series of dinners hosted by islanders with jaw-dropping homes.
  • The culinary tent houses all-star chefs who put on demonstrations throughout the festival.
  • Special events such as, the Wheels Up VIP Hangar Party. When you have to leave they could arrange a ride home (or anywhere else in the world you may need to go).  

Restaurants also hold private events. We opted for the wine dinner at the Summer House Restaurant. The cocktail hour was filled with live piano music, passed hors d’oeuvres and glasses overflowing with the deliciously crisp Chateau d’Esclans Whispering Angel Rose. The sit-down, three course dinner featured wine pairings of Emmolo Sauvignon Blanc, Belle Glos Pinot Noir and Caymus Cabernet

No trip to Nantucket is complete without a last stop to the famous Galley Beach. Here, time literally stops when you curl up on one of the comfy couches right on the beach, watch the sun set from one of the best spots on the island and toast a weekend well spent.

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