4 or 5 days New York itinerary – 3 plans with free self-guided walks

A one-size-fits-all approach does not work.

This guide includes not only one plan for a 4 or 5 day New York itinerary, but three options that suit families, couples, or with a bit of everything, including free activities and walks.

Suggesting a romantic sunset cruise to families with children or the Children’s Museum to couples makes little sense.

Adults and active couples will enjoy the third New York itinerary, which offers a bit of everything in a more dynamic way.

Let’s get started.

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4 or 5 days New York itinerary – In a nutshell

With 4 or 5 days in New York, you will be able to explore most of the attractions of Manhattan, the central borough, including a few little gems.

You can even think to explore other boroughs in your 4 or 5 days New York itinerary, like Brooklyn, Bronx or Queens.

Across the above four major boroughs, there are a total of 472 stations on 27 different subway lines. So easy to get around.

The fifth borough of New York, Staten Island, can be reached by ferry.

If you are not familiar with the boroughs and the areas of Manhattan, the heart of the city, I suggest having a quick look at the maps below, at the end of this post.

I this guide I have marked Day 5 as optional, to bypass (or swap) if you have only a 4 days New York itinerary.

4 or 5 days New York itinerary for couples: This is the perfect length for a stay in New York. You will get to experience so much. Start with Lower Manhattan and Midtown, where you will find a few iconic attractions, like the Empire State Building, of course, and a few hidden gems, like the most expensive toilette in the world (free to access) in the fancy Greenwich. You will have enough time also to visit other boroughs, like Brooklyn and the amazing Bushwick collective. Read below a detailed daily plan for 5 days in New York for couples
4 or 5 days New York itinerary for families: New York is such a great fun for families travelling with kids. There are so many attractions thought for the little ones. You can visit 2 Children Museums, both very interactive and unique in their own way. SPYSCAPE is another museum to add to your list, actually interesting for any age, I would say. Spending a day in Central Park is another popular option, with a visit to the zoo too. Read more below for the best family itinerary with morning and afternoon programs for 5 days in New York.
For a bit of everything: this is an itinerary for the more dynamic people. Indeed, there is more walking involved, however, you will get to experience so much. Start with the Edge observation deck, then the instagramable Vessel, a beehive of stairs that reminds the Harry Potter Hogwarts School of Witchcraft and Wizardry. Read more below for the most comprehensive plan for 5 days in New York

I have also created, and shared, a map with all the things to do and places to visit in New York

4 or 5 days New York itinerary for couples

Day 1 Viewpoint & Lower Manhattan

Take off on a high note with your romantic getaway.

And I do not just mean this as an expression. You can only truly grasp the scale of this never-ending beautiful city by experiencing it from a high point.

There are three options for you:

The most dramatic and romantic way to see New York is by helicopter. According to your choice of route, the flight lasts 15 to 30 minutes. This will be an unforgettable experience in the Big Apple
the Edge Observation Deck boasts one of the highest vantage points in the world. The observation platform has a transparent floor, enhancing the thrill factor
the Empire State Building: arguably the most iconic art déco building in New York, and maybe the world. Enjoy the view from the 102nd floor.

Helicopter Tour Empire State Building Edge Observation Deck

Spend the rest of the day exploring Lower Manhattan, but do not plan on seeing everything. A week would not be enough for that!

Consider a small area instead.

Enjoy an organised tour of the surrounding neighbourhoods of SoHo, Little Italy, and Chinatown, lead by a local expert.

Lasting 2 hours, you will see so much of each of these city neighborhoods, and you will get to know a few interesting and funny facts.

Alternatively, explore one of the cultural epicenters of the bohemian lifestyle, Greenwich Village.

Despite the Village’s full gentrification happened in the last 2-3 decades, it is still a charming, romantic and characteristic neighborhood.

You can follow this free self-guided walking tour with a map that comes with 12 stops, a few iconic sights, and a few hidden gems.

Another option is to take an organized walking tour of Greenwich Village that begins at Waverly Place and visits popular sites such as the Alan Poe House and the Washington Square Hotel.

Marie’s Crisis, an iconic bar with live piano music and cocktails, is a great place to grab a late cocktail.

SoHo, Little Italy & Chinatown Greenwich

Day 2 Statue of Liberty & World Trade Center

Begin your day by visiting the Statue of Liberty, probably the most iconic statue in the world.

You may not know that the Statue of Liberty was given as a gift to the USA by France to boost the relationship between the two countries.

The statue brings together visitors from all over the world annually.

It has a restaurant at the crown of Lady Liberty and a museum on the ground floor.

Wear some comfortable shoes, if you plan to walk up to the top.

As you learn about the history of this iconic landmark, you can take memorable photos of the breathtaking NYC skyline.

This organized tour combines a trip to the Statue of Liberty with a visit to Ellis Island.

From 1892 to 1924, Ellis Island served as the immigration gateway for over 12 million immigrants.

Enter the immigration center, which has been so well preserved that it appears to have recently been used.

By 3pm, you should be back in Manhattan.

Two subway stops north will bring you to WTC Cortlandt where you can see:

the magnificent World Trade Center Train Station, a masterpiece of architecture
Ground zero, in the former foundations of Twin Towers
the National September 11 Memorial Museum
the Mural Project, if you are keen on street art

Close your stay in New York with a sunset cruise in the bay aboard a schooner.

Statue of Liberty and Ellis Island Sunset Cruise

The Statue of Liberty with New York City in the background

Day 3 Guggenheim & Midtown

The Guggenheim Museum should not be missed on any trip to New York.

The building itself, designed by Frank Lloyd Wright, is an architectural masterpiece world-famous for its curved lines.

Then inside you will discover one of the biggest contemporary and modern art collections in the world.

Solomon R. Guggenheim founded this museum in 1939, known at the time as the Museum of Non-Objective Painting.

What makes it stand out is the six stories in a spiral ramp design. It circles an open space lit up by a glass dome supported by stainless steel.

The Guggenheim holds a vast collection of 20th century art pieces. Some of the work at the museum includes art from Picasso, Joan Miro and Kadinsky.

To save time, skip the ticket line by buying your tickets in advance.

The Guggenheim Museum is so vast that you can easily spend the entire day.

My suggestion here is to spend the morning and then have a late lunch & coffee outside the museum (Dig Cafe is a nice, cool, clean and affordable place just a few blocks away).

Spend the remaining part of the day in Midtown.

Take the subway to Grand Central/42 St to see and/or visit a few iconic places like:

Chrysler Building: the 1930 art déco skyscraper, once the tallest in the world, symbol of New York
Grand Central Terminal: famous for its grand facade and the main concourse, used as film set in so many movies.
New York Public Library: an impressive 1895 building, with the famous reading rooms with arched wood ceiling

Keep walking direction west to the 7th avenue, famous for its shopping.

Turn right and you will see Times Square.

Guggenheim Museum

Day 4 Brooklyn

There is more to New York than just Manhattan. New York City is actually divided into 5 boroughs, Manhattan being the smallest.

On Day 4, Brooklyn is the sole focus.

Begin your walk with the Brooklyn Bridge, built in 1883, and take a lock of love with you.

Visit some of the attractions in downtown Brooklyn while walking through the streets.

Then you have the option of taking the subway to Coney Island, a popular summer destination, or you can visit Bushwick, the neighborhood beset with street art.

A detailed self-guided walk through Brooklyn with a free map can be found here.

Below are few of the borough’s most interesting attractions mentioned in the walk, including a couple of hidden gems.

A former subway station, converted into the New York Transit Museum
the Mosaic House, a hidden treasure in the heart of Brooklyn
Bushwick Collective, one of the most impressive murals and street art installations in the world

The Bushwick neighborhood is also home to some really great bars, restaurants, and clubs where you can easily spend the entire night having a good time.

Alternatively, if not too keen on walking the entire day, join this Full-Day NYC Boroughs and Coney Island Bus Tour that goes through Harlem, Bronx, Queens, Brooklyn and Coney Island.

Brooklyn self-guided walk 4 Boroughs bus tour

Before going into the optional day 5, here are a few accommodations that are perfect for couples and the organised experiences I have suggested here for couples

Accommodations and experiences for couples:

Best Hotels: Iberostar 70 Park Avenue (one of the best value in New York, in Midtown, highly recommended), Equinox Hotel Hudson Yards (Lux in Midtown), Walker Hotel (mid-range in Lower Manhattan)
Best Boutique Hotel: Moxy NYC East Village (boutique great value, in Lower Manhattan)
Hostels & Cheap: Shared Room (cheap bunk bed)
Organised experiences:

Day 5 (optional) Central Park

It is time to explore Central Park, the Green Lung of Manhattan.

As you may already know, this is a huge 843 acres urban park, one of the biggest in the world.

Start your exploration from the souther side and go north.

There are many possible paths and ways you can choose from.

In this self-guided stroll, I have described a walk that goes through 12 lovely stops, including a couple of little gems.

The walk includes also 2 playgrounds, that you can easily skip, and a cafe for lunch.

You can also decide to rent an e-bike to have an easy ride around, probably the best way to explore most of the park.

Once finished, you can either decide to call it a day and go back to your accommodation or explore a bit of Harlem, bordering the northern part of Central Park.

Central Park self-guided walk Bike rent in Central Park

Approaching the Bow Bridge in Central Park

Check more photos below of a 4 day New York Itinerary.

4 or 5 days New York itinerary for families

Day 1 Midtown Manhattan

Your family’s vacation begins in New York’s Times Square, in the heart of the city.

Take some pictures with the kids in one of the most iconic spots of the Big Apple; they will last a lifetime.

Walk 3-4 blocks north-east to the Top of The Rock, next to the Rockefeller Center, for a 360-degree view of New York City.

If visiting during the winter, you can also rent skates at the iconic ice skating rink.

Dos Toros Taqueria offers cheap and quick Mexican food.

In the afternoon, head to the pier to catch the boat for a New York Harbor cruise.

They usually leave at 3pm (check the website for the updated timetable) and in 2.5 hours you will circumnavigate the island of Manhattan.

You will have beautiful views of the skyline with an insightful narration by a local guide.

A great fun for the whole family, doesn’t matter the age.

New York Harbour Cruise

Ferry Cruise to see New York City from the Hudson River.

Day 2 Central Park & Museum of Natural History

The morning of the second day in New York is ideal for visiting the most famous urban park in the world, Central Park.

Visiting this park is a must for any family travelling with young children.

Central Park is 843 acres of gorgeous scenery, magnificent lakes, lovely walking paths, and some of the city’s best playgrounds.

Take a stroll along the Gapstow Bridge and the Hallett Nature Sanctuary in the southern part of the park.

Next, visit the Central Park Zoo for a couple of hours.

Finally, don’t miss Bethesda Terrace and the Adventure Playground, so popular with kids of all ages.

You may want to check out my complete self-guided walk to see the above Central Park attractions (with a free map).

Everything about Central Park is great except the restaurants, bars, and cafes.

For this reason, it’s a very good idea to walk one block to Patsy’s Pizzeria on the West Side, which is a great place for kids to have lunch.

Take a short walk north after lunch to reach the American Museum of Natural History, made famous by Ben Stiller in the Night at the Museum saga (watch the movie before visiting New York).

This is the largest natural history museum in the world.

It comprises over 25 interconnected rooms and sits on 4 blocks of the city.

The museum is arranged with many interactive exhibits to engage children in every room they visit.

Many of us love dinosaurs and the museum holds one of the largest collections of fossils to learn from. It has over 6 halls to tell the history of dinosaurs.

If you want to learn about how people from different parts of the world live, check out the Hall of Biodiversity.

There is a Hall of African Peoples, Hall of Ocean Life and even corners to learn about gems and minerals.

Lovers of astronomy can visit the Heilbrunn Cosmic Pathway in the Rose Center for Earth and Space.

It tells the story of how the universe has evolved over 75 million years.

There is so much to see, expect an afternoon of fun and learning.

On the weekends and school holidays, buy your tickets in advance because it gets quite often sold out.

Museum of Natural History Ticket

Day 3 Statue of Liberty & Battery Park

It is time to visit another iconic destination of New York, the Statue of Liberty.

Join this 4 hours Statue of Liberty Tour that will take you also to Ellis Island, the formal immigration gateway in service till 1924.

As America continued to receive visitors from all over, they walked into the country through the steel and glass canopy in Ellis Island

Take a walk where the forefathers once stood and be amazed. Check out the Ellis Island Immigration Museum.

While there, there are video and audio components of the tour that will make it fun for the kids to learn.

There are film screenings of stories about Ellis Island. A park ranger offers a small introduction to the history of the place before the screening.

The park is very scenic and you can set up a picnic spot after your tour.

Trips start either at 9am or 11:30am in the morning (check the website for the latest timetable)

With the spare time you have left in the afternoon, you can think of visiting the Battery Waterfront Park where you will find the 1811 Fort Clinton.

This was the first immigration center, used till 1890 when Ellis Island took over.

A staggering 8 million people were processed in Fort Clinton.

In the Battery Park you will find also the SeaGlass Carousel, always a great fun for the little ones.

Statue of Liberty & Ellis Island Tour

Day 4 Children’s Museum & SPYSCAPE

This is going to be a day with lots of fun for children of any age.

In the morning, head to the Children’s Museum, on the West Side of Manhattan

What started as a neighbourhood organisation grew into a kids space that welcomes hundreds of thousands of visitors annually.

One thing kids can do is an art scavenger hunt, which lets them play while learning more about art.

There are dance and music sessions to boost the mood, movement and creativity of visitors.

Superpowered Metropolis: Early Learning City is a popular exhibit where visitors step into a comic book version of NYC and act as superheroes!

Inside Art is another exhibit that holds so much mystery and wonder. Walk under and look through the unique installations.

There are murals, illustrative portraits and so much more here.

Dynamic H2O is an outdoor exhibit that lets kids learn firsthand about the NYC water system.

There is a 22-foot interactive water table to enjoy while at the CMOM.

In the afternoon, have a visit to SPYSCAPE, to discover the world of spying in an interactive way

SPYSCAPE is on 60,000 square feet and holds 7 experience zones for guests.

As you proceed with the tour, find out your secret powers through spy challenges put together by a former lead British Intelligence trainer.

Some challenges include decryption, deception, surveillance and special ops.

Lovers of James Bond or Agent 007 will appreciate the projection mapping of this exhibition.

Here, you get to interact with the actual Aston Martin DB5 from the famous movies.

There is also a room where you can learn about the Enigma machines, microscopic bugs and many other gadgets.

You will leave here feeling like you can save the world!

Before going into day 5, here are a few accommodations that are perfect for families and the organised experiences I have suggested here for families

Accommodations and experiences for families:

Best Hotels: Trump International (Lux), La Quinta by Wyndham (mid-range) both of West Side, close to the Central Park
Best Airbnb: West of Times (1BR and 2BR), Near Empire State (1BR and 2BR) both very central in Midtown
Organised experiences:

Inside the formal Immigration Center of Ellis ISland — Inside the formal Immigration Center of Ellis Island

Day 5 (optional) Children’s Museum of the Arts

Start in the morning with a visit to the Children’s Museum of the Arts, in Lower Manhattan.

Creativity begins and should be nurtured from a young age.

The Children’s Museum of the Arts or CMA is one place where kids can check out art from other kids.

The CMA started in a boho studio back in 1988. It has steadily grown to a collection of over 2000 exhibits from kids around the world with works spanning over a century.

The major ongoing project is a digital commons known as the Look Make Show.

It is a digital animation project for educational purposes.

Always check in advance the updated opening time on the museum website.

In the afternoon, you have 3 options:

ARTECHOUSE in the Chelsea neighborhood. Your kids will be fascinated by this impressive exhibition based on projections and reflections (buy your tickets in advance)
National Museum of Mathematics, dedicated to all kids with interactive exhibits
Bryant Park for ice skating, in winter

Check more photos below of a 4 day New York Itinerary.

Central Park in winter at the rink close to the Zoo

4 or 5 days in New York for a bit of everything

Day 1 The Edge, the Vessel and a cruise

Start your vacation in New York from an elevated point, The Edge, to have a 360 degrees view of the Big Apple.

Part of the observation deck floor is in sea-through glass, which is absolutely a great fun, unless you have a fear of heights.

Keep touring Midtown West by walking a few minutes to the nearby Vessel.

This is an architecture jewel that you may have already seen it in a few photos on the socials.

It is a sort of gigantic beehive/doner kebab, 150 foot tall (around 45 meters), made of metal stairs that seem not having a beginning or an end.

It reminds me a bit of the stairs in the Henry Potter school.

You can walk up or take an elevator. Making a few photos there is a must.

Another interesting spot to finish off in the morning, always in the same area, is Citrovia, an interactive installation featuring a garden of gigantic lemons and trees.

An awesome location for a few shots. It’s also free to enter. Who is going to complain about that?

In the afternoon, take the 3 hours Official NYC Architecture Cruise, leaving from the Pier 62, walking distance from Citrovia.

The cruise is on a beautiful 1920’s-style yacht. You will feel suddenly in a time machine, although the skyline will remind you we are in the 21st century.

The tour is guided by architects and members of the American Institute of Architects New York Chapter (AIANY) with plenty of information on the history, planning, design and engineering of the city.

This cruise has been rated as one of the most interesting tour in the Big Apple.

The departure time varies based on the season and day of the week.

In fact, it may run only in the morning or the afternoon, o both (check the website for the timetable). If needed, re-plan the day accordingly.

3-hours Architecture Cruise

Day 2 Harlem & Park Avenue Armory

Make your way to Harlem, north of Central Park, for a unique experience. Stay there the whole day or just for the morning.

Located off of the beaten path, this area of New York is rich in culture and history, besides being a great place to explore.

There is so much to do in Harlem. You can

take part in a unique gospel service in New York
find a great shopping area with a touch of black culture along West 125th Street
visit the National Jazz Museum
enjoy street basketball at the best court in the world
listen to live jazz

You can follow this free self-guided walking tour around Harlem, complete with a map, that I draft with 12 interesting stops

As you get to know the neighborhood, stop along the way for lunch.

You can also catch a gospel performance at Ginny’s Supper Club if you missed the morning gospel service at the church (usually in the morning).

Visit the Park Avenue Armory (subway to Lexington/63st) on the East Side of Manhattan if you still have time left in the afternoon.

Discover the monumental rooms and the incredible wood ceilings of this grandiose building.

You can also spend the rest of the evening/night at Park Avenue Armory (See website for current events).

Day 3 Midtown

Day 3 is fully dedicated to Midtown Manhattan, south of Central Park.

The walk starts in Times Square, the heart of New York (check out my shared Google Map).

Midtown Manhattan Walking Tour (self-guided) – Check and download the Google Map

The day walk itself is not as long, only 3.5 miles (around 5.5 km), however, there are so many places to see and attractions to experience.

Start at Times Square, then stop at the New York Public Library, the Grand Central Station and the Chrysler Building.

Then, visit the Empire State Building, one of New York’s most beautiful art déco buildings, which features a striking observation deck on the 108th floor and a gallery on the 86th (skip-the-line tickets here).

Follow the 5th Avenue direction south for a few blocks and you will arrive at the spectacular 1902 triangular Flatiron Building, designed by the architect Daniel Burnham.

This was the tallest skyscraper in New York till 1902. Today, it is world famous for its unusual shape and its Neo Renaissance style.

Walk two blocks east to Fotografiska, so beloved by the photography community.

They host regular photo exhibitions in an iconic Renaissance gallery.

Do you have still an hour or two to spare?

Have a visit to the boutique Poster House, a small museum dedicated to the history of graphic design in political and advertising posters.

Day 4 MoMA & Midtown

In New York, you can visit many museums and galleries as you are probably already aware.

However, there is one museum in particular that stands out: the Museum of Modern Art, or MoMA.

This is where I suggest spending the morning of the 4th day in New York.

It has kept its doors open since 1929. It was initially a place for temporary exhibitions of contemporary art.

The demand for this type of art was so high that a permanent exhibit began in 1952.

The Museum holds an extensive collection of sculptures, paintings, multi-media art and films to quench the thirst of art lovers.

There are important pieces of art under the MoMA roof, like Vincent Van Gogh’s ‘Starry Night’.

You will see also Pablo Picasso’s ‘Girl Before the Mirror’, which was purchased for $10,000 back in 1938.

The celebrated sketch piece ‘Before the Mirror’ by Max Beckmann was gifted to MoMA by one of its pioneer board members, Paul Sachs.

I highly suggest buying the tickets in advance if visiting on weekends. You will avoid the usual long queues.

Spend the afternoon visiting the World Trade Center, starting with Ground Zero.

As a result of the September 11 terror attacks, the famous landscape of New York City changed forever

Ground Zero is the place where the Twin Towers and other 5 buildings once stood.

The area of Ground Zero is now called One World Trade Center.

The new name was given by New York City mayor Michael Bloomberg in 2014.

The 9/11 Memorial Pools will certainly catch your attention.

They have been positioned where the Twin Towers once stood to commemorate the victims of the 9/11 attack as well as the 1993 World Trade Center bombing.

Make sure to visit also the National September 11 Memorial Museum for an extensive understanding of all it happened in that day that changed the world.

You can also join this Organised Tour of the Memorial to discover 9/11 through the eyes of guides who have a personal connection to this tragedy

Before going into day 5, here are a few accommodations and the organised experiences I have just suggested

Accommodations and experiences: