This is What You Should Do With 5 Days in New York City
New York City is truly the city that doesn’t sleep. There are so many areas to explore, restaurants to try, bars to visit for a view and a drink, and more. There are, of course, so many popular tourist things to do in New York but this is my list of the things you should actually do when you go to NYC.
Day 1 – Central Park and Midtown
I typically like to do the most tourist items on my first day in a city, almost as a way to check off the list the key places I know that I need to go. This leaves the rest of the trip to have more flexibility in spending more/less time where I like and do more wandering exploring without feeling like I need to make sure I still get X,Y, and Z done.
Central Park
Central Park, spanning 51 blocks, has so much to offer. I recommend coming earlier in the day and grabbing breakfast at one of the cafe’s in the park itself. My favorite isLe Pain Quotidien. If the boathouse is open (April through November), I also recommend boating on the lake which offers picturesque views of the skyline from the water. The boats fit up to 4 people and are fairly easy to row. It costs $15 for an hour including the life vests.
I recommend exiting on the Southeast end of the park to end up on 5th Avenue.
5th Avenue, Rockefeller Center, and radio city music hall
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5th Avenue is one of the best shopping streets in New York. This is where you’ll find your classic designers, top hotels, and of course, the Saks 5th Avenue storefront. Whether buying or window shopping, it’s a must to walk down and see some of the window displays here as you walk towards Rockefeller Center.
Rockefeller Center has select shops outside and also an underground with hundreds of stores and restaurants. I recommend spending a bit of time around here as the iconic area is super lively and has some great speciality shops. I also recommend walking a block down to see Radio City Music Hall.
Grab Coffee at Maman
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Maman is a New York City coffee shop chain which features a very cute aesthetic inside full of wood and trees along with incredible coffees and pastries. There are many throughout the city but there is one a couple blocks from Rockefeller.
Empire State Building
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Empire State Building is 0.8 miles from Rockefeller Center. You’ll be able to enter the lobby but won’t be able to move through the building as its locked down by high security. You can buy tickets to go to the 86th and 102nd floors for the observatories but I personally recommend getting viewpoint tickets from the Edge or On The Edge instead which I’ll go into more in below (that way you can see the skyline with Empire State in it!)
Catch a Subway at Grand Central Terminal
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Grand Central is one of the most stunning buildings, with the classic ticket booths and a 1944 celestial mural on the ceiling. There are also shops and restaurants in Grand Central if you want to walk around for a bit. This can honestly be a quick stop but very memorable as the classic station feels like you are on a Harry Potter set.
get tickets to a Broadway Show
There are incredible shows to pick from on Broadway, which are some of the best productions in the world. From the theaters to the costumes to the actors, the shows are spectacular. My personal favorites have been Lion King and Hamilton but explore which show sounds most entertaining to you!
For cheap last minute tickets, go to the TKTS Booth in Times Square. You can get tickets for often a 50% discount.
Times Square
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If you have spoken to anyone who visits New York, the first thing they will tell you is that Times Square is awful. And I agree. However, I think it is worth seeing if you’ve never been to NYC before but all you’ll need here is approximately 10 minutes. My recommendation is to go at night to see the lights pop best. If you can, avoid going into the tourist-trap restaurants and stores here.
Day 2 – West Village and Chelsea
Walk Through West Village
West Village has your classic brick buildings with fire escapes everywhere, lined with shops and restaurants on the street front. This is one of the best spots, and most expensive, in NYC for shopping and dining. I recommend walking down Bleeker Street to go into many of the shops including boutiques and favorites like Aesop and DÔEN.
One block away from Bleeker street is Greenwhich street which is a similar vibe, but instead lined with all restaurants and bars.
Get brunch or happy hour on Greenwhich street
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This street has some of the most vibey restaurants in Manhattan, with some of my favorites being Dante and Rosemary. I recommend walking down and seeing which ones catch your eye to grab a meal!
Walk Through Chelsea Market
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Chelsea Market is one of my favorite parts of New York, with 35+ shops and restaurants inside. I personally recommend grabbing a donut at the Doughnuttery.
Visit one of largest Starbucks Reserves
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At, 23,000 sq. feet, this Starbucks Roastery is one of the biggest in the world and located right next to Chelsea Market. You’ll find a full bar on the 2nd floor, offering espresso martini flights, and multiple barista counters on the 1st floor with coffee options from around the world. It is truly an experience if you like Starbucks to pop in and check-out. Their official page shares more about the Roaster’s design and menus.
Walk the High Line
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You can hop on the high line by taking the elevator or stairs at W. 16th Street and 10th Avenue, right behind Chelsea Market. You’ll walk between apartments above the streets of New York in a path that uniquely mixes industrial and nature. The path will end at Hudson Yards which is the next place you should absolutely spend a little time.
Stop at Hudson Yards
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Hudson Yards features both The Vessel and the Hudson Yards indoor mall. Unfortunately, the Vessel no longer allows patrons to go up the building but it is still very cool to see from the ground. I also recommend popping into the mall which is arguably the nicest in NYC. If going around Christmas time, this is one of my favorite festive areas in the city! The mall decks every square inch with warm Christmas lights. Learn more about this in my article on NYC for Christmas.
Day 3 – Wall Street, 9/11 Memorial, and SoHo
walk through wall street
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Wall Street is one of the most iconic spots in New York, known all around the world. I recommend walking through the area, visiting the famous bull, and then spending some time by the 9/11 memorial. There is a 9/11 museum here as well which I haven’t been to myself but it has amazing reviews. Across the street, is the Oculus mall which was built to resemble a dove.
Close by to Wall Street is also Tribeca which has some amazing restaurants to try. If you’re hungry while down here, I recommend walking the few blocks to this neighborhood to try either Bubby’s or Tamarind Tribeca which are two high-rated spots.
Go Shopping in SoHo
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SoHo is arguably the best shopping district in Manhattan (and maybe in the US?). You’ll find yourself wandering through blocks of every store you can think of including both big name brands and designer brands.
I recommend stopping by Ladurée for some tea time or for a quick bite if you have some extra time! The outdoor garden there is stunning and the pastries are delicious!
walk through Washington Square Park
Washington Square Park connects the West Village to SoHo and is lively at any time in the day. You’ll see the Washington Arc, chess tables where people usually play, many enjoying time with friends, and usually a few popups.
Get Tickets to a Show at The Comedy Cellar
This is the most famous comedy club in NYC where all famous comedians both kick off their careers and return to perform. It’s required to make a reservation at any of the three locations in advance and I recommend getting there early as the lines to enter will be crazy. Note that you will not know who will be performing before you arrive, your phone will be taken and sealed from you during the duration of the show, and there will be a 2 drink minimum per person.
Some of the big comedians who have performed here are: Louis C.K., Dave Chappelle, Amy Schumer, Ali Wong, and Kevin Hart.
Grab Drinks at a Speakeasy, Rooftop, or Piano Bar
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There are so many vibey bars in NYC that make a night out a must-do on your trip. My favorites have been PHD Terrace Rooftop, Please Don’t Tell Speakeasy, and The Nines Piano Bar.
Day 4 – Upper East Side
Get Coffee at the Ralph Lauren Cafe
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One of the gems on the Upper East Side is the Ralph Lauren cafe. Located directly across from the Ralph Lauren store, this upscale coffee shop is such a posh coffee experience. I got the seasonal latte (gingerbread) which was phenomenal and their ham & cheese baguette. The portions are very small for the price but it is worth experiencing for the upscale vibe and uniqueness.
Have a Museum Day at The Met
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The Met is four floors and 2.2 million square feet so it’s safe to say you could spend an entire day here; with everything inside from beautiful architecture to art/artifacts from all over the world. This is also where the iconic Met Gala takes place each year so if you aren’t a big museum fan, it is cool to even see from the outside.
Visit their official website for more information on all the exhibits. Note that many corporations will also give you free access to the Met so check with your company to see if it is one of them!
Watch the Sunset from One of the Top Viewpoints
Manhattan’s entire skyline is skyscrapers so it’s safe to say there are a lot of different viewpoints for the city, whether it’s a famous landmark like Empire State or a floating ledge like The Edge or simply a hotel bar/restaurant rooftop. These are the top viewpoints I recommend picking from (you only really need to do one):
- The Edge (pictured above) – the edge is the “highest skydeck in the Western hemisphere” that sits 1,100 feet above ground. The iconic part of this viewpoint is that the floor is glass so you will be looking at NYC streets below your feet.
- SUMMIT One Vanderbilt – an immersive experience with views and reflections to play on your senses and feel like you’re in a different dimension.
- Top of the Rock – this is the viewpoint from the top of Rockefeller Center. It is the most touristy of the three but offers amazing views and is very centrally located.
Although usually slightly more expensive, I recommend booking tickets early for the sunset hour. This lets you see the view during the day, watch the sunset, and see the night skyline which are both very different views/experiences!
Day 5 – A Day in Brooklyn
Walk The Brooklyn Bridge
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Walking the Brooklyn Bridge is one of the most iconic activities in NYC, with 16,000 vehicles, 30,000 pedestrians and 3,000 people crossing it every day. The walk is 1.6 miles across and takes on average about 30-40 minutes each way. It’s a great way to get across into Brooklyn for the day and then you can take the subway back to Manhattan.
Visit Dumbo and timeout Market
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Dumbo is the most visited part of Brooklyn as there is Brooklyn Bridge park, Timeout Market, and The Brooklyn Flea Market. I recommend grabbing lunch at Timeout market from one of the 21 food “concepts” here.
Williamsburg
For a day in Brooklyn, Williamsburg should definitely be on your list. This very trendy neighborhood has lots of great shopping on Bedford Avenue with stores like Muji, On Running, and various local vintage shops. There is also a rooftop house show at the Williamsburg Hotel every Sunday (if the weather permits) that offers amazing views of Manhattan skyline if you’re looking for an event or live music.
honorable mentions:
- Natural Museum of History
- Bryant Square Park
- Eat New York City Bagels, Pizza, and Cheesecake
- Little Italy
- The Little Island
- Statue of Liberty