New York Itinerary : 4 days in NYC

New York, this heaving, gritty, passionate, buzzing and oft captivating city is a place you will likely want to return to over and over. From the bright lights of Times Square, to the serenity of Central Park, it is a city of many sides. This New York itinerary for 4 days will explore some must dos on your first visit, alongside options for those who might have less or more time to explore.

Use the table of contents to skip to the desired section if you’re in a hurry…

Orientation & Transport

The easiest way around New York is by Subway. The metro has an extensive network of lines that run throughout Manhattan and over to Brooklyn and Queens. You can buy single-use tickets for $3; or a more cost-effective way is to buy a 7-day pass for $33. PATH, AirTrain, and Express buses will deduct from the value on your card, so add extra to this reusable pass to use these services.

Another method is to get your walking shoes on and explore Manhattan on foot. But don’t be fooled, the north to south blocks are much shorter than the east to west city blocks. I suggest walking in the mornings and taking either the subway or a yellow cab once you run out of steam.

Manhattan is laid out in a grid pattern, with avenues running north to south and streets running east to west. 1st Avenue is on the East River side, 11th Avenue on the Hudson River side. 1st Street is down in the Bowery, and 193rd Street us up in Fort George. If you plan to hit all the attractions on this list, you might consider purchasing a New York CityPass.

Lodging in New York

I enjoy being in the thick of things, so would recommend lodging in New York between Central Park and Midtown, between 3rd and 9th. This square of Manhattan has many attractions within it, and is a great walkable area. At the lower end of the budget (this is relative, as this is Manhattan, and not much is cheap cheap), try Pod 51 hotel (230 E 52st St) – the modern but basic rooms are a good compromise for location.

A very central and stylish mid-upper range option is the citizenM Times Square. While the rooms are not huge, technology is great + they have an amazing guest-only rooftop bar. If you’re looking for old-time New York luxury with Central Park views, you cannot beat The Pierre – a Taj Hotel (2 E 61st) or the deco Carlyle off Madison Ave.

4 Days in New York : Itinerary

Day 1: The High Line + Greenwich Village + Whitney Museum and/or River Cruise

Walk the High Line

The High Line is a long urban walking trail built on an abandoned raised train line. Running between 30th Street in Midtown to Gansevoort Street in the Meatpacking District, it is one of the best ways to orientate yourself and see the city from above. As you walk along this elevated garden route you’ll get to see the city from a different perspective, enjoy sculptures, seating and amazing views.

Near the south end of the High Line is the Chelsea Market – this exceptional food hall is home to world class food shops, a fishmonger, delicatessens and more.

Greenwich Village

Greenwich Village is one of the most well-known neighbourhoods in New York. Once famous for being an artist’s enclave, this has left its bohemian mark on the place. Explore the boutique shops, art galleries and eateries.

There are so many lunch options, you’ll not have difficulty finding a spot in any budget. My picks are:

• Joseph Leonard – A tiny cute bric-a-brac kinda place, serving American classics. No reservations, you’ll probably have to queue.
• Boucherie West Village – A french bistro. If you like absinthe as much as I do, these guys had a good selection behind the bar.
• Spicy Moon Vegan Szechuan – looking for some delicious vegan food, this place has plant based adaptations in a modest setting.
• Dominique Ansel Bakery (soho) – If you’re having fun playing food bingo while you’re in New York, then a ‘cronut’ (croissant / donut) is probably on your list. Dominique Ansel, creator of this oddity, has a shop in nearby Soho.

Sightseeing in Greenwich Village

Sights of note in Greenwich village include the Stonewall Inn , a gay bar that was the centre of the Stonewall Riots, and the beginning of the gay rights movement. It is now a national historic monument.

For any fans of the TV show Friends, the apartment block used as the exterior of the show is located in Greenwich Village (90 Bedford Street). There are food tours, and even ghost tours around Greenwich Village!

Hudson River Cruise and / or Statue of Liberty

There are many ways you can see or experience the Statue of Liberty. You can take a river and harbour cruise that circles the statue, as well as offering great views of the New York skyline. Or you can take a tour of the Statue of Liberty itself and add on Ellis Island too. If you have time, these two sights are a worthwhile way to spend a day in New York.

The other way to see the Statue of Liberty (for free) is by taking a trip on the Staten Island Ferry. This free ferry runs between the Whitehall Terminal (near Battery Park) to Staten Island, and right by Lady Liberty. While you don’t get to stop off and tour the statue by this route, it’s a good option if you are on a budget / short on time.

Have dinner at Fraunces Tavern (54 Pearl St) – this historic tavern has a museum, lots of revolutionary relics, and delicious food.

I recommend the giant pretzel!

Day 2: 9/11 Memorial + One World Trade Center + Brooklyn Bridge

Breakfast at a diner

Start your day with breakfast at a traditional diner. Some of my favourites are the Times Square Diner (807 8th Ave), Square Diner (33 Leonard St), or Pearl’s Diner (212 Pearl St). These diners / luncheonettes are famous for their generous portions, long hours, and all-day breakfast options. A stack of American style pancakes, or eggs any style and bacon… or all of the above. You won’t leave hungry.

9/11 Memorial

No visit to New York is complete without paying your respects at the 9/11 Memorial. The two pools go deep into the former foundations of the twin towers, eternal waterfalls that invite you to reflect and remember. The names of every person who passed written on the edging of the pools. It is such a moving place, and you will be pressed not to be brought to tears by visiting.

Note: We noted a few people taking selfies and larking around at the memorial – which I found really disrespectful. When visiting memorials it’s important to remain considerate.

The 9/11 Memorial Museum sensitively displays items from the building, personal items that tell the stories of those who died, and exhibitions that explore how rescues occurred. It is a huge museum, so will take many hours to see it all.

One World Trade Center

The new One World Trade Center or ‘Freedom Tower’ opened in 2014. It is the tallest building in the USA, and in the Western Hemisphere. The observation floors at the One World Trade Center are on the 100, 101 and 102nd floors of the building, and offer amazing 360 degree views out floor-to-ceiling windows.

OWTC is so tall that during bad weather the top of it disappears!

Brooklyn Bridge

It’s time to get your exercise with a jaunt over the Brooklyn Bridge. This 2.2 mile / 3.6 km round trip will take you over the beautiful 1883 suspension bridge. Pedestrian access is via a walkway above the car lanes, this offers great views of Brooklyn and back towards Manhattan.

Fun Fact – The construction of the Brooklyn Bridge was mostly overlooked by a woman (unusual in the late 1800s), after Emily Warren Roebling‘s husband, the chief engineer, became bedridden with illness. Emily served as the conduit between her husband and the project, but ended up pretty much running the show – learning the engineering skills and managing the project. She finished the build before the deadline and was the first one to cross the bridge in a carriage!

Have dinner in Brooklyn! For something special, The River Café offers fine dining overlooking the river. Or for a cheaper option, Juliana’s Pizzeria is highly rated. Visit the nearby Granite Prospect Scenic View for a dusk or night time view of the New York Skyline.

If you have time, grab a cab and explore Williamsburg – great hipster bars and nightlife.

Day 3: Breakfast at Tiffany’s + Biking in Central Park + NYC Architecture + Times Square by night

Breakfast at Tiffany’s

The movie Breakfast at Tiffany’s brought the style and grace of this flagship jewellery store to the big screen. Audrey Hepburn in that iconic Givenchy dress, standing in front of the store windows, eating her pastry and coffee – it’s an endlessly memorable scene. Grab yourself an early morning coffee and your walkable breakfast food of choice and have your Audrey moment!

Biking in Central Park

Central Park is one of the most recognisable places in the world (and one of the most iconic filming locations in the USA), and biking around it is an absolute joy! There are bike hire places nearby the park, keep an eye on Groupon and other voucher sites for deals on bike hire – we got 2 x bikes for 2 hours for only $15. 2 hours is definitely the minimum you will need – I would suggest 4 hours is a better length of time. Don’t forget to rent a bike lock so that you can secure your bike if needed.

The roadways within Central Park have bike lanes, and also attract those wanting to actually exercise (not just ramblers and meandering sightseers), so watch for the etiquette and stay to the side if you are not a confident rider.

Some great stops within Central Park: Gapstow Bridge, the Balto Statue, the Loeb Boathouse, Bethesda Fountain (pictured), Strawberry Fields (John Lennon Memorial); and you can also see the nearby Dakota building where John Lennon once lived (and Yoko still does).

Visit some famous architecture

The architecture in New York is some of the most historically important, interesting, dynamic, and famous in the world. The city was the vanguard for high-rises and innovative space designs due to the limited footprint available on Manhattan island.

You can explore yourself, or take an architecture walking tour. Many of the iconic buildings can be seen along or just off 5th Avenue between 50th Street and 23rd Street. Start at the St Patrick’s Cathedral on the corner of 50th and 5th; then to the Rockefeller Center (pop up to the Top of the Rock for amazing views); take a detour to Grand Central Station (89 E 42nd St) and the Chrysler Building (405 Lexington); then back to 5th Ave to see the grand New York Public Library (476 5th Ave); and further down 5th to the Empire State Building (20 W 34th St); and 1 more mile down to the Flatiron building (175 5th Ave).

This 2 mile / 3 km route offers a lot of bang for your buck architecture-wise.

Have dinner on Restaurant Row (46th Street between 8th & 9th Ave). You can get any kind of cuisine, but my favourite spot is the Hourglass Tavern.

Times Square at night

If you’ve picked a hotel near Times Square you have most likely already seen the bright lights and crazy huge billboards in the area. There is raised seating, buskers, and plenty of things to do in the area. Why not take in a Broadway show like The Lion King, or visit a rooftop bar or prohibition-style bar like Lillie’s Victorian. In the city that never sleeps, embrace the nightlife if you can!

Day 4: The Met or Coney Island + Tenement Museum + Katz’s Deli

Options for your morning: The Metropolitan Museum OR Coney Island

If you had more time I would suggest doing both of these things, but if you only have 4 days you’ll probably have to pick and choose.

The Met

The Met is an incredible museum, and is my top museum pick if you only have a layover in New York. With over 5000 years of art from around the world, it is a place you can get lost in for many hours. Don’t forget to visit The Met Roof Garden Bar for views out over Central Park.

Coney Island

There are so many fun things to do at Coney Island, for both kids and adults alike. Coney Island is a bit of a kitsch nostalgia trip, and perfect for those who enjoy fringe culture. Enjoy the amusements, visit a circus sideshow, or take a walk along the Riegelmann Boardwalk for some fairground-style food. Don’t forget to eat a famous Nathan’s hotdog!

55 minutes on the Q or B train will get you to Coney Island, so it is a time investment, but it’s an interesting ride out into the Long Island neighbourhoods.

Tenement Museum

The Lower East Side has a fascinating history of immigration, crowds of cultures colliding in sometimes difficult and sometimes amazing ways. The Tenement Museum encompasses two tenement buildings on Orchard Street; and offers a glimpse of life in this highly populated area. You can also learn more about the immigrant experience in New York by taking one of their neighbourhood walking tours.

Katz’s Deli + Lower East Side Entertainment

The Lower East Side offers a smorgasbord of eating and entertainment options. One of the most iconic, made famous by the movie When Harry Met Sally, is Katz’s Delicatessen (205 E Houston St). When you enter you will get a token and proceed to one of the many pastrami cutters who are preparing the meat for your sandwich (don’t forget, tip your cutter!). You will then move on to the accoutrements, add a drink of choice and find a seat. If you’re lucky, you can sit at the same table as Meg Ryan and Billy Crystal.

You will only need one sandwich between two unless you’ve got a huge appetite. These are epic and very generous. You will be asked to return the token when you leave, so don’t lose it. Be sure to pick up some Katz’s Deli merchandise on your way out – I mean, who can resist a “Send a Salami To Our Boys in the Army” T-shirt? 😉

Enjoy the bars and nightlife around Orchard Street, such as The Slipper Room;

and be sure to grab yourself some dollar slice pizza on the way home!

Love this US city guide? Then check out my 20 best USA city breaks article!

All photos & content © Hannah Henderson and may not be used without permission (sharing this blog post is fine, though!). Images shot with a Canon DSLR T3i Rebel + Canon EF-S 18-135mm f/3.5-5.6 IS STM; and an iPhone.