Roll like a Rockefeller

High Society Holiday in New York State

New York

Duration: 15 nights

Price: From £3,550 per person in low season based on two adults travelling together and including all flights in economy class, accommodation on a bed and breakfast basis, private transfers, transportation, experiences as stated and taxes

Roll like a Rockefeller; style-it up like Jackie O, and revel in the playgrounds of the New York State elite on this “high society” holiday. Starting in New York, you’ll stay at Art Deco hotel, The Surrey, for jazz-age romance and speakeasy cocktail-making, before joining the bright young things in The Hamptons, relishing the great outdoors at the Rockefeller’s former hunting lodge, and enjoying the history, amazing cuisine, and thoroughly decadent lifestyle of upstate New York.
Perfect forStylish couples who love history, food, wine, and all things pertaining to the finer things in life.
In the knowConsider heading north and crossing the border into Canada. Here you’ll find the farmers markets, organic food, and vineyards continued, along with a whole wealth of history and spectacular scenery.

Best for

  • Couples
  • Food & Wine
  • Landscapes & Scenery
  • Off the Beaten Track

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Itinerary details

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Fly to New York, and enjoy a decadent three nights at Art Deco hotel, The Surrey, which stands in splendour on illustrious Fifth Avenue. Built in 1926, The Surrey was originally designed as a ‘residence hotel’ – and what a residence it was having played host to Bette Davis, JFK, and Claudette Colbert. Today it’s the epitome of New York sophistication, with a luxurious but low-key feel, and a private roof terrace with incredible views over the city. Staying here you’ll be perfectly placed for Breakfast at Tiffany’s, shopping on Fifth Avenue, and generally enjoying the pampered lifestyle of a well-heeled New Yorker, before taking an architectural tour of the city’s sky-line time-line, learning more about Penn Station in its glory days, and slinking into one of our favourite speakeasies to make some classic 1920s cocktails.
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There are times when even New York’s movers and shakers need some time away from the city, and that’s exactly what you’ll do for two nights in The Hamptons. From the bright young things of the 1920s, who rampaged around The Hamptons in the name of ‘conspicuous consumption,’ to the likes of Jackie O who retired here for a low-key summer escape, The Hamptons have been a playground for the rich and famous for centuries. In keeping with the historic spin of this escape, we’ve got you staying at the 1770 House Hotel, which sits in the heart of East Hampton, radiates white-picketed charm, and is the perfect spot from which to enjoy those long walks along the beach, amazing lobster, and sunset parties that keep the glitterati coming here year after year.
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After a few days partying with The Hamptons’ elite, you’ll slow the pace right down and be transported to the altogether gentler and more refined era of Glenmere Mansion (an hour‘s drive out of New York City). Built by Carrere and Hastings in 1911 (the same architects behind the New York Public Library), Glenmere Mansion is a beautiful Italian-inspired mansion, which having been restored extensively is now one of the finest country homes in America. If a silver-spoon existence is your idea of bliss, then you’ll be reluctant to set foot out of this Relais and Chateaux hotel, what with its gorgeous spa, exquisite gardens, and gourmet cuisine that makes you long to return to the Gilded Age. However, if you’d like to inject a little bit more history into your stay here, we highly recommend taking a walk through the Hudson Valley with a Native American Indian guide.
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Your high society escape will have been the height of indulgence thus far, so some time spent in the state’s North Country will give you the chance to blow away the cobwebs, and mingle with the country-set in the great outdoors. Hidden away on the edge of Saranac Lake, The Point was built by the Rockefellers in the grand tradition of Adirondack lodges, as a place for them to hunt, shoot, fish – and generally escape the stresses of Wall Street. Whether you’re here during “fall” or “summering” as high society once did, Relais and Chateaux The Point is now an ultra-exclusive bolt-hole surrounded by the timeless and stunning scenery around Saranac Lake. Head out for a day of riding, mountain biking, and canoeing in their beautiful mahogany vessels, before being welcomed back into what feels like a private family lodge, and enjoying the old-fashioned pleasures of great food and great company.
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By the final leg of your ultra-luxurious itinerary, one will have become so used to staying in elite enclaves, that the only place one could possibly contemplate staying in the Finger Lakes is the private island retreat of Geneva on the Lake. A 1914 Italianate villa, the hotel was built by a group of Philadelphia billionaires, and has both stunning views over Seneca Lake, and beautifully tended gardens which could almost rival the Italian Lakes. Whilst here, you’ll enjoy the most courteous and elegant service, amazing cuisine, and the Finger Lakes wine region which is easily on a par with Sonoma and Napa Valley. Stride out of Geneva on the Lake in Great Gatsby style, and glide through the next few days with croquet on the lawn, walks in Seneca Lake State Park, and water sports. We also recommend a visit to the Ivy League universities of Hobart and William Smith, before touring the wineries and farmers markets and dressing up in the evenings for the truly excellent dinners. Finally, after one last root-beer float (a Finger Lakes ice-cream served up since the 1930s), you’ll be driven back to Syracuse and take a domestic flight to New York City where you'll catch your return flight home.
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Best time to go

Best time to travel

Good time to travel (but some limitations)

Travel is possible (but it’s not the best time)

Travel is not recommended

  • Jan
  • Feb
  • Mar
  • Apr
  • May
  • Jun
  • Jul
  • Aug
  • Sep
  • Oct
  • Nov
  • Dec
Best time to go

Hotel locations for this itinerary

Hotels we've recommended for this trip


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