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5 day itinerary for New York City


New York has got some of the most iconic sights anywhere in the world, and a five night break will give you ample time to check out many of the fantastic things on offer.

This is the itinerary from my recent trip to NYC, we stayed in Midtown Manhattan which was an ideal base. We were very lucky with the weather for the time of year, enjoying wonderful sunshine for all but one morning of the trip when we had a little rain. It’s best to save museums and shopping for any wet days, as Lady Liberty is best enjoyed in beautiful sunshine if possible. Each day can be switched around if you like, but this should give you some ideas for your trip.

Day 1

9/11 Memorial and Museum – Catch the bus downtown to see the Flatiron building on your way.

Lunch at 225 Bistro Oliva – Grab a slice of pizza at this market/deli near city hall.

Times Square – Head back up towards Midtown to enjoy your first glimpse of Times Square by day. Do a spot of shopping whilst you’re at it.

Cocktail hour at Top of the Strand – Visit your first NYC rooftop bar at one of the city’s best, Top of the Strand and enjoy the stunning views of the Empire State Building.

Dinner at Frankie & Johnnie’s Steakhouse – Enjoy wonderful steaks, burgers, seafood and pasta in a John Barrymore’s former townhouse. The burger was excellent!


Day 2

Statue of Liberty – Head to Liberty island on the ferry, enjoying magnificent views of Manhattan from the boat. Once you’ve finished admiring the Statue of Liberty, head over to Ellis Island to see the halls where 12 million immigrants passed through between 1892 and 1954.

Grand Central Station – On your way back uptown, marvel at the iconic architecture of Grand Central Station. You won’t need long to enjoy this attraction and it doesn’t cost anything, but it’s well worth a visit.

Lunch at Morini – this upscale Italian restaurant on Madison Avenue offers a fantastic three course lunch for $39 a head. The decor is beautiful, the service excellent and the food is exceptional. Save room for dessert because the Torta Di Cioccolata is not to be missed!

Quick walk around Central Park.

Hockey at Madison Square Garden – The New York Rangers played at home against the Washington Capitals. It’s a brilliant experience to visit the stadium and enjoy the game alongside home fans.

Times Square – By night, Times Square really comes into it’s own. If you’ve still got the energy after the hockey it’s great for some evening shopping or a cocktail atone of the bars.

Day 3

Natural History Museum – Head to the museum to explore the wonderful exhibits of all the world’s best creatures. Don’t leave without checking out the room with the blue whale.


Central Park – An afternoon stroll around Central Park is lovely after a trip to the Natural History Museum, it’s literally across the street so you won’t need to go far. The south of the park hosts most of the famous sites such as Bow Bridge, Bethesda Terrace & Fountain and The Mall, so I recommend exploring that first.

Harlem – Take the bus around outer Central Park to explore Harlem, where you’ll see the Apollo Theatre, Grant’s Tomb and the beautiful gothic Cathedral of Saint John the Divine.

Dinner at Café China – Michelin-starred Midtown Sichuan restaurant Café China offers wonderfully authentic cuisine at reasonable prices. Make sure to book or arrive early in the evening as the restaurant is very popular.

Jazz at Fine & Rare – With impressive decor and an exceellent cocktail menu this restaurant and bar is a good choice to enjoy some live jazz after your evening meal.

Day 4

Top of the Rock – The view from the Rockefeller Centre is truely spectacular, with Central Park on one side and views stretching across downtown Manhattan and the Hudson River on the other. We chose this over the Empire State Building so that it’s iconic art deco design could be part of the view.

Shopping – Rockefeller Plaza and 5th Avenue are home to some of the best shops in Manhattan, make sure you leave some time to visit the stores here.

Lunch – Grab a slice of pizza on 5th Avenue in between shopping.

The High Line – This unique park is 1.45-mile-long and transforms an disused railway track into the ultimate urban sanctuary. Elevated over Manhattan’s Upper West Side it also has a beautifulviews of nearby streets all along it.

Cocktails at Bar 54 – Manhattan’s highest rooftop bar has a lovely cocktail menu and amazing views of the Chrysler Building and Times Square. The balcony even has igloo-like bubbles where you can enjoy your drinks sheltered from the winter cold.

Day 5

Brooklyn Bridge – Built in 1883, the Brooklyn Bridge is a cabled suspension bridge that is wonderful to walk over and enjoy views of Manhattan, Brooklyn and the East river. A historic New York City landmark which transports you back in time.


Lunch at Keen’s Steakhouse – Wood pannelled decor and crisp white tablecloths greet you as you enter Keen’s. The service, food and atmosphere of the place are all excellent. As our final lunch in New York we couldn’t fault the sirloin steak with fries and chocolate cake for pudding.

That’s all for now, I hope this itinerary will give you some ideas for a trip to New York City.

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