City, Countryside, Coast

New York City to Montauk

New York City, Country and Coast

Self-drive Tour

New York City – Catskills – Hudson Valley – Montauk

Explore this classic New York Trifecta in luxury, from the cityscapes and excitement of Manhattan, the rolling vineyards and historic estates of the Hudson Valley and the forested peaks of the Catskills. Continue to the elegant seaside villages and windswept beaches of Long Island with Atlantic views for a relaxing finale, as you blend city life, scenic countryside and laid-back coastal charm.

 

INCLUDES FLIGHTS
9 Days
From £3889 Per Person

Includes international flights from most UK airports on 5 October 2026. Subject to availability at the time of booking. Please call for details.

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New York City, Country and Coast
From £3889 Per Person

Your Itinerary

  • Day 1
  • Day 2-3
  • Day 4
  • Day 5
  • Day 6
  • Day 7
  • Day 8
  • Day 9

Day 1 : UK - New York City

Arrive in New York today and take a private transfer to your Manhattan hotel and check in for a 3-night stay. The rest of the day is at leisure for you to settle in and discover the city.

Hotel: Walker Hotel Greenwich Village

Day 2-3 : New York City

The next two days are free for you to experience New York. Walk Central Park, see skyline views from the Top of the Rock of Summit One Vanderbilt, and explore neighbourhoods from SoHo, Greenwich Village and artsy Williamsburg. Consider taking in a Broadway show or a sunset cruise.

Day 4 : Catskills - Hudson Valley

Head to Moynihan Train Hall at Penn Station this morning to take the Amtrak service to Poughkeepsie. Secure a window seat on the left side so that you may enjoy the Hudson River passing leafy suburbs and riverfront towns before crossing through rolling farmland. Upon arrival in Poughkeepsie, take a taxi locally to pick up your car hire before driving to your hotel. Check in for a 2-night stay at Inness in Accord, NY – a luxury country resort retreat.

Hotel: Inness

Day 5 : Catskills – Hudson Valley

Situated between the Catskills and Shawangunk Mountain ranges, this is the perfect place to explore upstate and is where artists, writers and naturalists have long drawn inspiration from tranquil forests and mountain getaways. There’s no shortage of cultural treasures, magnificent scenery and historic mansions with highlights including the FDR Presidential Library, Vanderbilt Mansion and the Walkway Over the Hudson in the Poughkeepsie area for breathtaking views. Then experience the Mohonk Preserve, take photos of iconic bridges and drive the Shawagunk Mountains Scenic Byway.

Day 6 : Montauk – Long Island

Begin the journey back through the countryside passing the city as you head to Long Island for a coastal escape. Arrive in Montauk this afternoon for a 3-night stay passing famous white sand beaches and Atlantic views along the way.

Hotel: Montauk Yacht Club

Day 7 : Long Island

Take in stunning ocean views from the top of the Montauk Lighthouse or tour the halls and gardens of the magnificent Gold Coast Mansions. The quirky hamlet of Montauk is known for fishing, beaches and parks, and is also just a short drive from the upscale communities of the Hamptons. Make sure to make a stop for some incredible seafood today.

Day 8 : Long Island

You may wish to drive further afield today and explore some of Long Island’s wineries – Wolffer Estate is just a short distance from Montauk. Alternatively, experience Montauk’s stunning sunrise then spend the day wandering its docks and streets and indulge in some local seafood.

Day 9 : Departure

Drive back to the airport to return your car today, ahead of your departing flight. The drive back to the airport will take you past Old Westbury and Oheka Castle, famous for its inspiration for the novel The Great Gatsby, and make sure to leave some time for shopping at Belmont Park Village too.

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We are very proud that our personal, friendly service and attention to detail has led to us becoming an industry leader in providing tailor-made holidays. We have been recognised throughout the years by winning a number of prestigious awards from within and outside of the travel industry. We won the "Best Operator to Canada" award at the 2017 British Annual Canada Travel Awards for a record 15th time.

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