How to Spend Five Days in New York City

New York City has an array of fun things to do and amazing things for you to see
New York City has an array of fun things to do and amazing things for you to see | © Jon Arnold Images Ltd / Alamy
Rachelle Eason

A five-day New York City break goes by quickly. With so much to do and see, it’s hard not to feel like no matter how much you accomplish, you’re still missing out on a world-class restaurant or a top-notch event. Culture Trip brings you a tailored itinerary to make the most of five days in New York City.


Fabiane's Café and Pastry Shop

Cafe, Bistro, Pastelaria, American

Strawberry French Toast with bacon and eggs
© John Kelly / Alamy
Fabiane’s is a little piece of France in the heart of Williamsburg. Choose from their many breakfast and brunch options; if you’re in the mood for something sweet to start off your day, go for the French toast with strawberries or the waffles. If you’re more of a savory breakfast type, try the organic eggs with smoked salmon, scallions, and potatoes. Almost every item on their menu has a gluten-free counterpart, so there’s something for everyone at this charming Brooklyn-based eatery.

Shopping in SoHo

Archaeological site

The very busy Broadway with Prince Street in Soho, New York City
© agefotostock / Alamy
Your five-day NYC break should definitely include heading on over to Manhattan for some quality shopping in one of the city’s most fashionable neighborhoods. SoHo has a surprisingly rich history, with many of its stunning buildings dating back hundreds of years, but it was also something of an unofficial artist colony back in the 1960s and was home to some of the most diverse and creative figures associated with NYC. Are you a film buff? You may recognize this neighborhood from major Hollywood blockbusters such as Hitch, Ghost, and Spiderman. As you stroll down SoHo’s charming cobblestone streets, be on the lookout for historical plaques or celebrity sightings.

The Picnic Basket

Restaurant, American

A delicious sandwich sat on a piece of paper on top of a wooden surface at The Picnic Basket
Courtesy of The Picnic Basket

For lunch, head to the Picnic Basket for memorable and delicious sandwiches. We highly recommend the French goat cheese sandwich with sundried tomato pesto, grilled zucchini, figs, tomatoes, and fresh greens if you’re in the market for something cold. Alternatively, you can opt for a hot-pressed sandwich such as the prosciutto di parma with mozzarella and sun-dried tomatoes or the turkey and herb sandwich with Swiss cheese and basil pesto.

Brooklyn Bridge Park

Bridge, Gym, Park

The Brooklyn Bridge connecting Manhattan and Brooklyn in New York on a sunny day, with grass underneath the bridge
© Peter Horree / Alamy Stock Photo
It doesn’t matter which pier you venture out to in Brooklyn — the views of Manhattan will always be breathtaking. That being said, Pier 1 offers a one of the best views, and you can enjoy both the Manhattan skyline and the Brooklyn Bridge. Weather permitting, sit outside and take in your surroundings, explore neighboring piers to play beach volleyball, or visit the historic Jane’s Carousel in Brooklyn Bridge Park.

Sweet Chick

Restaurant, American

An outdoor view of Sweet Chick, with a rustic sign above the restaurant and bikes and people outside the building
© Robert K. Chin - Storefronts / Alamy
Breakfast for dinner? Yes please! Sweet Chick is Williamsburg’s go-to for chicken and waffles, and it is unsurprisingly popular amongst locals. If you’re going to eat here, we highly recommend going all out. Start off with the mac and cheese appetizer (a gooey mix of three cheeses topped with a Ritz cracker crunch) and then move on to the bacon-cheddar chicken and waffles.

The Knitting Factory

Music Venue

An exterior view of the Knitting Factory Brooklyn, with a black cover with white writing and people standing outside
© Robert K. Chin - Storefronts / Alamy
The Knitting Factory is a great way to close out the night. Don’t let the name fool you — the Knitting Factory hosts great concerts featuring talented up-and-coming artists. This space hosts some sort of performance every night, so check their website beforehand to ensure that there’s still space. If you’re not a concert person, check out their comedy nights instead. You can buy tickets for most of these events at the door, but we suggest buying them beforehand online.


Tom's Restaurant

Diner, Restaurant, American

An exterior view of Toms Restaurant, with blue parasols, red chairs and a blue and red sign
© Wojciech Migda / Alamy Stock Photo
If you’ve ever watched an episode of Seinfeld or listened to Suzanne Vega’s 1980 hit ‘Tom’s Diner,’ you’re probably somewhat familiar with Tom’s Restaurant. A staple of the Upper West Side, Tom’s Restaurant has been around for almost 80 years. History lesson aside, their food is tasty, and more importantly, they serve breakfast all day (so it’s perfect for late risers). Opt for the pancakes or the French toast, or if you’re in the mood for something savory, try their bacon, egg, and cheese sandwich.

Central Park


A skyline of Central Park South in New York City, with many green trees, grass and pathways with a city backdrop
© Sean Pavone / Alamy
Time to burn off all that breakfast. Central Park is an absolute must-see when visiting New York, and while you certainly won’t be able to see it in its entirety in one afternoon, you can certainly catch some major points of interest. Rent a row boat by the Bethesda Fountain, explore ‘The Pool’ up by 100th street, or simply stroll and relax under some trees.

The Bronx Zoo


Two brown Grizzly Bears standing on a rock at Bronx Zoo, New York, with trees in the background
© Edward Westmacott / Alamy
For such a metropolitan area, New York City has a lot of zoos. You can stop off at the smaller-but-still-impressive Central Park Zoo while you’re there, but arguably the most famous and expansive zoo in New York City is the Bronx Zoo. General admission is free on Wednesdays, so aim for a mid-week visit, but either way, it’s worth the trip.


Greengrocer, Market, Restaurant, Grocery Store, Bar, Charcuterie, Butcher, Fishmonger, Cheesemonger, Italian

People shopping for food and being served beside a counter at Eataly New York
© Peter Horree / Alamy

For some of the greatest panini in the city, head over to Eataly. The bread is always fresh and is made in their in-store bakery, and you will be hard pressed to find a better variety of toppings. Not in the mood for a hot or cold sandwich? Explore the vast expanse that is Eataly for some savory meals. There are several restaurants throughout the store, so be sure to check out every last one.

Nitehawk Cinema

Cinema, Theater, Movie Theater

An outside view of the Nitehawk Cinema in Brooklyn, with an illuminated sign
© Sipa US / Alamy
There’s no need to head out for dinner if you wish to end your evening with a visit to Nitehawk Cinema. This Brooklyn-based venue takes the ‘dinner and a movie’ concept to a whole new level, offering a menu that pairs with the film that’s playing. Nitehawk shows a great mix of recent and retro films, and if you don’t like the movie-themed menu when you visit, they offer other food options including steak sandwiches and crispy fish tacos.


Tompkins Square Bagels

Cafe, Pastelaria, Bakery, Dessert Shop, American

You can’t fully experience NYC without its star attraction — the bagel. Although the multitude of choices may seem overwhelming, you should stop by Tompkins Square Bagels for a particularly fantastic bagel. With over a dozen cream cheeses to choose from, your bagel won’t be anything other than delicious. Try the bacon herb cream cheese on a poppy seed bagel, or go for fruit butter on a French toast bagel.

Stroll the Coney Island Boardwalk


A fun fair with a big colourful wheel, colourful balloons and people walking around at Coney Island, Brooklyn, New York City
© robertharding / Alamy
This Brooklyn icon has been around for over a century and is home to one of the largest amusement parks in the United States. After Hurricane Sandy, Coney Island suffered some heavy damage, but has since returned to its former splendor. It can be a bit of a trek depending where you’re staying in the city, but it’s worth it for a ride on the famous Cyclone and for a peek into old-world New York life.

Museum of the American Gangster


Carrying on with the theme of old-world New York, head back to Manhattan and learn about the fascinating role of the American gangster in history. The Museum of the American Gangster consists of two rooms filled with great artifacts and is located just above a speakeasy. The street on which it’s located was once frequented by the likes of Al Capone, Lucky Luciano, and John Gotti.

Burger and Lobster

Restaurant, American

A delicious-looking bun with lobster placed inside, in a paper container at Burger and Lobster
Courtesy of Burger and Lobster
After wandering around the nearby Chelsea and Meatpacking District neighborhoods, head to Burger and Lobster for a uniquely indulgent meal. For $20 you can get a lobster roll, or, if seafood isn’t your thing, try a burger. Burger and Lobster has forgone the traditional menu option for an easier tactic — spend less time choosing and more time eating and having fun with your dinner companions. Each dish comes with a side salad and fries, so you’re sure to leave fully satisfied.


Locanda Verde

Restaurant, Italian

A delicious sandwich being split in half over a wooden surface at Locanda Verde
Courtesy of Locanda Verde
Locanda Verde is a popular spot amongst locals. The decor is rustic Italian with an open kitchen plan, allowing customers to watch their food as it’s prepared. The breakfast crowd is quieter, but the lull between the breakfast and lunch rush is a prime time to grab a quick bite. The sheep’s milk ricotta with burnt orange and truffle honey on toast is a favorite amongst patrons, but if you’d like something slightly more traditional, we recommend the hazelnut-crusted French toast.

Guggenheim Museum, New York

Building, Museum

A view looking down at the white and modern decor at Guggenheim Museum, New York
One of the most prized art institutions in the city and an unmissable part of any New York break, the Guggenheim is one of many necessary stops on the Upper East Side’s Museum Mile. Aside from the unparalleled exhibitions, the building itself, designed by famed American architect Frank Lloyd Wright, is a sight to see.

Catch a Broadway show


Colourful Broadway show signs along 42nd Street at Times Square, New York City, with a yellow taxi outside
© Brian Jannsen / Alamy

You can’t go to New York without seeing a Broadway show, and the range of shows will appeal to even the most cynical theatre-goers. Expect mesmerizing backdrops, catchy tunes, and stellar casts. Every theater is full of its own history and usually runs specific shows, so be sure to check them out on the Broadway website. Although dressing up is optional, we recommend that you make this a night on the town.


The Greek

Gastropub, Restaurant, Dessert Shop, Greek

NYC is a hub for eclectic culture and cuisine, so as long as you’re here, try something a little different. The Greek is a Greek tavern and gastropub with a rustic Mediterranean feel. Start off with the spread, which comes with a crispy, lightly-toasted bread, and then move on to the kota(a baked chicken with herbs and kefalograviera cheese). As for dessert, you can never go wrong with the sokolatopita. While The Greek is on the pricier side, this is one splurge that will leave you more than satisfied.

Pier 25 Mini Golf

Park, Sports Center

There’s no better way to end your New York City excursion than by channeling your inner child. Grab some friends for a round of mini golf at Pier 25. This 18-hole miniature golf course has it all; a waterfall, a pond, little bridges, and sand traps. The one thing it holds over all other course is that it overlooks the Hudson River, which is a seriously breathtaking view. This is a pretty cheap way to have fun, as adult tickets are only $5, and the course opens for the season on April 18th, 2016.

See the best places to stay in New York with rooftop views. Active travelers should check out our guide to the best bike paths in NYC.

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