New York City – A Five Day Itinerary

In 2009, I started another five week trip after my successful stint in South East Asia. The trip started at the end of December and lasted until the end of January 2010. The reason my friend and I started at the end of 2009 was so that we could have a five day stopover in New York City to see the ball drop at New Year’s Eve.

It goes without saying that I really wanted to see the main sights of New York City as well, since this was my first visit there. However, New York in December is freezing! We had packed for Middle America which would be warm so we didn’t spend that much time sightseeing outside. Most of our time my friend and I spent indoors in cafes and restaurants. To give you and idea what New York looked like during my stay there, I have added the photo below. In this post, I’ll describe the main sights and the main impressions of my five day stay.

New York City

New York City

Day 1

Empire State Building
Most of our first day consisted of the visiting the Empire State Building. A must-see when you’re in the city for the first time. The queues inside are hilarious. They look the same way as the ones in amusement parks, because whenever you think you’re done because you’re at the end of a room; another room with a similar structure pops up. At the end we spent over an hour queuing. It was certainly worth it though. The views over New York City and Manhattan in particular are quite impressive. I’ve climbed atop a lot of churches in Europe but nothing I’ve seen beats the view from the Empire State Building. We went to the 86th floor observation deck. If can really recommend a skip-the-line pass which you can get from Get Your Guide, trust me, otherwise your whole day will be spent at this one building.

New York City

New York City

Times Square and Fifth Avenue
After the Empire State Building, we walked to Times Square and Fifth Avenue (the shopping street). Absolute madness! Maybe because it was December, or maybe it’s the same always but it was so crowded that it wasn’t nice to walk around.

New York City

We had a look inside the New York Public Library on Fifth Avenue (I’m obsessed with books so I couldn’t miss this).

New York City

New York City

When you walk around these main areas of New York (Times Square in Manhattan for example), you cannot see the buildings at all. It’s actually shocking to think of the amount of work that must’ve gone into hanging and renewing all the billboards in the city.

New York City

New York City

On one cold winter day we decided to watch Sherlock Holmes in the cinema. Could this have been because of the huge billboards we walked past everyday?

New York City

Day 2

Staten Island
Another frequently visited sight in New York is the Statue of Liberty and Ellis Island. Instead of traveling there directly and visiting them, we decided to take the free ferry from Manhatten to Staten Island. From the ferry you can see these sights. I only managed to take a few photos because I had to continuously shove my hands in my pockets. It was absolutely freezing.

New York City

New York City

Next time, I would like to spend a bit more time visiting these sights. Especially, Ellis Island sounds incredibly interesting.

Day 3

Central Park
When you talk about New York City, people think of a lot of different places. Empire State Building, Times Square, Statue of Liberty and also.. Central Park. I think the best time to visit the park would be in spring and summer when you can sit outside on the grass to enjoy an ice cream or some coffee. In winter it’s not so bad either though. The trees are bare, but the ice rink looks fun.

New York City

New York City

New York City

New York City

Bloomingdale’s is right next to Central Park and it’s a great place to warm up and do some shopping.

New York City

We spent almost an entire day exploring these two places.

New Year’s Eve Ball Drop
The reason we visited New York was to witness the famous ball drop on Times Square. We left the hostel at 6pm, when we arrived on Broadway it was already super busy! The way it was arranged is that you move from area to area in a “controlled” way. NYPD stops a group of people at every barricade and when the next area has cleared up your group can move. This movement unfortunately was not very controlled. People started to rush through the barricade and everyone was pushing to get through. A bit silly since everyone of the group would get to the next area and the areas following it. Times Square is on 42nd Street and we made it to 53rd Street. This means that if you want to see the ball drop you really have to be on time and arrive at least in the afternoon. Unfortunately, New Years Eve is not in the summer (in our hemisphere) so it was -4 degrees C. My friend and I decided to jump the barricade and to hide out in a cafe. After the cafe we snuck back into the barricade to wait the last few minutes until the ball drop. From a distance the ball drop does not look very spectacular. It’s a very slow 43m descent, but the fireworks that followed it from both Times Square and Central Park were worth the experience.

This was fun, but to witness a ball dropping with -4 degrees C should only be done once.

New York City

New York City

Day 4

Brooklyn
My favourite area in New York City is Brooklyn. It feels like what the real New York City should feel like if it wouldn’t have been so touristy. One night we went out in a very cool bar in Williamsburg with a nice bartender and his best friend who just returned from the army.

The day after New Years Eve we visited Brooklyn again to walk around all day to take in the atmosphere. It’s so much more quiet than Manhattan. Pure bliss.

New York City

New York City

Brooklyn Bridge
The best way to get from Brooklyn to Manhattan is by taking the gorgeous Brooklyn Bridge. The views of the skyline from this bridge are magnificent.

The first four pictures are of Manhattan Bridge which you can see when you walk over Brooklyn Bridge. 

New York City

New York City

New York City

New York City

New York City

Day 5

Harlem
One day we tried to reach the hostel by metro from Manhattan and we accidentally ended up in Harlem. I wasn’t too happy about this situation because I had heard so many bad stories about the place. However, people are so friendly and just like when we visited Brooklyn we felt like we were in the real New York when we walked around Harlem. I would love to visit this neighbourhood a bit more next time around.

Greenwich Vilage
Greenwich Village is another one of those nice areas in New York City that’s worth a visit. It has a lot of cute little cafes and old family companies. It’s great to walk around Greenwich Village for a while and to enjoy a coffee in one of the local cafes.

New York City

Conclusion

New York City is a fantastic place to visit. I do regret the timing of our visit and the preparation of our stay. Since we were moving on to warmer climates, we didn’t bring any winter clothes so it was too cold to be outside for too long. And since New York City has a lot of nice areas to walk through (Brooklyn, Greenwich Village, but also Central Park) it would be better to visit in spring or autumn. These are also the best places to visit in general because I’m not too fond of Manhattan; there are too many billboards and too many people for it to be enjoyable. I’ve edited this post in 2020 and there’s a lot I would do differently nowadays, but most of the main sights are still the same. I can’t believe I haven’t visited the USA after this short visit to New York!

Please note, this post contains affiliate links, which means I receive a small commission for purchased goods/services at no extra cost to you. Thanks for supporting my writing!

Print Friendly, PDF & Email

4 thoughts on “New York City – A Five Day Itinerary

  1. That’s awesome that you actually went to NYC to see the Times Square Ball Drop for New Year’s Eve! I have been meaning to do it for years, but have never formulated any concrete plans to date. You are right about visiting NYC in the warmer months, though. Such a beautiful city for walking and people watching if that suits your travel style.

    1. The ball drop is indeed one of those things that should be experienced once in a lifetime! I would love to return to the city in spring or autumn. I think Central Park would look the best when the foliage is orange coloured! One day… 🙂

    2. If you do go back to NYC for an Autumn trip, then I highly suggest going in late November to time it with the American Thanksgiving Weekend. I have yet to blog about my experience there in November 2011, but the weather was unusually warm (we could wear t-shirts at Times Square on our last night) and the Macy’s Thanksgiving Day Parade is definitely a once-in-a-lifetime experience worth checking out!

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.