Five Days in New York: How to Successfully Plan Your Time and Spend It With Pleasure

9:57 am  |  30.06.2021

If you are only in New York for two or three days you ask yourself the question: What is really worthwhile and should I just not miss it?


Even if you have “only” 5 days for New York, it is definitely worth the trip. With the right planning, you can then manage to see the most important sights, go on great tours, shop, and still have a little time for yourself.

Day 1: Arrival

After the transfer to the hotel, the first path always leads to a cafe for a coffee. This gives us enough energy for the day (at least for the first few hours). Finally, don’t underestimate a time difference of at least 6 hours. Today the whole point is to “come” without big meetings. The best way to do this is to take a walk around the city. See where there are good eateries or bars and grab the New York Pass or Explorer Pass. Then you can start right the next day.

If you’re still in good shape in the evening, take a stroll around Times Square and have a drink at one of the rooftop bars. For example, Skyroom-Bar or “BAR 54” at the Hyatt Times Square hotel.

Day 2

The day starts very relaxed with breakfast – either in your hotel or in one of the many dinners in the city. Then the city is explored. For example, you can do the downtown tour with the hop-on-hop-off bus (included in the New York Pass and starts in Times Square) and do the whole round once (takes about 2 hours). The guides are super-funny and you get a great overview of the city.

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Then in the afternoon to the American Museum of Natural History and explore the adjacent Central Park (there are plenty of cool shopping spots on 5th Ave on the way from Times Square). In Central Park, you can also rent a bike and see a lot in a short time. Stay where you like it best and enjoy the impressions.

In the late afternoon, you can go to the “Top of The Rock” – the viewing platform from Rockefeller Center to admire New York by day and by night. 

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Take 2-3 hours for this, the change from light to sea of ​​lights is awesome. Depending on what you prefer, you can either go to the rooftop bar “The Peninsula” or to Bill’s Bar & Burger, which can also be found directly opposite.

Day 3

First, you go west to the Hudson River and there to the Pier of Circle Line Cruises to do the big Manhattan boat tour (Full Island Cruise, takes 2.5 to 3 hours).

You drive once completely around Manhattan. Back again it is not far to the northern point of the High Line Park. 


You walk all the way to the end in the Meatpacking District. You can strengthen yourself either in the restaurant of “The Standard” or you go two blocks to the Chelsea Market. From there, orientate yourself 4-5 streets south, there are many spots & bars that are really nice.

From here it goes west (the fastest way is by subway) – destination: the Brooklyn Bridge. Now walk over the Brooklyn Bridge and off to Brooklyn Bridge Park. 

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There you can also explore the district for yourself – you can relax and take the subway back to Manhattan. Be sure to visit the Brooklyn Ice Cream Factory.

In the evening you should go to the Empire State Building. It is best to plan this position for Thursday, Friday, or Saturday. Because then from 10 p.m. a saxophone player will play on the viewing platform. Then you can end the day with a few drinks at the rooftop bar 230 Fifth – from here you have a wonderful view of the Empire State Building.

Day 4

Today you head south, walking towards Madison Square Park and the Flatiron Building. There’s one of the best burgers in town right in Madison Square Park: Shake Shack Burger.

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Continue towards Union Square. There are many great shops and bars along the way. And 5 blocks to the south, you’ll find yourself in Washington Square Park and Soho, a beautiful part of town! From here you would go to the Financial District. On the way, you also pass Ground Zero with One World Trade Center, then to St Paul’s Cathedral and Wall Street to Battery Park. From there take the Staten Island ferry!

If you’re back, we recommend Pier A Harbor House for its strength. It’s nice to walk north again, right up the Hudson. There’s Shake Shack Burger again or two culinary masterpieces with Mexican El Vez right next to Ground Zero.

In the evening, you can visit the One World Observatory from the One World Trade Center and then plunged into one of the sports bars in the East Village.

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5 Days of New York: the Last Day and the Way Back

You should leave Manhattan approximately 4 hours prior to departure so that everything runs smoothly at the airport. Until then, you can use half a day. We wouldn’t plan anything, just go where you like best.

Our Tips

  • Even if it is attractive to plan the 5 days in New York with the many sights, spots, and tours, our tip is that you leave at least half a day completely free.
  • Try to book the flights so that you fly overnight and arrive in New York very early.
  • Budget tip: There are various sightseeing passes that not only save you up to 36% on all tickets but also avoid many queues (such as the New York Pass or Explorer Pass).

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