THE ULTIMATE 5 DAY NEW YORK CITY ITINERARY

New York City is one of the, if not the, most popular cities in the entire world. From the Statue of Liberty to the Empire State building to being the home of Broadway, the Big Apple should be near the top of everyone’s bucket list.

You could spend a lifetime in New York City and still not get to experience all that it has to offer, but if you are able to visit for at least five days, you can get a well rounded taste for the city.

In this itinerary you will be able to see many of the city’s major highlights while also exploring the different neighborhoods. You’ll be doing lots of walking, and riding on a lot of subways, but it will be an experience you’ll never forget. Here is the Ultimate 5 day New York City Itinerary.

Day 1 - Manhattan

Rockefeller Center - Times Square - Broadway

Start off with a bang by seeing some of the city’s biggest attractions. Take the subway into the heart of Manhattan and where you will be able to see a lot in just a few hours.

ROCKEFELLER & TOP OF THE ROCK

One of my favorite things to do in New York City is to get an aerial of the city at the Top of the Rock. Open from 9am until midnight, this 360 degree view of New York will help you get an overview of the city where you can see sights like the Empire State Building, Central Park, and even the Statue of Liberty off in the distance.

There are three floors, both indoor and outdoor, that you can visit 70 stories above the ground. The tickets are a little steep at over $50, but it is worth it to see New York from this vantage point. I prefer it over the Empire State Building lookout because you can see the Empire State Building from this view, which is one of the more interesting buildings to look at from above. For a different perspective, visit at sunset or at night.

After you visit the Top of the Rock, you can get a tour inside Rockefeller Center, and learn more about the history of the building where they still film The Tonight Show and Saturday Night Live. If you are lucky enough to score tickets to one of these shows, prioritize that on your trip.

If you are visiting during the holiday season, you can see the giant Christmas tree illuminated and opt for an ice skating experience right in Rockefeller Plaza.

Right outside of the Rockefeller Center are a few more attractions worth taking a stroll past. These include St. Paul’s Cathedral, Bryant Park, and Radio City Music Hall. Carnegie Hall is nearby as well.

TIMES SQUARE & BROADWAY

After getting all of the Rockefeller out of your system, continue your day by walking over to Times Square. While it is super crowded and touristy, and you won’t catch locals dead here, it is still worth visiting to see it once in your life. I wouldn’t spend too much time here, but maybe take a walk past the illuminated buildings while experiencing the true hustle and bustle of the city.

In the evening, grab dinner in Hell’s Kitchen before seeing a Broadway Show. There’s nothing quite like seeing a Broadway show in New York City, and there are dozens of shows to choose from. Consider buying tickets in advance to secure seats.

Day 2 - Lower Manhattan

Statue of Liberty - Ellis Island - 911 Memorial & Museum - One World Observatory - Financial District - Tribeca

Today you will be seeing three of New York’s biggest attractions: The Statue of Liberty, Ellis Island, and the World Trade Center Memorial. It will involve a little bit of planning but will be well worth it.

STATUE OF LIBERTY

One of the world’s most well known statues, a visit to see the Statue of Liberty is mandatory when traveling to New York City. Get started bright and early by taking one of the earliest ferries to Liberty Island.

Once on Liberty Island, you can walk around the base of the statue, or if you bought tickets to explore the Pedestal or Crown, you can get a few different vantage points of the statue. For more information, check out Visiting the Statue of Liberty and Ellis Island.

There is a museum detailing the history and construction of the statue that you can visit before hopping back on the ferry over to Ellis Island.

ELLIS ISLAND

Once the arrival port for all immigrants moving to the United States, Ellis Island is now a museum where you can get a glimpse into what it was like for America’s early immigrants.

In the main hall you can sit on the benches where immigrants waited for inspections to be admitted into the country. There are tons of artifacts, photos, and information explaining the process of immigrating through Ellis Island. You can also search their database to look for ancestors that immigrated over.

For more information on visiting Ellis Island, please check out Visiting the Statue of Liberty and Ellis Island.

FINANCIAL DISTRICT

After hopping off the ferry in Battery Park, you will walk right through New York City’s Financial District. Home to the New York Stock Exchange, Wall Street, the Charging Bull Statue, and the Federal Reserve Bank of New York, a walk through the Financial District has some interesting sights to see.

911 MEMORIAL & MUSEUM & ONE WORLD OBSERVATORY

One of the more moving areas of the city, the 911 Memorial and Museum are not to be missed. Spend time remembering the disastrous events and all those lost in the terrorist attacks of September 11, 2001.

Afterwards, you can journey up to the observation deck in the One World Observatory for some of the best views across the city and over Brooklyn. The One World Observatory was created after the two towers collapsed, and is the tallest building in the United States. You can purchase your tickets both for the Museum and the Observatory online in advance, or in person, but I would recommend getting them in advance to save money and plan your day, as there is timed entrance for the Observatory.

TRIBECA

After a full day of iconic sights, spend your evening winding down in the neighborhood of Tribeca. Get dinner at one of Tribeca’s restaurants, or grab a drink near the waterfront in one of New York City’s nicest neighborhoods.

Day 3 - Manhattan

Museums and Parks - Greenwich Village

After two days of nonstop sightseeing, slow down a little bit today with parks and museums.

MUSEUMS

Start your morning off by checking out one of New York City’s most famous museums. The Metropolitan Museum of Art, aka The MET, is one of the world’s best art museums and features exhibits containing ancient art from nearly 5,000 years ago. Highlights include work from Picasso, Monet, and Van Gogh.

Just up the street from the MET is the Solomon R. Guggenheim Museum, aka The Guggenheim. The stunning building, designed by Frank Lloyd Wright, is home to world famous impressionist, post-impressionist, early Modern, and contemporary art.

New York is also home to MoMA, the Museum of Modern Art, which is a must visit if you are into art. This is just a 5 minute walk from Rockefeller Plaza and has artwork from some of the biggest artists in history including Pablo Picasso, Salvador Dali, Andy Warhol, and Vincent van Gogh, most notably his painting of “The Starry Night”.

All three museums are located right off Central Park, which is where you will spend the rest of your afternoon.

CENTRAL PARK

No visit to New York is complete without a stop at its most famous park, Central Park. The most visited urban park in the US, Central Park offers a serene landscape with stunning views of the city. Escape from the chaotic city by strolling through the park or renting a bike.

Starting from the 5th avenue entrance of the park, you will be first greeted by The Pond area: a scenic pond surrounded by trees and the Gapstow Bridge, which looks like something out of a fantasy movie.

Beyond the Pond you will pass by the Central Park Zoo and onto the Mall, which is a busy strip of vendors and street performers. Statues of famous writers line the walkway, as do benches where you can soak it all in.

Bethesda Terrace with its accompanying fountain is another gathering spot for visitors. Nearby is the Lake where you can rent a rowboat and explore the park by water. There are tons of sidewalks that can lead you down different paths as you explore this area.

Sheep Meadow is a must visit in Central Park as it offers one of the park’s most iconic views. With the green grass of the meadow in the foreground and the towering skyscrapers in the background, a stop at Sheep Meadow is worth it. This is also a great spot to relax, have a picnic, or sunbathe if the weather is suitable.

Another point of interest in Central Park is Strawberry Fields, a memorial created for John Lennon near the place where he lived and was murdered.

GREENWICH VILLAGE

Take the train downtown and spend the rest of your day exploring the vibrant neighborhood of Greenwich Village. Also known as simply The Village, it is one of the nicest areas of Manhattan and has a great vibe.

Take a stroll through down Bleecker and MacDougal streets, which are loaded with bars, restaurants, rooftops, and shops. Or if you’re still in the mood for more parks, visit Washington Square Park or Union Square Park. In the evening, take in one of the neighborhood’s restaurants, listen to live music, or opt for a stand up comedy show at the original Comedy Cellar.

Day 4 - Brooklyn

DUMBO - Brooklyn Bridge Park - Prospect Park - Williamsburg

Today you are exploring Brooklyn. If it were its own city, it would be the third largest city in the US, just behind Manhattan and Los Angeles. This area of New York City is connected to Manhattan via the stunning Brooklyn Bridge, and this is the first stop of the day.

DUMBO

Start in Dumbo where you can explore by foot. If you are visiting on the weekend, lookout for the Brooklyn Flea market that takes place in Dumbo.

Dumbo is also home to the iconic view of the Manhattan Bridge. If you love taking photos, like me, you’ll be ecstatic to get these shots.

BROOKLYN BRIDGE

Next, head to Brooklyn Bridge Park, which will give you incredible views of both the Brooklyn Bridge and the Manhattan Bridge. Take your time strolling around the Brooklyn waterfront, and grab some lunch with incredible Manhattan skyline views.

Walk or ride a bike across the Brooklyn Bridge to get a different perspective. With lower Manhattan looming in the background, the iconic Brooklyn Bridge is worth seeing up close and personal before moving onto Prospect Park.

PROSPECT PARK

Brooklyn’s version of Central Park, Prospect Park is a green oasis in the bustling city. Ride a bike through the park, or take a leisurely stroll and pass by tons of joggers, dog walkers, and cyclists escaping the city.

If you are visiting in the summer, the park has concerts and Smorgasbord Prospect Park takes place on Breeze Hill every Sunday through October with a plethora of food trucks.

WILLIAMSBURG

One of Brooklyn’s most popular and trendy neighborhoods, end your day exploring the streets of Williamsburg. Find a swanky rooftop restaurant, shop and admire street art on Bedford Avenue, grab a beer at the Brooklyn Brewery, or visit one of Williamsburg’s many parks. Williamsburg is full of fantastic dining options, bars, and shops to fill a whole day, so give yourself a few hours to take it all in.

Optional:

CONEY ISLAND

Take the train to the southern tip of Brooklyn and visit the kitschy Coney Island. The unconventional beach town offers a plethora of interesting activities. Take a ride on the Wonder Wheel ferris wheel, relax on the beach, enjoy the rides at Coney Island’s amusement park Luna Park, and make sure to get yourself a hotdog and stroll the boardwalk. With an aquarium, a circus, mini golf and Friday night fireworks, there are plenty of things for everyone to stay busy.

If you want to add in a trip to Coney Island, I would start the day early to pack it all in as you will be traveling about an hour each way from Dumbo / Williamsburg.

Day 5 - Chelsea

The High Line - Chelsea - The Empire State Building

On your final day in New York City, start your morning by exploring the neighborhood of Chelsea before visiting a few of New York’s most iconic spots.

THE HIGH LINE

Grab a coffee and a bagel before beginning your last day by walking along one of the most vibrant parts of the city, The High Line. Completely free to visit, walk along the once abandoned rail line and discover unique views of the city and Hudson River. It takes about 30 minutes to walk the line.

CHELSEA

After walking the High Line, enjoy the rest of your day in Chelsea & the Hudson Yards. If you want another aerial view of NYC over 100 floors high, check out The Edge. If you are looking for a bit of adventure, you can do the City Climb where you wear a harness and hang over the edge of the city.

Wander around the Little Island, an artificial park created on the Hudson River near Chelsea Piers and Little Winery. The Island is free to enter, and offers a sliver of solitude in the busy city. Little Island has food trucks, live music, beautiful gardens, and lots of interesting photo opportunities. Afterwards, you can visit the City Winery or find a nearby rooftop spot for a drink or lunch.

The Chelsea Market is another great spot to eat lunch, or spend time browsing for gifts. If you are visiting on a weekend, check out the Chelsea Flea Market. Take a stroll past Madison Square Garden, one of the most famous arenas in the world. If you are in town for a Knicks game or concert happening that night, consider attending a game or a show at the Garden.

EMPIRE STATE BUILDING

Cap off your incredible 5 days in New York City by visiting the city’s most famous building, the Empire State Building. If you already did the Top of the Rock, you’ve gotten the best views of the building itself. But the 360 open air observation deck at the Empire State Building gives a completely different perspective of the city.

You can visit the main deck on the 86th floor for $44 USD for adults, $38 USD for children, or opt for a combo ticket to the 86th and 102nd floors priced at $79 USD for adults, $73 USD for children.

Five days is not enough time to see everything this city has to offer, but it can definitely help you scratch the surface of this concrete jungle. By knocking out this itinerary you will have gotten a good feel for the city and will know where you want to spend your time on your next trip!