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  • 3 Day Itinerary: The Hamptons, New York

    Day 1

    Morning: Hop on the Hampton Jitney from various spots in New York City

    Base yourself in Riverhead if you want to be between the forks or in Southampton if you want that quintessential Hamptons style experience, both are accessible on the Jitney. Car rental when you reach the area is a great option as the roads are not busy.

    Evening: Welcome to the Hamptons – Southampton Village

    Stroll around Southampton Village, a historic gem or book a tour to guide you. The town has a charming and Hampton-esque downtown that will draw you in with a variety of boutiques, great restaurants and cultural venues. Grab a healthy organic lunch and a freshly brewed coffee at ‘The Golden Pear’ or ‘The Village Gourmet Cheese Shoppe’. If you are here in summer jump on a bike and head down to Coopers Beach, ranked as one of the country’s best beaches. Head back to Southampton for dinner – and keep an eye out for any celebs.

    Oheka Castle, Long Island, New York | TravelManagers

    Day 2

    Explore the North Folk wineries and try the oysters

    The North Fork “NOFO” is a down-to-earth alternative to the star-studded scene in the Hamptons. “NOFO” is home to more than 60 wineries and miles of farmland, and is one of the country’s most exciting wine and culinary regions. Enjoy the whole day in the North Fork with your car or even better on a guided wine and farm tour. The team at Classic Wine Country Tours do an excellent five hour guided farm and vineyard bike tour. Visitors will be amazed by the quality of the “foodie” experiences, from oyster farms to olive oil tasting, so close to New York City. Customers can book this via Viator “Mattituck New York Guided Farm and Wine Country Bike Tour If you are exploring on your own, dinner at Noah’s, a New American restaurant with locally sourced ingredients, is a must if you still have room!

    Day 3

    Take a tour of the great mansions

    When driving back towards NYC, step inside Long Island’s Gold Coast for a look into the elegant and opulent lifestyles of the elite. Owned by past presidents, artists and aristocracy, many of these homes once hosted royalty, heads of state and stars such as Charlie Chaplin. These mansions are often the backdrop for Hollywood productions, the Gold Coast mansions also served as inspiration for The Great Gatsby. Open for tours and events, travel back to a bygone era when you visit these estates. Visitors can spend the night in OHEKA castle and walk in the footsteps of the rich and famous.

    Montauk Lighthouse, Long Island, New York | TravelManagers

    How to get here?

    Did you know it’s only two hours from downtown New York to the heart of the Hamptons? The Hampton Jitney is a bus service that transports visitors and locals from various locations in downtown NYC to drop off points on Long Island including Riverhead, Southampton (in the Hamptons) and Sag Harbour. You can order tickets online. Trains also run from NYC up to Greenport in the North Fork and Southampton and Montauk in the South Fork, with stops along the way. Feeling flash? You can also book helicopters from NYC to the Hamptons.

    Where should I stay?

    • Capri Hotel Southampton
    • Topping Rose House
    • Gurney’s Montauk Resort & Seawater Spa Hamptons

    Special Hotel Offer

    Gurney's Montauk Resort & Seawater Spa Hamptons

    Montauck, New York

    2 nights from $592*pp per night twin share.

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