July 1, 2019

4 Days in New York City: The Ultimate City Break Itinerary

Last month I visited New York City for a whirlwind 4-day bucket list trip and I’m still obsessing over it. Nothing compares to the Big Apple! This was without a doubt the best city break we’ve ever been on.

Being such a major city, there’s way too much to fit into one trip. But that doesn’t mean you can’t see most of the key sightseeing spots! So here’s the ultimate itinerary to help you see the best of New York City in just four days.

Read more: How to plan a trip to New York City

Day One: Midtown Manhattan & Chelsea

The Flatiron Building

I bet you recognise this spot! The Flatiron Building made a great first stop for us as it was only four blocks from our hotel. You can’t go inside but it’s great to see, and of course get a few photos.

Madison Square Park

Right next to the Flatiron Building is Madison Square Park. It’s a pretty small area with only a pond and a Shakeshack, but it’s a really nice part of the city to wander through.

Chelsea Market

Make your way over to Chelsea Market to grab a bite to eat and enjoy the different shops and stalls. It’s pretty busy here but has a great vibe! It’s the ultimate spot for foodies.

The High Line & The Vessel

Once you’ve refuelled, head down to the starting point of The High Line and embark on the 1.45-mile-long stroll above the city. You can start your walk at either end, but I think it’s best to finish at the newly opened Vessel structure. Made up of 2500 steps, this sightseeing spot is new to New York City in 2019 and offers an amazing city view. You’ll need to book your tickets in advance as they sell out fast on the day.

Hudson River Park

Wander down the last part of The High Line from The Vessel to the water’s edge. You can stroll along the shoreline of the Hudson River and enjoy time in the park. This is where a lot of the helicopters land, so you may even spot a famous!

As it’s your first day you’ll no doubt be shattered come the evening, so head back in the direction of your hotel and find a great place to eat on route.

Day Two: Lower Manhattan, The Islands & Brooklyn Bridge

One World Trade Centre

After breakfast, make your way over to the One World Trade Centre. This is a spectacular building from the outside, and a huge underground shopping centre on the inside. If you wander right the way through, you’ll find yourself at your next stop.

One World Observatory

The One World Observatory gives you a fantastic 360-degree view of the city, which is no surprise as it’s seriously high at 102 stories (which you reach via lift in just 47 seconds!). You can buy tickets here or get in for free with a NYC Sightseeing Pass.

911 Memorial

After the Observatory, make your way down to the 911 memorial. This is a poignant place, but somewhere you need to see. It is such a beautiful memorial to remember those who lost their lives on that day. If you have time, you can also visit the museum nearby.

Statue of Liberty & Ellis Island Ferry

Continue down towards Battery Park and grab a bite to eat, before catching the ferry over to the Statue of Liberty and Ellis Island. You can do this for free with the NYC Sightseeing Pass. Make sure you leave enough time for this as you’ll have to queue each time you want to get on and off the boat!

An alternative option is to get the free ferry to Staten Island, which gets you a little closer to the Statue of Liberty without stopping on the island. There was absolutely no queue for this when we went.

Wall Street

Once you depart the boat back at Battery Park, stroll up to Wall Street and stop by the New York Stock Exchange for a quick photo.

Brooklyn Bridge

Make your way across Brooklyn Bridge during golden hour for the dreamiest views of the city skyline. It’s crazy busy though, and don’t step in the bike lane. You will be shouted at!


Finish your Brooklyn Bridge experience in Dumbo with a delicious pizza from Julianas. The queue can be quite long though, so bear that in mind. If you don’t fancy waiting, there are plenty of other spots to dine.

You can either take the ferry back to Manhattan, walk back over the Bridge or grab an Uber like us.

Day Three: Upper Manhattan, Central Park & Fifth Avenue

Top of the Rock

Start your day bright and early at the Top of the Rock, aka the Rockefeller Centre. A trip to New York City isn’t complete without it! The panoramic views across Central Park on one side and over towards the Empire State Building on the other side are out of this world. On a good day you’ll even see all the way down to the Statue of Liberty. You can get up here for free with the NYC Sightseeing Pass.

Central Park

When you’re back down on the ground, make your way over to Central Park and spend a few hours exploring the hidden gems that this peaceful part of the city has to offer. On a good weather day, this is a great place to rent a boat on the lake. If you have kids, why not take them to the zoo?

MET Museum

If you’re into your art or just fancy seeing where all the celebs go for the MET Gala, stopping by The Metropolitan Museum of Art is a good idea. You can get in here for free with the NYC Sightseeing Pass.

Fifth Avenue

You’ll find yourself on Fifth Avenue by this point so wander back up the side of Central Park to see Trump Tower, Tiffany & Co. and the countless designer shops. This is a good spot to find some dinner too.

Day Four: Midtown Manhattan, Broadway & Times Square

Empire State Building

If you’re craving more views over the city, head up the Empire State Building. We decided not to as the views are better from the Top of the Rock, but it’s worth passing by to see it from the ground at the very least.

Chrysler Building

As far as I know you can’t go inside, but this is another building you should see up close during your trip. In my opinion it’s the best-looking skyscraper!

Grand Central Station

It’s time to see where the Madagascar crew caused havoc! Avoid Grand Central Station at rush hour, but definitely go inside for a look around. There’s a food court underground too which would make a good lunch stop.

New York Public Library

This was closed due to a public holiday when we were there, but even if you don’t go inside, you have to see it from the outside! For a minute I felt like I was in The Day After Tomorrow – minus the flooding crisis.


Grab yourself some cheap tickets to a show on Broadway! You can queue at the TKTS stand in Times Square for discounted tickets to so many shows. We decided to get tickets for Beetlejuice 20-minutes before it started and it was AMAZING. You can always get tickets to an evening show if you’d prefer.

Times Square

As the sun begins to set, make your way over to Times Square to see it come to life. It’s worth seeing in the day and at night in my opinion, but of course it is best when the screens illuminate the entire street. There’s no way to explain what it’s like, you just have to see it!

Hell’s Kitchen

End your evening with a spot of dinner and drinks over in Hell’s Kitchen. There are so many great restaurants to choose from in this part of the city.

And that’s four days in New York City done and dusted!

This itinerary is busy, but not chaotic, so you’ll still have plenty of time to explore other areas and enjoy some great food. And be sure to play around with the itinerary as everyone will be staying in a different part of the city.

Follow my route

Heading to New York City soon? Save this map to use whilst you’re there!

Simply click the star icon to add it to your collection. To find it again, open the left-hand tab in Google Maps and click Your Places > Maps. 

New to this tool? Learn more about My Maps in this post.

Read more: Cheap eats in New York City

Have you been to New York City? Would you add anything else to this itinerary?

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