Skip to Content

5 Day NYC Itinerary

5 Day NYC Itinerary

This 5 Day NYC Itinerary brings together all of the city’s must see sites. Follow this itinerary to experience all of the best museums, historical sites, parks, and things to do in New York City. This New York City itinerary is designed so that you can walk from place to place exploring a different part of the city each day.

One quick note, if you are going to be in New York City at Christmastime, follow the link to my post of 250+ Things to do in New York City and there is an entire section devoted to Christmastime activities! You could easily spend an entire day in New York City checking out Christmastime events and activities!

My 5 Day NYC Itinerary:

NYC Itinerary Day 1: Lower Manhattan

The first day of this NYC itinerary is all about seeing some of New York City’s highlights.

Castle Clinton

Start your day by going to the Statue of Liberty and Ellis Island. I definitely recommend purchasing tickets in advance. You will take the ferry from Battery Park to Liberty Island and then Ellis Island. The ferry leaves from beside Castle Clinton, a National Monument and fortification built to prevent British invasion. You can easily add this to your itinerary if you want.

Statue of Liberty

There different types of tickets available for the Statue of Liberty, giving access to different parts of the monument. You need a specific ticket to go all the way to the crown. An hour or so should be enough time to spend at Liberty Island before going to Ellis Island.

Ellis Island

Ellis Island offers several different tours and experiences. You can watch films about the history of Ellis Island, trace your ancestors journey to Ellis Island at the research center, sign up for the hard hat tour of the abandoned hospital, or go on an audio tour. You may want to spend just an hour at Ellis Island, or you could spend half a day experiencing everything.

Charging Bull and Fearless Girl

The walk from Battery Park to the Oculus will take you past the Charging Bull statue and The Fearless Girl.

The Oculus

The Oculus is a train station/shopping center that cost $4 billion to build. Have lunch at The Oculus, or just stop in for the photo opportunity – it is an architectural wonder.

9/11 Memorial and Museum

Next visit the 9/11 Memorial and Museum, which are located just beside The Oculus.

Dinner

If you need a recommendation, I have lots in this post about 250+ Things to do in New York City.

What to do in Midtown Broadway and Times Square

NYC Itinerary Day 2: Times Square / Rockefeller Center / Midtown

The day 2 itinerary is all about Midtown and features some of the city’s most well known sites.

Top of the Rock

Your first stop is Top of the Rock – this is dependent on the weather – it is definitely best to go on a clear day. Top of the Rock offers incredible views of Central Park to the North and the Empire State Building to the South. I recommend going to Top of the Rock instead of the Empire State Building because the view of the Empire State Building from Top of the Rock can’t be beat. Top of the Rock is a popular attraction, so it is best to purchase tickets in advance.

Rockefeller Center

After you have been to the top of Rockefeller Center, it is time to explore Rockefeller Center. Tour Rockefeller Center, NBC Studios, or Radio City Music Hall.

Museum of Modern Art

The MoMA is just three blocks north of Rockefeller Center. This is where you can find works by Warhol, Pollock, Dali, Monet, Matisse, and Picasso. The most famous painting in the collection is probably Van Gogh’s The Starry Night.

Grand Central Station

Grand Central Station is about a 15 minute walk from Rockefeller Center, and it is far more than a train station. See the Main Concourse with its celestial ceiling, visit the Whispering Gallery, admore the Vanderbilt Hall chandeliers,  or take a tour.

Grand Central has several dining options, including two sit down restaurants upstairs, and a dining concourse downstairs which is home to a Shake Shack, Magnolia Bakery, and the Oyster Bar. If you want a drink, head to the chic (and pricy) Campbell Apartment for a cocktail.

New York Public Library

You may remember New York Public Library from the Sex and the City movie, it was where Carrie was supposed to marry Big. Even if you aren’t a SATC fan, you will want to see the stunning NYC landmark. Visit the lions guarding the entrance, and once inside see the Rose Reading Room. There are free tours available, one focuses on the building and the other on the exhibition.

Times Square

Next, go to Times Square. You may just want to walk through, or you might want to explore the NFL Experience, National Geographic Encounter: Ocean Odyssey, Gulliver’s Gate, the Hershey’s store, and the M&M’s store.

See a Broadway Show

End your day by seeing a Broadway show, comedy show, or going to a television show taping. Note: most Broadway shows are closed on Mondays. Tickets to television tapings need to be arranged in advanced. You can buy same-day tickets to Broadway shows at the TKTS booth.

Dinner

If you want to eat before or after the show, check out a classic NYC restaurant like Sardi’s or Joe Allen. If you want a feast and don’t mind going to a touristy spot, check out Carmine’s. You can find more recommendations in my guide of what to do in Midtown.

The Best Things to Do in New York City - A Guide of 250+ Things to Do

NYC Itinerary Day 3: Upper East Side

Day three of the NYC itinerary is focused on seeing the Upper East Side, which is home to many of the city’s best museums, and some excellent shopping. I listed both The Met and the Guggenheim, but you will likely only have time to see one.

The Metropolitan Museum of Art

The Met is New York City’s biggest grandest art museum. An art lover could easily spend half a day in the museum. Highlights include “Washington Crossing the Delaware”, plus works by Van Gogh, Monet, O’Keeffe, Rembrandt, Raphael, and Goya.  I recommend visiting The American Wing to see one of the world’s best collections of American Art.

The Guggenheim

This museum is just a few blacks north of The Met, and it is devoted to displaying art from the 20th century onward. Most the museum is dedicated to showing temporary exhibitions, so it is best to check to make sure the current exhibitions interest you before you go.

Afternoon Tea at the Plaza

The Plaza is one of NYC’s most luxurious hotels, and it is one of the best places for Afternoon Tea. Afternoon Tea is served at the Parm Court, a beautiful bright airy space decorated with palm trees.

Central Park

An NYC itinerary isn’t complete until you add Central Park! Central Park is massive, so you might want to rent a bike if you want to see all the sites. Central Park’s highlights include Strawberry Fields, Alice in Wonderland Statue, Central Park Carousel, Bow Bridge, the Bethesda Terrace, Bethesda Fountain, Belvedere Castle, the Pond, and the Shakespeare Garden.

Shopping

Madison Avenue and Fifth Avenue are home to some of New York City’s best shops. Plus, the shops on the Upper East Side tend to be less crowded than the ones in Midtown.

Gracie Mansion

The Gracie Mansion is a Federal-style mansion within Carl Schurz Park. It is the official residence of the New York City mayor. It is only open for tours on Mondays and space is very limited.

The Roosevelt Island Tram

The Roosevelt Island Tram offers wonderful views of Manhattan. You may want to just take the tram to Roosevelt Island and back, or you could opt to explore the small residential island which is home to a lighthouse and an abandoned smallpox hospital.

Dinner

I love Up Thai, JG Melon, and Orsay. You can find more recommendations in this guide of what to do in the Upper East Side.

Drinks

And if you want to go out after dinner, check out the list of bars in my post about 250+ Things to do in New York City.

What to do in Union Square area | See the Flatiron Building

NYC Itinerary Day 4: Chelsea / West Village / East Village / Soho

You have seen most of Manhattan’s major sites, and day four is more about exploring the city like a local.

Walk the High Line

This 1.45 mile elevated park runs from West 34th Street to the Meatpacking District. The High Line has gardens and amazing city views. I recommend starting at the north end and walking south.

Chelsea Market

The Chelsea Market is a food hall just beside the High Line and a perfect place to get lunch. The market has dozens of restaurants, serving up everything from sushi to currywurst. There is also a location of Artists & Fleas, a popular flea market / locally produced goods shop within Chelsea Market.

Walk through Greenwich Village

Greenwich Village just might be Manhattan’s prettiest neighborhood. It’s the perfect place for a stroll as you work your way East.

Washington Square Park

Stop by Washington Square Park to see the famous arch and continue North.

Explore Soho

Soho is a bustling area for shopping and restaurants.

See the Flatiron Building

Take the 4 or 6 train from Spring Street up to 23rd street and then walk a block East to the Flatiron Building. The Flatiron buiding is one of Manhattan’s most recognizable buildings.

Rooftop drinks at Eataly

Eataly is just across the street from the Flatiron Building and their rooftop bar is the perfect spot for a happy hour drink.

Dinner at Casa Apicii

I love this Italian restaurant that is tucked away inside an old townhouse. The pastas are delightful and the space is so pretty. You can find more restaurant recommendations in my guide of what to do in Greenwich Village and Chelsea.

NYC Itinerary Day 5: Brooklyn

There is so much to see and do in Brooklyn and it tends to be less crowded than Manhattan.

The Brooklyn Bridge

Walk across the Brooklyn Bridge, or rent a bike and ride across. This will offer great photo opportunities.

Brooklyn Botanic Garden

Once you are across the Brooklyn Bridge, take the 2 or 3 train to Franklin Ave and walk tothe Brooklyn Botanic Garden. This garden is known for its cherry blossoms, magnolia trees, and roses. It is small enough to see in a couple of hours.

Prospect Park

After the Botanic Garden, walk through Prospect Park to the G train. Take the G train to Williamburg, getting off at the Metropolitan Ave stop.

Williamsburg

Walk east down Grand Street to Bedford Avenue, these two streets are lined with locally owned boutiques and restaurants.

Cocktails at The William Vale

The William Vale is a new hotel in Williamsburg and their beautiful rooftop bar, Westlight, has one of the best views of the Manhattan skyline.

Dinner at Cafe Mogador

One of the best things about New York City is that you can try cuisine from all over the world. Cafe Mogador is an excellent Moroccan restaurant, and it can often be hard to find Moroccan food, so take advantage of this opportunity to try it.

Read More NYC Travel Guides:

250+ Things to do in New York City
A 3-5 Day New York City Itinerary

NYC Neighborhood Guides
NYC Packing List

26 Foods to Try in New York City
Cheap Meals in NYC
Gossip Girl Filming Locations

Sex and the City Filming Locations
What to do in Lower Manhattan
What to do in Soho
What to do in Greenwich Village and Chelsea

What to do in the Meatpacking District
What to do in Tribeca
What to do in Union Square

What to do in Midtown
What to do in the Upper East Side
What to do in the Upper West Side
What to Do in the West Village
What to do in Murray Hill, Gramercy, and Kip’s Bay
What to do in the East Village
What to do in the Lower East Side

What to do in Brooklyn
What to do in Williamsburg
What to do in DUMBO
What to do in NYC at Christmastime
What to Know about Visiting New York City
Which NYC Airport to Fly Into
24 Hours in NYC and a Visit to Roosevelt Island

Want to save this NYC Itinerary for later? Here is an image to pin:

What to do in NYC : A detailed 3-5 day NYC Itinerary | This 5 Day NYC Itinerary brings together all of the city's must-see sites. Experience all of the best museums, historical sites, parks, and things to do in New York City. This itinerary is designed so that you can walk from place to place exploring a different part of the city each day. #nyc #newyorkcity

thekittchen