5 days in New York, an itinerary for first time visitors

DUMBO Brooklyn - Five day New York itinerary
DUMBO Brooklyn

New York City, the city that never sleeps. The most famous city in the world, seen in movies, TV shows, books, and more, New York draws in millions of tourists each year from almost every country in the world. They come to shop, to eat, to experience a Broadway show, to walk the streets of Little Italy, Soho, Chelsea, and TriBeCa, to marvel at the architecture, the underground, and the skyline.

New York asks for “your tired, your poor, your huddled masses yearning to breathe free”, remembers the World Trade Towers, goes gaga for Fashion Week, the US Open, and the Macy’s Thanksgiving Day Parade.

New York City has five boroughs: Manhattan, Brooklyn, Queens, the Bronx, and Staten Island. Most visitors stay on Manhattan and visit Brooklyn, and maybe Queens, but few ventures to Staten Island or the Bronx unless visiting something specific.

Manhattan is nominally divided into Uptown, Midtown, and Downtown, all of which are subdivided into more than 50 neighborhoods, like the Upper East Side, Hells Kitchen, Chinatown, Chelsea, Greenwich Village, Harlem, TriBeCa, or NoLiTa. No matter what you want to do in NYC, you’ll find it in one of the many exciting neighborhoods.

But what do you do in New York? My five-day itinerary for New York City hits the highlights plus a few hidden gems. 

Disclaimer: This post contains affiliate links. This means that should you click on certain links, and then subsequently purchase a product, I will receive a small commission.

Five days in New York

A 5 day New York itinerary for the first-timers

5 days in New York: Day One


Begin your five day New York itinerary with a visit to some of the city’s most famous museums. View ancient art at the Metropolitan Museum of Art (The Met), Van Gogh’s Starry Night at MOMA, or Post-Impressionist art at the Guggenheim. The American Museum of Natural History, featured in Night At The Museum, is home to artifacts, fossils, and information about our collective natural and cultural history and it is one of the top things to do in New York with kids. It’s the largest natural history museum in the world. 

All are located Uptown – The Met, Natural History Museum, and the Guggenheim are all within easy walking distance of each other; the MOMA is on 53rd Street. 

1. Guggenheim Museum

Guggenheim Museum - Five days in New York

  • Cost: Adults $25, children under 12 are free – free with the NY Turbopass.
  • Hours: Daily 10 am to 5:30 pm; open until 8 pm Tuesday and Saturday
  • Website: www.guggenheim.org
  • Getting Here: the closest subway station is 86 Street Station (4, 5, 6)

2. Metropolitan Museum of Art (The Met)

  • Hours: Daily 10 am to 5:30 pm; open until 9 pm Friday and Saturday
  • Cost: Adults $25, children under 12 are free; tickets are valid for 3 days – free with the NY Turbopass.
  • Website: www.metmuseum.org
  • Travel Tip: Purchase your tickets online in advance to skip the line
  • Getting Here: the closest subway station is 86 Street or 77 Street Station (4, 5, 6)
Metropolitan Museum of Art (The Met) - 5 day New York itinerary
view from the roof of the Metropolitan Museum of Art (The Met)

3. MOMA

    • Hours: Daily 10:30 am to 5:30 pm; open until 8 pm on Friday
  • Cost: Adults $25, under 16 years old are free – free with the NY Turbopass.
  • Website: www.moma.org
  • Travel Tip: Admission is free on Friday from 4 to 8 pm 
  • Getting Here: the closest subway station is 5th Ave/53rd St Station (E, M)

4. Museum of Natural History 

Museum of Natural History  - 5 day New York itinerary

  • Hours: Daily 10 am to 5:45 pm, except Thanksgiving and Christmas Days
  • Cost: Adults $23, Children 2-12 $13, Students $18 – free with the NY Turbopass.
  • Website: www.amnh.org
  • Travel Tip: If you pay at the counter, you can “pay what you wish” – all day every day.
  • Getting Here: the closest subway station is the 81st St Museum of Natural History Station (A, B, C)

5. Central Park

Central Park - Five day New York itinerary

After exploring the museums, head for Central Park, one of the most visited urban parks in the world. At over 840 acres, the park is the fifth-largest park in New York. It is bordered by Manhattan and Columbus Circle to the south, Harlem to the north, and the Upper East and West Sides, respectively. While the lakes and wooded areas in the park appear natural, they were in fact landscaped in the 1850s when the park’s governing body commissioned landscape architect Frederick Law Olmsted to design the park.

me in Central Park -Five day New York itinerary

Central Park hosts concerts, memorials, rallies, protests, and more. Visitors come for the zoo, to walk the trails, paddleboat in the lake, skate at the (winter) ice rink, or to relax on the Great Lawn. A visit to Central Park is a must-do while you’re in the city.

  • Hours: Daily from 6 am to 1 am
  • Website: http://www.centralparknyc.org/
  • Getting Here: the A, B, and C lines run along Central Park West and there are multiple stations

You cannot go to New York and not try its famous pizza. Check here where to find the best pizza in New York City

5 days in New York: Day Two 

1. Ellis Island

Ellis Island - Five day New York itinerary
Ellis Island

Take a ferry to Ellis Island and the Statue of Liberty today to learn more about the immigration history of the United States. The complex, officially known as the Statue of Liberty National Monument encompasses Ellis and Liberty Islands and is operated by the National Parks Service. 

Ellis Island 2- Five day New York itinerary
Ellis Island

From 1892 to 1954, Ellis Island was the busiest immigration station in the US, processing approximately 12 million immigrants into the country. Today, visitors can explore the immigration museum or take a guided “Hard Hat Tour” of the south side of the island, which includes the immigrant hospital where immigrants were detained.

me in the Statue of Liberty - Five days in New York

2. Statue of Liberty

Adjacent to Ellis Island is the Statue of Liberty, one of the most recognizable symbols of the United States and a worldwide symbol of freedom. It was designed by Frédéric Auguste Bartholdi, a French sculptor, and gifted to the US by France in 1924. Visitors can climb to the base or the crown of the statue.

  • Cost: $21.50 Adults, $12 children 4 – 12 years for the Crown Reserve Ticket – free with the NY Turbopass.for normal tickets
  • Hours: Ferries depart from 8:30 am to 5 pm
  • Website: Book your tickets in advance on www.statuecruises.com
  • Travel Tip: Tickets sell out very, very quickly, especially for climbing to the crown, so book the minute you know your dates!
  • Getting Here: you have to take a ferry from Battery Park. Get to Battery Park on the N, R, or W lines to Whitehall St Station, or the 1 at South Ferry Station.

Ferries depart from Battery Park, at the tip of Manhattan. Battery Park is named for the 17th-century artillery batteries that line the shoreline, built to protect the settlement behind them. It’s also home to Fort Clinton, the first immigration station in the US, the SeaGlass carousel, and numerous memorials and monuments. 

The entire trip, from Battery Park to the National Park, will take about four hours.

3. Staten Island 

Staten Island  - Five days in New York

Alternatively, if you don’t want to spend money on the above you can take a free ferry to Staten Island to see the Statue of Liberty and the Manhattan skyline.

4. Stock Exchange

Stock Exchange - Five days in New York

Upon return to Battery Park head for Wall Street to see the Stock Exchange. Located at the corner of Broad and Wall Streets, the six-columned facade is quite famous and you never know who you might see. The building is no longer open for tours (post-9/11 happening), but don’t feel too bummed. With the rise in electronic trading, there are less than 1,000 traders on the floor – less than a fifth of what used to be (and way fewer than in movies). To get a glimpse at the inner workings of the financial system, though, you can visit the Federal Reserve, also located on Wall Street. 

You might also like: Off the beaten track things to do in New York.

5. One World Observatory

One World Observatory night view5 days in New York

After leaving Wall Street, head for the One World Observatory, located at the top of the new One World Trade Tower, adjacent to the memorial site at the World Trade Center and having the same name and address as the North Tower. 

The observatory opened on 29 May 2015 and offers 360-degree views of the city.

  • Cost: Tickets start at $34 adults, $28 youth (6 – 12 years) – free with the NY Turbopass.
  • Hours: Daily 9 am to 9 pm; open until 10 pm on holidays and during the summer; opens at 8 am May 1 to September 4
  • Website: https://oneworldobservatory.com/en-US
  • Getting Here: the closest subway stations are WTC Cortlandt St Station (1, N, R, W) or Fulton St Station (4, 6).

5 days in New York: Day Three


Today, spend the day in Midtown, exploring the stretch between 34th and 50th Streets. This area has some of New York City’s most famous landmarks, from the Empire State Building, Rockefeller Centre, Times Square, the New York Public Library, and Grand Central Station. You can do this on your own, or you can take an architectural walking tour.

1. New York Public Library (Stephen A. Schwarzman Building)

New York Public Library - 5 day New York itinerary

  • Cost: free
  • Hours: 10 am-5:45 pm Monday, Thursday, Friday, and Saturday. 10 am-7:45 pm Tuesday and Wednesday, 1-4:45 pm Sundays
  • Website: https://www.nypl.org/
  • Getting Here:  the closest subway station is 5th Ave/Bryant Park (7)

2. Grand Central Terminal

3. Empire State building

Empire State building - Five day New York itinerary

  • Cost: Tickets for the observation deck start at $38; there are a number of packages available
  • Hours: 8am-2am
  • Website: https://www.esbnyc.com/
  • Getting Here: the closest subway station is 33rd St (4, 6)

4. Top of the Rock at Rockefeller Center

Top of the Rock - New York itinerary 5 days

5. Rockefeller Center

Rockefeller Center - 5 days in New York

6. 5th Avenue

5th Avenue is the world’s most expensive street, from the high-end shops to the penthouses that line the buildings on this street. It is also known as Millionaire’s Row or Museum Mile.

  • Cost: free
  • Hours: 24 hours; shops obviously have their own hours
  • Getting Here: 5th Avenue runs along Central Park East. The nearest subway stations are at 60th St and 5th (N, R, W), or the 4 and 6 along Lexington Ave.

7. Times Square

Times Square New York itinerary 5 days

You can’t visit New York without seeing Times Square. Known for its constant signage and the New Years Eve ball drop, Times Square is an icon of the city. 

  • Cost: free
  • Hours: 24 hours a day
  • Website: https://www.timessquarenyc.org/
  • Getting Here: the closest subway stations are the Times Square/42nd St stations on the N, R, W, Q, S, and 7 lines.

me in Times Square- New York itinerary 5 days

Broadway show (cheap same-day tickets at TKTS in Times Square)

A Broadway show is one of the highlights of New York for most people. See a long-running show or snag seats at one of the hottest shows in the city. There are a number of different Broadway theatres, all home to different shows. No matter whether you want a family-friendly show, a lively musical, or a thrilling drama, you will find it on Broadway.

  • Cost: ticket prices vary
  • Website: https://www.broadway.com/ or https://www.tdf.org/nyc/7/tkts-ticket-booths
  • Getting Here: the closest subway stations are the Times Square/42nd St stations on the N, R, W, Q, S, and 7 lines.
  • Travel Tip: The “Play Express” line sells only play tickets (no musicals or shows) and moves quickly. Go early in the day to get the best availability for all shows. Be careful purchasing tickets from someone on the street – illegal tickets are not accepted at theatres.

5 days in New York: Day Four


Head for one of New York’s other boroughs today – Brooklyn. One of New York’s most diverse boroughs, Brooklyn is a hotspot for entrepreneurship, avant-garde art, tech startups, and more. In recent years, the neighborhoods of Brooklyn have seen a dramatic increase in gentrification. Along with higher housing prices and rent, this has introduced designer boutiques, local coffee shops, food markets, and more.

1. DUMBO Brooklyn

DUMBO Brooklyn - 5 day New York itinerary

DUMBO – Down Under the Manhattan Bridge Overpass – is one of New York’s most expensive neighborhoods. While originally this neighborhood, located between the termini of the Manhattan Bridge and the Brooklyn Bridge, It is a hotbed for tech companies, art galleries, boutiques, celebrity chef restaurants, and more. It’s featured in films and TV shows as well as referenced in pop culture a lot.

DUMBO Brooklyn 2- Five day New York itinerary

2. Time Out Market

Time Out Market - New York itinerary 5 days

The Time Out Market in DUMBO is a new dining and culture experience curated by the team at Time Out magazine. It boasts 21 dining venues and 3 bars, as well as event space and art installations. 

  • Cost: free
  • Hours: First floor, 8 am to 10 pm Sunday to Thursday, open until 11 pm on Friday and Saturday. The fifth floor is open from 11 am to 11 pm Sunday to Thursday and until midnight on Friday and Saturday.
  • Website: https://www.timeoutmarket.com/newyork/
  • Getting Here: the closest subway stops are the York Street (F) and the High Street Brooklyn Bridge (A, C)

3. Brooklyn Bridge

After a great meal at the Time Out Market, walk across the Brooklyn Bridge towards Manhattan (in the morning the sun is at your back and you can perfectly see the Manhattan skyline). If you want to do it the other way around, do the below museums in the morning and walk towards Brooklyn in the afternoon.

4. City Hall Park

city hall - Five day New York itinerary

At the Manhattan terminus of the bridge is City Hall Park, a great place for people watching and one of the most vibrant green spaces in downtown Manhattan.

5 day New York itinerary

A few blocks away is the 9/11 Memorial and Museum, a vast plaza and underground museum dedicated to the September 11, 2001 attacks. Because this dark time really defined the early 2000s and the later growth of New York, this is a must-see while you are in the city.

5. 9/11 Memorial Plaza

9/11 Memorial Plaza - 5 day New York itinerary

  • Cost: free
  • Hours: Daily 7:30 am to 9 pm
  • Website: https://www.911memorial.org/
  • Getting Here: the closest subway stops are World Trade Center (1), Cortlandt St (W), and Fulton Street (4, 5) Stations

6. 9/11 Memorial Museum 

9/11 Memorial Museum 5 day New York itinerary

  • Cost: ticket prices start at $26 adults, $15 children – free with the NY Turbopass.
  • Hours: Daily 9 am to 8 pm Sunday to Thursday, open until 9 pm on Friday and Saturday. Last entry is 2 hours prior to closing.
  • Website: https://www.911memorial.org/
  • Getting Here: the closest subway stops are World Trade Center (1), Cortlandt St (W), and Fulton Street (4, 5) Stations
  • Travel Tip: this is a really popular exhibit, so purchase tickets online in advance

5 days in New York: Day Five


Spend day 5 in some of Manhattan’s hippest neighborhoods.

1. High Line

High Line - 5 days in New York city

  • Cost: free
  • Hours: 7am-11pm
  • Website: https://www.thehighline.org/
  • Getting Here: there are 14 access points between 34th and 14th streets; some are handicap accessible while others are not. The nearest subway stations are 14th St (A, C, E) or 34th St/Hudson Yards (7)

2. Chelsea Market

Chelsea Market - Five day New York itinerary

The Chelsea Market is a foodie lovers paradise. There are also some boutique shops inside that are worth exploring.

  • Hours: 7am-11pm, Sundays 8am-10pm
  • Website: http://chelseamarket.com/
  • Getting Here: the closest subway station is 14th St (A, C, E)

3. Washington Square Park

Washington Square Park - New York itinerary 5 days

4. SOHO

soho- 5 days in New York

SoHo, or South of Houston, is known for arty galleries, designer boutiques, quirky bars, and some of the city’s best coffee (and dining, and drinking, and shopping).

5. Chinatown

Chinatown is also a must-see, for its evocative and vibrant atmosphere. Dimly lit dim sum places share sidewalk space with tea parlors and noodle joints. While a riot of color and sound all year long, its at its best at Chinese New Year.

Where to go shopping in New York


New York itinerary 5 days

Shopping in New York is a favorite pastime, and with so many incredible places to shop you really can shop til you drop. Many flagship stores are located in the city, some with notable addresses.

Flagship Stores in New York

Saks 5th Avenue

Victoria Secret Flagship Store

  • Hours: 9am-9:30pm, 10am-9pm on Sundays
  • Website: www.victoriassecret.com
  • Getting Here: 33rd St (N, Q, R, W) or 34th St/Penn Station (1, 2, 3) are the closest subway stops

Macy’s

  • Hours: 10am-10pm, open until 9pm on Sundays
  • Website: https://www.macys.com
  • Getting Here: 33rd St (N, Q, R, W) or 34th St/Penn Station (1, 2, 3) are the closest subway stops

Discounted shops in New York

Century 21 (21 Dey St)

  • Hours: 7:45 am-9 pm, open until 9:30 Thursday and Friday. 10am-9pm Saturdays and 11am-8pm Sundays
  • Website: https://www.c21stores.com
  • Getting Here: the nearest subway stations are Cortlandt St (R, W) and Fulton St (4, 5)

TJ Maxx 

  • Hours: 9am-9:30pm Monday to Saturday, 10am-8pm Sunday
  • Website: https://tjmaxx.tjx.com
  • Getting Here: 18th St Station (1, 2) is the nearest subway stop

Nordstrom Rack 

Empire Outlets in Staten Island

  • Hours: daily 10 am-9 pm
  • Website: http://empireoutlets.nyc/
  • Getting Here: Empire Outlets is located at the Staten Island Ferry, making it really easy to get to from Manhattan

How to Get Around New York

The best way to get around New York City is by subway. If you’re in town for more than 24 hours, then purchase a multi-day MetroCard, which will allow you to ride unlimited times for 7 or 30 days.

5 days in New York

How to Get To and From the Airport 

There are three airports in the NYC area. If you’re flying internationally you will fly into either JFK (in Queens) or Newark (in Queens). Here’s how to get into the city by train. Of course, you can always take a taxi or prearrange a car, but that will be much more expensive. With multiple people, a taxi or a shuttle service (a shared shuttle bus) can be about the same as taking the train, and way less hectic.

From JFK

From JFK, the AirTrain runs to Jamaica Station, where you will connect with the LIRR into Penn Station. 

From Newark

The AirTrain services the terminals to Newark Liberty Airport Station. There, you’ll switch trains to an NJ Transit train for New York Penn Station (**NOT Newark Penn Station). At NY Penn Station, you can change to a subway or get a cab to your final destination. The entire train from Newark to the city will be about 30 minutes. 

Oculus - 5 day New York itinerary
Oculus subway station

Passes in New York

If you plan to explore museums, visit some of the top sightseeing in New York, and travel around the city, then you should look into this sightseeing pass. It includes entry to some of NYC’s top attractions, like Top of the Rock, the 9/11 Museum, the Met, MoMA, Statue of Liberty, and more/ You can include a MetroCard as well. 

Check out my full review about the New York Turbopass here. 

Tipping in New York

Travelers from other countries often don’t understand the tipping culture when traveling in the US. Wait staff (restaurant servers, bartenders) don’t earn minimum wage – they rely on tips to make up their paycheck. Tour guides, cab drivers, doormen, housekeeping, and other service industry workers also expect tips. This can be daunting for someone who’s never tipped before, so here are some… tips.

One: In general, 15-20% of the total bill at a restaurant is considered a reasonable tip. You could go lower or higher if the service was really bad or really good, but in general, $15-20 on $100 is perfectly fine. At a bar, the standard is $1-2 per drink ordered. 

Two: Tips are not automatically added to your bill, so you will have to do the math when you get the bill. You will see the bill, leave your credit card, and when the server brings your card back, you will add the tip and sign the bill. If you are paying cash, you should add your tip into this and leave enough cash to cover both bill and tip. Some places prefer tips in cash, so if you have small bills with you, leave them on top of the credit card receipt.

Three: Housekeeping and hotel staff expect tips as well. Plan $2-5 per day for housekeeping, and $1-2 for a doorman hailing a cab for you.

There is so much to see and do in New York, and its a really fun city to explore. Whether you want to go shopping, to dine, or to revel in the city’s culture and history, there is something for everyone in New York City!

 

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