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August 14, 2019updated Dec 20, 2023

A Voyage with Gurney’s Resorts

By Kristen Shirley

One of a Northeasterner’s most difficult summer dilemmas is choosing between the pristine shores of New England and the glamorous scene in the Hamptons. In a newly launched package, Gurney’s Resorts offers a trip that gives you the best of both worlds.

Begin your journey in one of the Hamptons’ newest hotels, Gurney’s Star Island in Montauk, New York, then board a private 65-ft yacht for a day trip to its classic hotel in Newport, Rhode Island

 Zip over to Montauk (we recommend traveling from New York City by Blade’s seaplane or helicopter to avoid the traffic), and check into Gurney’s Star Island. While the original Gurney’s Montauk (OG Gurney’s, to those in the know) has dramatic ocean views, the charming feel of Star Island feels like more of a relaxing escape.

There’s a regular shuttle between the two properties, so you can still dine at Scarpetta Beach and experience one of the Hamptons’ most fun beach parties. But back at Star Island, you won’t be bothered by daytime DJs, and the water in the marina is calm and still, making it perfect for little ones and for enjoying water sports.

After you’ve had your fill of the Hamptons, it’s time to hop aboard the chicest way to get to Newport: a 65-ft yacht named Shameless. She’s fully equipped for the two-hour voyage, and Gurney’s can provide whatever catering and bar set up you desire, including the classic lobster roll and rosé pairing. Watch Montauk’s lighthouse slip from view and enjoy the open ocean while you soak up the sun during the breezy trip.

As you approach Newport, you’ll know it: The water is suddenly full of sailboats, whether there’s a regatta happening or not. Have a perfect seaside lunch at The Pineapple Club, Gurney’s Newport’s charming seaside restaurant. Be sure to order the Seafood Tower and the famous BBQ Hot Dog (really) to get into the local spirit. You can spend the afternoon relaxing on property, or head out into town and see the famous Newport Mansions. There are plenty of tours available, but if you just want to get a feel for them, rent a three-wheeled scooter and explore the town on your own. Return back to Montauk before dark so you can enjoy the incredible sunset from the water.

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End your trip at Showfish, Gurney’s Star Island’s sensational seafood restaurant where you can tuck into a feast of the freshest fish with the gentle sound of waves behind you. The crudos are not to be missed, nor is the grilled Spanish octopus or the seared scallops. But the star of the menu is certainly the house-dry-aged bone-in ‘tuna ribeye,’ which has incredible flavor and an Instagram-worthy presentation. 

The roundtrip charter from Montauk to Newport is $4,800 plus tip. If you get seasick, take to the skies with a roundtrip helicopter charter for up to three people $1,700. Visit for more information.

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