Fly into your chosen New York airport, collect your bags, then transfer independently to your Manhattan hotel. We’ve suggested the iconic New Yorker, but other options are available.

New York City is renowned for its iconic skyline dominated by skyscrapers like the Empire State Building and One World Trade Centre. It is also famous for its cultural landmarks such as Broadway’s theatres, the Metropolitan Museum of Art, and bustling Times Square.

Once you have settled into your hotel, head out to experience the energy of the NYC for the first time!

The New Yorker Hotel or similar

Where better to get your bearings in NYC than at the top of one of the city’s towering skyscrapers?

The most famous is the Empire State Building observation deck, for views you’ll recognise from many a movie! The Edge, at 30 Hudson Yards, has a unique triangular viewing deck, and a glass balcony through which you can see the city streets100 floors below! Summit One Vanderbilt combines skyscraper views with futuristic mirrored art installations.

Once you have seen the whole of Manhattan from a birds-eye view, you will be ready to explore from ground level.

Optional Experience – New York Hop-on Hop-off Bus Tour
With stops at 30 key landmarks all around New York City – an easy way to get around.

The New Yorker Hotel or similar

You have the whole day today to explore Manhattan and beyond. You could choose to begin at Central Park for a guided walk or bicycle ride around the gardens. A visit to the Metropolitan Art Museum (The Met) will reward you with world-class works from the world’s most famous painters. Alternatively you could enjoy some world-class window browsing in all the shops along Fifth Avenue.

From further downtown you can visit Wall Street or catch the ferry from Battery Park to the see the Statue of Liberty up close. You could combine that with a poignant visit to the museum on Ellis Island, that tells the many stories of New York’s early immigrants.

End the day up in Midtown where you can enjoy the bright lights in Times Square or go and catch one of the incredible shows on Broadway.

The New Yorker Hotel or similar

This morning we leave the city behind and head to the far end of Long Island, so enjoy the coastal scenery.

After checking out of your hotel, transfer back to the airport to collect your pre-booked hire car (JFK Airport is on Long Island, so this airport works best). Once you have your car, head away from the city and up the southern coastline of Long Island.

As you leave the airport and head east, you’ll pass through Jones Beach State Park, well-known for its long stretches of sandy beaches and iconic boardwalk. This will set the tone for the next few days.

Continuing along the South Shore you can stop at the town of Babylon, which features waterfront parks and cozy cafes. At various points along the way it is possible to visit Fire Island, the large sand spit that protects Long Island. We recommend catching one of the ferries that regularly journey across to this (almost) car free island. The beaches are beautiful and a stroll along the boardwalks always reveals quirky artwork and beachfront cafés.

As you drive further east you will eventually reach the Hamptons, the epitome of luxury and laid-back leisure. Both Southampton and East Hampton are worth visiting for their boutique shops, art galleries and restaurants. You can always spend time celebrity watching too.

As you approach Montauk, today’s final destination the sea views remain breathtaking and the towns take on a more surfer vibe. Your beachfront hotel will be awaiting you arrival.

New York City > Montauk | 106 Miles

Marram Hotel, Montauk or similar

Perhaps start your day by visiting Montauk Point Lighthouse, even if you can’t quite make it for sunrise, you can still take in the dramatic views of the Atlantic Ocean and Block Island Sound. You can also visit the lighthouse museum that showcases the area’s rich maritime history.

Later in the morning you can head to Shadmoor State Park for a scenic hike along the cliffs. As well as the fresh sea air, you will be able to enjoy the ocean views and explore the old military bunkers. After your walk head to The Dock in Montauk for some fresh seafood.

The afternoon you spend relaxing on Ditch Plains Beach. It is a popular surf spot, so you could try taking some lessons at the local surf school or just sunbathe on the soft sand. If the beach is busy then you can also go to Hills State Park where the beach is usually quieter.

For evening dinner you may like to drive to Gosman’s Dock to dine by the waterside, or just enjoy the sunset at Montauk Harbour.

Marram Hotel, Montauk or similar

Start your day by driving west along the coast towards Amagansett and East Hampton. In Amagansett, you may like to stop for breakfast at Jack’s Stir Brew Coffee, or pick up fresh goods from Amber Waves Farm.

Then continue on to East Hampton, known for its elegant shops, designer boutiques, art galleries and residential homes. Perhaps take a leisurely stroll along Main Street, grab a coffee, and visit the Guild Hall, which hosts regular exhibitions and performances One of the many famous residents of East Hampton was the painter Jackson Pollock and it is possible to take a tour of his former home.

Southampton also has grand estates, such as the 19th century Rogers Mansion, which is now part of the Southampton History Museum and similar to East Hampton, Southampton’s Main Street and Jobs Lane offers a mix of designer shops and local boutiques. Southampton also claims one of the top rated beaches in America. Coopers Beach has soft white sands, gentle breakers and stunning views out across the Atlantic. It is perfect for a swim or a stroll along the shore.

In the evening you may enjoy dining at 75 Main, a spot with a lively atmosphere, or you can head back to East Hampton for a fine dining experience at Nick & Toni’s.

Marram Hotel, Montauk or similar

Although you will be flying home this evening, you still have plenty of time to continue exploring Long Island  on your way back to the airport.

After checking out of your hotel, we would recommend a visit to Sag Harbor, a picturesque village with maritime charm. Walk around the harbour and visit the Sag Harbor Whaling & Historical Museum to learn about the town’s seafaring past. You can also enjoy some wine tasting at Wölffer Estate Vineyard, a renowned local winery with beautiful vineyard views.

If you prefer to continue exploring the coast then Cedar Point County Park has some lovely coastal trails that lead to a lighthouse, that are well worth exploring. Further along the coast you may like to detour out to Fire Island Wilderness Visitor Centre (which can be reached by car) where you can explore the High Dune WIlderness and the trail to Old Inlet which is worth the effort.

Ultimately, you will need to return your car back at the airport, and check-in, in time for this evening return flight, or your onwards journey.

Montauk > Airport | 106 miles