Five great days in New York City

November 15, 2019

New York

So, you finally made it! Got these plane tickets and here you go. On your way to the city number one in the world. You feel excited!

You’ve been dreaming about this trip since you’ve heard for the first time the song about the “concrete jungle where dreams are made of”. 🎶

But then you realize that you don’t know that much about New York City beyond what you’ve seen in the movies. You may have a vague idea of what you want to see. Heck, you might have even already booked a hotel to stay at!

Your trip is almost here and you start getting stressed out as you frantically search the web for “the things to do on your first trip to NYC” and you just get overwhelmed by the sheer amount of the things to consider. Should I book that sail trip? Do I need to get the city pass? Brooklyn or Harlem for the night out?

Luckily, here I am to help you plan and organise your trip, so that you can relax and enjoy your visit.

Below you can find my five days itinerary to spending five fabulous days in New York City:

My best tip for visiting such a big city is to visit only one district per day.

You can even go more extreme and switch hotels every couple of days, once you’re done exploring the area. Personally, I realised it is much more efficient as you do not waste your time commuting from one place to the other. Plus if you need a quick break in the middle of the day at your hotel, not a problem - it is a max 15mins’ walk away!

Day 1 Upper East and West Side

This might be my favourite part of the city. I got swept away by its elegance and chic. It is a home to Museum Mile (the greatest museums in the city, such as the Guggenheim Museum, Metropolitan Museum of Art, the Museum of the City of New York), restaurants and shops.

Stay in one of many fantastic hotels that this side of the city has got to offer. Wake up early next day and head straight to get the breakfast to go from the famous Levain Bakery. If standing in the line is not your thing, and you want some truly great Australian coffee experience, do visit Hutch+Waldo. Both of these are in close proximity to the Central Park, your first day’s main destination.

Central Park

There is so much to do and see in Central Park that it depends on how much time you want to spend there. You can rent a bicycle to be able to explore everything this park has to offer. I would also recommend taking a free tour of Belvedere Castle. Even if you don’t go inside the castle, the views from up there are truly beautiful and you can walk there through Stawberry Fields where you will find the famous “Imagine” memorial, a tribute to John Lennon. Then walk around The Lake, across the park’s famous Bow Bridge and head towards the castle.

One of my favourite relaxing points was near Umpire Rock right before continuing on to 5th Avenue, where you can do some shopping or visit the iconic Tiffany’s, especially if you’re Audrey Hepburn fan.

New York

Once you’re done with shopping, take a moment to relax over dinner at Jacob’s Pickles and check out the schedule of Lincoln Center. Maybe you will find some ballet, opera or jazz performance for the evening there. I fell in love with the magic of the center and its surroundings. Worth a stroll!

Lincoln Center

Day 2 Midtown

You can start the day a little later with a brunch at Tartine. Once satisfied, visit Washington Square Arch and then stroll around West Village’s designer boutiques and trendy restaurants.

As the streets blend with each other, you will probably find yourself at “The Village”. Greenwich Village is the home of the bohemian culture and associated with the start of the LGBT movement. I would recommend paying a visit to The Stonewall Inn and learn about its history.

I love the independent spirit of this part of Manhattan. Not to mention that it all reminds me of my favourite show, Friends. Speaking of which you should visit The Little Owl that is located at 90 Bedford St, right underneath the apartment from the very show!

After that, you can head for coffee at Nith Street Espresso and you will find yourself at the famous Chelsea Market. I could speak for hours about the choice of things you’ve got to do here, but TimeOut has already done it for us.

And then pay a visit to St. Patrick’s Cathedral. Whether you’re religious or not, the architecture and atmosphere of this building is soothing and provides a fantastic break from the crowds on the streets right outside.

St. Patrick’s Cathedral

If it is a clear day, I would recommend booking your visit to Top of the Rock observatory for the evening. It is located on top of Rockefeller Center and offers unforgettable views of the city skyline. If I were to choose between this or Empire State Building’s visit, I would always choose the former, because you get to see the latter!

Top of the Rock

If the weather is not on your side, come back here another day and instead, go and see a Broadway show. It is best to purchase your tickets at TKTS booths, where you can buy the same-day show tickets even 50% cheaper. There are two TKTS booths in your vicinity, either at Times Square or Lincoln Center.

Day 3 Midtown Part 2

This day will be a little less full on. You can go and visit Empire State Building in the morning for the daylight NYC skyline’s view. Just make sure to buy your tickets in advance with skip the queue option, or otherwise you will waste too much time with the relentless crowds.


Then continue towards the New York City Library, passing through the Grand Central station on your way. Stop here to take a photo of its famous ceiling.


Grab a lunch at Bryant Park Grill or Koi and then devote a couple of hours for the library itself. Its architecture is truly stunning, especially the main reading Rose Room. You will see people studying, working, reading books and if you’re anything like me, you’d just want to move in to New York this very same day and imagine yourself coming here every weekend.


Relax with a cocktail at Lillie’s Victorian Establishment and visit Times Square all lit up in the late evening.

Day 4 Lower Manhattan

Start your day with a coffee at Bluestone Lane Water Street Coffee Shop and head over to 9/11 Memorial. You will most likely pass the Oracle building on your way there.

oracle building

The atmosphere surrounding the whole area is one of reflection. As per the design of the two “Reflecting Absence” pools cover the area where the Twin Towers used to stand.

If you wander around the pools, you will notice some white roses left on certain names inscribed at the pools’ murals:

An idea from a volunteer in 2013 has become another way for visitors to learn about the victims, share their experience and connect. Before opening to the public, 9/11 Memorial Museum staff places a white rose at the name of each victim who has a birthday that day.

Inscribed on the 9/11 Memorial are the names of the 2,983 victims of the 1993 and 2001 attacks. Every morning a staff member checks a binder located in the 9/11 Memorial Museum that has each name and birthday listed chronologically. A white rose is cut two inches below the leaves and then placed at the name on the parapet.

reflecting absence

This memorial is essential viewing for any visitor to New York and whether you like it or not, it will transport you back to the time and place where you were at the time you heard the news about the attack on that September day, 2011.

For the late lunch stop at Trinity Place or Augstine. I found these to be uniquely suiting the atmosphere of FiDi.

From there, you can head towards Wall Street to see the famous exchange as well as the Charging Bull and Fearless Girl statues. Then progress towards Battery Park. See SeaGlass Carousel and wander around to admire the beautiful waterfront and flower gardens as well as multitude of sculptures:

Battery Park

For the late afternoon/evening entertainment book the Hudson River Sunset sailboat trip with Manhattan by sail in advance. I loved this trip not only for the breathtaking sunset views but also the great crew and delicious food offered:


Day 5 Brooklyn

Visiting New York City does not equal to visiting Manhattan. That is why do make an effort to explore the districts outside too, such us Queens, Harlem or Brooklyn. Since we are in Lower Manhattan, the closest neighbourhood for us to get to is Brooklyn.

We will cycle across the famous Brooklyn Bridge, stop there for a few photos opportunities. And then head to Brooklyn Botanic Garden for a couple of hours.

If you’re in the area on Saturday, do head over to Williamsburg for Brooklyn Flea market.

From there do see Wythe Avenue murals and head over to Brooklyn Heights for a drink with a great Manhattan views.

Take a couple of hours to rest and either go out in Brooklyn or head over to the other paet of the city, Harlem, for some jazz.

So there you go! No need to worry about your trip anymore. And sure, I do realize we might have different taste, and you might want to do some more of that than what I did, but following the tips in this guide, you will notice how much more you will be able to see and enjoy it as opposed to spending your precious vacation time in the New York traffic.