Your 5 Day Itinerary in New York City

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Everybody dreams of visiting New York, but with so much to do it can be overwhelming to try and plan a trip there. I’ve visited a handful of times now and I’ve compiled my favorite things to do in the city. It doesn’t matter what season you visit, New York is wonderful in them all.

I do have to say, early June has been my favorite time to visit so far. All week the weather was around 70 degrees and mostly sunny – perfect for popping around the city! Of course New York at Christmas time is magical, and in the spring it’s lovely too. You just can’t go wrong.

The best way to organize your trips is by location in the city. You can do much more if you focus each day in a specific borough or neighborhood.

Day 1: Midtown

There is something spectacular about Midtown. It’s very popular and filled with tourists (but let’s face it, so is the rest of New York). It also hosts some of the most iconic parts of New York City, which is why it’s a great place to start.

Grand Central

Take the subway to Grand Central terminal. Make your way up top to the elegant station and take in the view of the constellations on the ceilings and watch the daily comings-and-goings of New Yorkers. You can even have a drink or grab brunch in the station’s restaurant.

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Rockefeller Plaza & Top of the Rock

This is a great spot all year long, although it is the best in December when the ice rink and the Christmas tree are up. But, even when you’re visiting in other months you can see exactly where they place the Christmas tree every year.

(I saw this on my first trip to New York City five years ago! I also saw the Christmas tree 3 years ago. Luckily my photography has improved a lot since then.)

christmas treerock christmas tree If you want the best views of Manhattan, you’ll want to pop up to the top of the Rockefeller building. It’s called the Top of the Rock and it’s about $45. Purchase tickets online ahead of time to skip the line! While the Rockefeller building isn’t as tall as the Empire State Building or the Freedom Tower, I suggest the Top of the Rock so that you can see the more iconic buildings in your photographs!


5th Avenue

Next it’s time to take a walk along 5th Avenue. It’s where you will find so many popular sights and stores like the New York Public Library, St Patrick’s Cathedral, Saks Fifth Avenue, Tiffany & Co. (which displays beautiful decorations each year at Christmas time) and the Apple store on 5th. This store is spectacular because the entrance to the store is in a glass building with a staircase that leads down into the actual shopping center. And, it’s conveniently located across from the Plaza Hotel.


Times Square

End the day in Times Square. I like to get here just before the sun is going to set. It’s amazing to see the transition from day to night. Grab a hot dog and a diet coke from a street vendor and find a spot to sit and people watch as the sun goes down.

You can also take photographs with people in costumes, but be warned that they expect tips! They are very pushy, and the first time my sister and I visited we were too young to realize they wanted money from us and then we found ourselves in a pickle because we didn’t have cash. If you don’t want to take photographs with them, be assertive and say no! Or ignore them the best you can.

You could spend hours here eating, shopping in the department stores and watching street performers. And at the end of the night, there’s a subway shuttle that goes straight to Grand Central terminal. From there you can get back to any part of the city!

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Day 2: The Financial District

This is where the money’s at – and it’s easy to tell. The tallest buildings, the cleanest streets and the most expensive malls can be found at the very tip of Manhattan. It’s a wonderful part of the city to explore, and it houses tons of attractions!

One World Trade Center & 9/11 Memorial

This is another place I’ve always wanted to visit, so when I came to the reflecting pool this week I felt like I could finally say I’d truly seen New York. This is a very somber and humbling experience, seeing the Freedom Tower rise above the New York skyline and the reflecting pool next to it disappearing into the ground. Each day the staff at the memorial place flowers on the engraved names for every birthday, a tradition I really admire.

I didn’t make it into the museum this time, but it’s on my agenda for my next trip into the city. I also did not go up in the Freedom Tower, but it’s the tallest building in New York so it would be worth it. Again, purchase tickets online ahead of time and skip the line.

Travel Tip: This is less of a tip and more of a request. The 9/11 Memorial is incredibly sentimental and extremely sad. Please be courteous to everyone around you and make taking pictures your last priority. The worst thing is seeing someone smiling next to the memorial taking a selfie.


The Oculus

This building is filled with expensive stores that you can window shop (or purchase!) and walk around. It’s also the entryway to the PATH trains to New Jersey. I love stopping in here and browsing through Kate Spade bags. It’s also a unique building just by its architecture and worth a stop in.


Staten Island Ferry

This is my favorite way to see the Statue of Liberty! Jump on to the Ferry and enjoy stunning views of Manhattan and pass right by the Statue of Liberty. This ferry has been around since the 1700s, although its much improved now for the thousands of people it transports every day between Staten Island and Manhattan.

Another thing you can do is take a boat ride around Manhattan. This is on my bucket list still, but I always hear people rave about these trips.

Liberty State Park

If you want to get up-close and personal with Ellis Island and the Statue of Liberty, you’ll want to cross over to New Jersey. The easiest way to get there is to take the Liberty Landing ferry ($7 each way) across to the park. From the ferry it’s only a ten minute walk to the state park. You can also see the Statue of Liberty from a distance on this boat.

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Wall Street

Take a walk down Wall Street to see the stock exchange. There isn’t much to do here but it’s an iconic spot to sight see. You can also find lots of places to eat in this area.

City Hall & Courthouse

If you’re a fan of Law & Order, you can’t miss the famous courthouse! I’ve been twice and it was impressive each time. It’s also very conveniently located near the Brooklyn Bridge.


Brooklyn Bridge

End the evening by walking across the Brooklyn Bridge. It’s usually crowded, but incredibly fun! You get a nice breeze walking over the bridge and you also get expansive views of both Manhattan and Brooklyn. It’s gorgeous to cross as the sun is setting. Once you get to the other side you can eat dinner in Brooklyn and then just hop on the subway to get home.

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Day 3: The Met

Yes, I have an entire day dedicated to an art museum. But that’s for good reason. The Metropolitan Museum of Art is massive, and it takes all day to get through it all. Despite my many trips to the city, I had never been here! It was the best treat, especially because the $25 ticket ($12 for students) is a 3-day pass and includes all three of the museums locations.

1st Floor of the Met

Don’t forget to grab a map when you get here because otherwise it’s easily to get lost. I looped around the first floor twice and still missed rooms! This floor has beautiful exhibits like ancient Greece (ah, a special place in my heart) and Rome; Arms & Armor which has incredible medieval armory; Egyptian Art; Arts of Africa, Ocean & the Americas; Contemporary Art; European Sculptures; and the American Wing.



After you tackle the first floor, take a break for lunch. You can eat at different cafes inside the museum. In the American wing you can sit in a gorgeous indoor courtyard and see sculptures and the outside of the home depicting old American Architecture (pictured above), but I suggest leaving the museum and taking a break out on the steps. There are tons of food vendors lined up outside the museum, and the front steps are a very popular spot to take a break and enjoy the view of New York. You could also walk behind the museum and enjoy lunch in Central Park for an hour or so.


2nd Floor of the Met

The second floor of the museum includes the American Wing (there’s also a bit more on the 3rd floor!); Musical Instruments; Asian Art; Art of the Arab Lands; Near Eastern Art; 19th and Early 20th European Paintings and Sculpture; Contemporary Art; and European Paintings 1250-1800.

There is also a special exhibit spanning both the first and second floor called Heavenly Bodies. This is a fashion exhibit inspired by the Catholic faith and is pretty controversial, but the display is immaculate. The lights are dark with spotlights on each mannequin, and there is dramatic music playing as you walk through each room. This floor is very popular because it has classic works by Van Gough and Monet, who is my favorite artist! I love Impressionism, so I spent a lot of time here. They currently have an exhibit called From Paris to Provence which even features some of Monet’s Water Lilies!


See a Show

The Met closes at 5 during the week, but is open later on Fridays and Saturdays. If you go during the week, you have plenty of time to grab dinner and relax for the rest of the evening, or you could do something fun. The app Today TIX is perfect for last-minute plans. You can buy tickets to Broadway shows, concerts, etc. I browsed through the category “What’s Weird & Wonderful in NYC this Week” and found a $10 comedy show! It was a riot and almost everyone there was a local. It was a nice change to do something that isn’t touristy.You just pick up the tickets at the box office and away you go! It was one of the highlights of my trip

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Day 4: The West Side

We will be making our way north today, starting in Chelsea and ending in Washington Heights. These are the highlights of the west side of the city.

Chelsea Market

The Chelsea Market is pretty well known and very fun! It can get crowded, especially at the restaurants and food vendors, so you have to be patient. This edgy market has exposed brick walls and a very industrial feel, but it’s filled with hip stores and food. There are big names like Anthropologie, and there are also small local shops selling books, souvenirs and even items from around the world. There is a store called Artists & Fleas which is a flea-market styled shop with local artisans selling their work! It’s one of the best shops inside.


Highline Park

This park is unique in that it’s build on old train tracks above the city! It’s a wonderful use of recycling old industry and turning it into beautiful green space for everyone to enjoy. You can catch views of the Empire State building from here and you can also scope out great restaurants and shops in the Chelsea neighborhood.


Alice’s Tea Cup

When you’re ready for a break, Alice’s Tea Cup is the perfect spot to rest and have afternoon tea. It’s located on 73rd Street. Just like in London, you can enjoy tea time in an enchanting room. I loved the decor of this place, and how each additional location is called Chapter 1, Chapter 2 and Chapter 3. I recommend ordering a cute tier of food to enjoy with your tea. You get to choose scones, finger sandwiches and mini desserts! I went a few years ago.

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The American Museum of Natural History

You’ve all seen “Night at the Museum,” right? Well this is where it was filmed Travel around the world and back in time through this immense museum, located on the Upper West Side along Central Park.


The Met Cloisters

This branch of The Met is located at the northern tip of Manhattan. It’s an incredible old building on the edge of the Hudson River and Fort Tryon Park. Once you hop off the subway it’s a beautiful walk through the park, although be prepared for steps! This museum is filled with Medieval art, and it currently also hosts many mannequins from the Heavenly Bodies exhibit as well.


Day 5: Brooklyn & The East Side

On the last day in the city it’s time to hit anything on your list that you haven’t done yet. I recommend a more relaxing day so you can end the night with energy for a Broadway show. This is something everyone must do while they’re in New York!

Brooklyn Botanical Gardens

Start your day by popping over to Brooklyn to explore these gorgeous gardens. I personally love botanical gardens, and they’re always a great Instagram spot. Plus, every Friday before noon it’s free admission!


The Met Breuer

The final location of the Met is on the East Side and it houses modern and contemporary art from the 20th and 21st centuries. Make good use of your 3-day passes and spend some time here browsing through the galleries.


Central Park

Grab some lunch and enjoy it in Central Park. There is so much to do here from sitting and enjoying views of the skyline surrounding you, to walking through the miles of trails, visiting the Central Park Zoo or renting paddle boats. I love walking through and seeing the different statues like Alice in Wonderland and the Egyptian Obelisk.


Enjoy a Fancy Dinner

One of my favorite things I did was eat dinner at the base of the Empire State Building. Tacombi is an incredible Mexican Restaurant with several locations across the city. It’s very aesthetic and the food is incredible. The tacos were seasoned to perfection and my Mezcal Mule was delicious! You should treat yourself to a nice dinner of any kind of food on your last evening in Manhattan.


A Broadway Show

Something everyone must do at some point in their life is see a show on Broadway in New York. I’ve seen three in my life: Cinderella, Les Miserables & Phantom of the Opera. Each show was absolutely spectacular! There is no better way to end your trip than by enjoying an evening at the theater.


An End Note:

This is a packed and fun NYC itinerary! However, there is so much to do here that I haven’t even touched on yet. I hope these recommendations help plan your next trip to the city. Other things I love in New York are the Bronx Zoo & River Walk, Washington Square Park, the East Village, SoHo, the Museum of Modern Art, the Tenement Museum, and exploring more of the other boroughs like Brooklyn and Queens.

What are some of your favorite things to do in New York that I haven’t touched on?

4 thoughts on “Your 5 Day Itinerary in New York City

  1. mphadventuregirl says:

    I been to NYC- special trip with my mom at age 12 in 2006. I went to American Girl, Central Park, Wicked, Natural History Museum, and more. Don’t remember much. All I remember about Wicked is being with mom and that “Popular” was my favorite song: but the impact shows. You just can’t leave NYC without a broadway show.

    Next time I go to NYC whenever that is, I want to plan it around theatre. One show go to the Metropolitan Opera. Other shows will be Broadway shows. Have at least one preplanned. Then the others just pick the day of. Just theatre-themed. I am a musical theatre fanatic who has only seen one show one show on Broadway: just don’t live close enough: good thing tours exist.


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