Combine the excitement of New York City with a completely different side of New York State on this 10-night rail holiday connecting Manhattan with the vineyards, coastal communities and relaxed character of Long Island’s East End.
Begin with three nights in New York City, giving you time to experience its famous landmarks, neighbourhoods, museums, restaurants and entertainment. From Central Park and Fifth Avenue to Lower Manhattan, Brooklyn Bridge and Broadway, discover the sights and experiences that make this one of the world’s great cities.
Then leave Manhattan behind and travel east by Long Island Rail Road to Riverhead for a seven-night stay. With no need to hire a car, settle into your base and discover the contrasting landscapes and communities of eastern Long Island.
Spend your days experiencing Riverhead and the North Fork, where vineyards, farms, local food and maritime communities reveal a quieter side of the state. Visit places such as Mattituck and Greenport, enjoy time beside the water or arrange excursions to discover more of Long Island’s beaches, Atlantic coastline and the Hamptons.
With seven nights on Long Island, there is time to balance days out with time to relax rather than moving from hotel to hotel. At the end of your stay, simply board the train for your journey back towards New York City and your onward travel arrangements.
From Manhattan skyscrapers to vineyards, beaches and waterfront communities, New York City & Long Island by Railbrings together two remarkably different experiences in one easy-to-navigate holiday, without the need to hire a car.
Love the itinerary but prefer the freedom of having your own vehicle? This holiday can also be adapted into a self-drive journey, with a rental car collected as you leave New York City and used throughout your stay on Long Island.
Travelling by car gives you even greater flexibility to discover the North Fork, Hamptons, Atlantic beaches, vineyards, farms and smaller coastal communities, creating each day around the places and experiences that interest you most.
Whether you prefer to travel by rail or road, a Discover North America Travel Specialist can tailor the itinerary around the way you want to experience New York City and Long Island.
All of our itineraries are fully customisable and can be tailored to suit your individual preferences. Whether you’d like to start or end in a different city, upgrade your hotel accommodation, or add sightseeing excursions to enrich your experience, your Discover North America Travel Specialist is here to help.
We don’t include international flights in our headline prices as standard, as we work with a wide range of scheduled airline partners and offer flexible options to suit your preferences. Factors such as departure airport, airline, travel class, travel dates, and seasonal promotions can all impact the final fare. Your Discover North America Travel Specialist will take the time to understand your individual requirements and source the best-value flights tailored to your itinerary.
Find out more about the process we follow here.
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Arrive in New York City on Day 1 and make your way to your hotel for a three-night stay. Spend your first afternoon and evening getting acquainted with Manhattan, perhaps walking through Times Square, enjoying dinner in one of the city’s neighbourhoods or taking in your first views of the famous skyline.
Over the next two days, discover some of New York City’s most iconic sights. Walk through Central Park, explore Fifth Avenue and Rockefeller Center, visit Grand Central Terminal or head downtown to the 9/11 Memorial, Wall Street and Lower Manhattan. Take to New York Harbor for views of the Statue of Liberty, cross Brooklyn Bridge or see the city from above at the Empire State Building, Top of the Rock or SUMMIT One Vanderbilt.
Make time to experience the city’s neighbourhoods too. Wander through Greenwich Village, SoHo and Chelsea, walk the High Line, visit one of New York’s world-famous museums or spend an evening enjoying a Broadway performance.
After three nights in Manhattan, your journey takes a completely different direction. On Day 4, make your way to the station and board the Long Island Rail Road for your journey east to Riverhead, where seven nights provide the opportunity to discover another side of New York State without the need to hire a car.
Leave the energy of Manhattan behind today as you make your way east by Long Island Rail Road to Riverhead, your base for the next seven nights on Long Island.
As the journey takes you away from New York City, the urban landscape gradually gives way to the communities and more open landscapes of Long Island. Depending on the service, a change of train may be required along the way before arriving in Riverhead.
After checking into your hotel, spend the remainder of the day getting acquainted with your new surroundings. Take a walk through downtown Riverhead, discover the waterfront along the Peconic River or enjoy a relaxed evening at one of the town’s restaurants.
With seven nights ahead, Riverhead provides a convenient base for experiencing a very different side of New York State, from the vineyards, farms and maritime communities of the North Fork to the beaches and coastal character of Long Island’s East End.
With six full days ahead, settle into the relaxed rhythm of Long Island’s East End and use Riverhead as your base for discovering a very different side of New York State.
Spend time getting to know Riverhead, from its Peconic River waterfront and downtown restaurants to local attractions and entertainment. The surrounding area is also known for its farms, vineyards and seasonal produce, bringing the flavours of Long Island into the experience.
Venture farther along the North Fork, where vineyards, farm stands and maritime communities sit between Long Island Sound and Peconic Bay. Discover places such as Mattituck and Greenport, enjoy locally produced wines and food, or simply spend time beside the water soaking up the character of this quieter corner of the island.
Long Island’s East End is also about life on the coast. Enjoy time on the beach, discover harbours and waterfront communities or arrange an excursion to experience more of the island’s Atlantic shoreline and famous Hamptons.
With an entire week based in Riverhead, there is no need to fill every day. Mix days out with time to enjoy your surroundings, revisit favourite places or simply relax. Local rail services, taxis, rideshares and organised excursions can help you experience more of the East End without needing to hire a car.
Whether your interests lie in wine and local food, beaches and coastal scenery, small communities or simply enjoying a more relaxed contrast to Manhattan, these six days reveal another side of New York that can feel a world away from the city.
Enjoy a final morning in Riverhead before making your way to the station and boarding the Long Island Rail Road for your journey back towards New York City.
Depending on your onward travel arrangements, continue to the airport for your flight home or add extra nights in New York City before returning to the UK.
Not Ready to Head Home?
Your journey doesn’t have to end here. Extend your stay with additional nights in New York City or speak to a Discover North America Travel Specialist about combining this holiday with another destination in the USA.
From the excitement of Manhattan to a full week experiencing the vineyards, coastal communities and relaxed character of Long Island’s East End, this rail-based journey offers two very different sides of New York without the need to hire a car.