5 Days in New York: The Ultimate New York City Itinerary

About this New York City Itinerary

New York City is massive and the list of places to visit is long. We have been visiting New York City on a regular basis for the past 22 years. I went to graduate school in New Jersey and Tim and I would frequently day trip into the city. Since then, we try to visit New York City once a year, simply because we love this city. In fact, we even started and ended our around the world trip right here. To me, New York feels more like home than Baltimore, the city where I was born and raised.

In general, I grouped sites together based on their location in order to save you time walking and using public transportation. This will keep you from spending unnecessary time on the subway and from backtracking through the city.

You can do these days in any order.

The provided walking distances are the amount of walking you will do to get between sites. These do not include the amount of walking you will do inside of museums, art galleries, etc.

I do my best to keep the hours of operation and pricing up to date for each attraction, however, these can change at any time. I recommend getting updated hours and pricing for your dates of travel. The link to the official website is provided for each site.

New York City Itinerary: Day 1

One World Trade Center, the 9/11 Memorial, Staten Island Ferry, and SoHo

Walking distance: 1 mile plus 0.5 to 1 miles in SoHo

One World Observatory

One World Trade Center is the seventh tallest building in the world and the tallest building in the western hemisphere. This skyscraper stands next to the footprints of the original World Trade Center buildings that were destroyed in the 9/11 terrorist attacks.

The One World Observatory, which is the observation deck on One World Trade Center, is a great place to take in your first view of New York City. From here, you have awesome views of Manhattan, the Statue of Liberty, Brooklyn, Staten Island, and New Jersey. Plus, by being here early in the day, you get to beat the crowds and have a more pleasant experience.

View from One World Observatory | 5 Day New York City Itinerary 

View looking east from One World Observatory | 5 Day New York City Itinerary 

I recommend buying your tickets online in advance. If you purchase tickets online in advance, you will skip the ticket line but could still wait in line for the elevator to the Observatory. You have the option to pay more money to also skip the elevator to the Observation deck and the elevator back down to the lobby. You can also purchase skip-the-line-tickets through GetYourGuide (a great idea if they are sold out on the official website).

Cost: tickets start at $44
Hours: Get updated hours here
Getting Here: One World Trade Center is accessed from the World Trade Center station on the E line, the Rector Street Station on Line 1, the Fulton Street on Lines 4 and 5, or the Cortland Street Station on Line R.

9/11 Memorial Plaza

After your visit to the One World Observatory, spend some time at the 9/11 Memorial Plaza. The 9/11 Memorial Plaza is an 8-acre park where the World Trade Center Twin Towers once stood. The foundations of the Twin Towers have been converted into reflecting pools and the surrounding area is now a grove of trees.

9/11 Memorial and the Oculus | 5 Day New York City Itinerary 

9/11 Memorial Museum

At the 9/11 Memorial Museum, learn about the story of 9/11 through a series of exhibits, artifacts, and interactive technology.

Website: www.911memorial.org
Entrance Ticket: Entry tickets can also be purchased through GetYourGuide.

The Oculus

The Oculus, also called the World Trade Center Transportation Hub, is a brand new, state-of-the-art train station. It sits right around the corner from the World Trade Center. You know you are in the right spot when you see the brilliantly white, space-aged looking structure.

The Oculus | 5 Day New York City Itinerary 

The Oculus opened in March 2016. It connects the PATH (trains from Newark and Hoboken, New Jersey) to the New York City subway system. It is also a shopping mall and a place to grab a bite to eat.

It’s worth a quick visit and it’s free!

Lunch at Pisillo Italian Panini

Two blocks from the Oculus is a great little Italian sandwich shop. This is popular lunch spot for locals and business people working in the area. These sandwiches are enormous and can be split between two people.

Wall Street

On your way to Battery Park, wander through the Financial District and take a stroll down Wall Street.

Staten Island Ferry

A ride on the Staten Island Ferry is one of New York City’s best free things to do. During this ride, you have great views of the Statue of Liberty and the Manhattan skyline.

The ferry leaves from the Staten Island Ferry terminal, next to Battery Park. Simply get in line and board the next ferry. The ferry is enormous, with multiple decks and inside and outside seating.

I recommend taking a seat outside on the back of the ferry. From this point you can watch Manhattan slowly recede as you approach Staten Island. To your left will be the Statue of Liberty.

View from the Staten Island Ferry | 5 Day New York City Itinerary 

Ferries leave every 30 minutes and are more frequent during rush hour. A one-way trip takes about 25 minutes.

You are not permitted to stay on the ferry and ride it round trip. Once you are in Staten Island, exit the ferry, get back in line, and re-board the ferry. We were able to get right back onto the same ferry without having to wait for the next one (on a Monday morning in February).

The entire round trip ride takes about one hour.

Get the full details about the Staten Island ferry on the official website.

Spend the afternoon in SoHo

SoHo is a neighborhood in Manhattan that is home to art galleries, trendy shops, and restaurants. It gets its name from its location “South of Houston Street.”

Spend the afternoon wandering and shopping here.

To get to SoHo from the Staten Island Ferry Terminal using the subway, walk to the Whitehall Street Station. Take the R line four stations uptown to Prince Street.

For dinner, we highly recommend Piccola Cucina Osteria. This tiny restaurant serves traditional Sicilian food. We have eaten in Little Italy many times but this restaurant is so much better than any place in Little Italy. The food is amazing. It’s a small place so I recommend making a reservation in advance.

Soho | 5 Day New York City Itinerary 

For dessert, you have two options in the area. Just across the street from Piccola Cucina Osteria is Dominique Ansel Bakery. This bakery has unique desserts…how about trying a cookie baked in the shape of a cup and filled with milk? Yum!

One block from Piccola Cucina Osteria is Black Tap, a restaurant that is legendary for its gigantic milkshakes topped with cookies, brownies, and even slices of pie. If you want to take a cool food photo on Instagram during your trip to NYC, this is a good place to put on your list. Expect to wait in line for at least 30 minutes.

New York City Itinerary: Day 2

Art Museums, Central Park, Rockefeller Center, Times Square

Walking distance: 4 miles plus Central Park (an additional 2 to 4 miles)

Take Your Pick from Four Art Museums

There are a bunch of fabulous art museums in Manhattan. Spend the morning in the one that sounds the most interesting to you.

The Museum of Modern Art

The Modern Museum of Art (MoMA) has one of the world’s best collections of art from the 18th century to today. See The Starry Night by Van Gogh, The Persistence of Memory by Dali, and works of art by Matisse, Monet, and Picasso.

Website: www.moma.org

The Metropolitan Museum of Art

The Met is enormous. It’s so big that you can measure the size of this museum in acres (13 acres!!). Come see one of the best collections of ancient art from all around the world.

Metropolitan Museum of Art | 5 Day New York City Itinerary

Website: www.metmuseum.org

The Guggenheim Museum

This is another modern art museum. The building, which was designed by Frank Lloyd Wright, is also a work of modern art.

Inside the Guggenheim | 5 Day New York City Itinerary

Website: www.guggenheim.org

The Frick Collection

See world-class art by Vermeer, Renoir, and Rembrandt in a beautifully designed residence.

IMPORTANT: The Frick Collection is currently closed for a renovation project although it is planned to reopen late in 2024. The works of art were relocated to a temporary location, called the Frick Madison, which is in the Marcel Breuer-designed modernist building at 945 Madison Avenue. Learn more here.

Website: www.frick.org

Lunch

Where you choose to have lunch depends upon the art museum you visit. If you chose the MoMA, here are two recommendations:

Patsy’s Italian Restaurant: This family-owned restaurant has been in business since 1944. Frank Sinatra made this place famous and many other celebrities have dined here, including Ben Stiller, Tom Hanks, Oprah Winfrey, James Gandolfini, and many more. I recommend the Eggplant Parmesan (it was the best I ever had!).

The Black Tap: This restaurant serves craft burgers and beer but it’s famous for its over-the-top milkshakes topped with brownies, cookies, and slices of cake and pie (mentioned under Day 1 as a dessert destination near SoHo).

If you picked one of the other art museums, explore the area around the museum for lunch spots.

Central Park

Central Park is one of the most visited tourist attractions in the world. Therefore a visit to New York City would not be complete without at least a quick stroll through part of the park.

Central Park is much more than a tourist destination. For New Yorkers, this is a treasured green space, a spot to lie out in the sun, go for a run, and take the kids to the playground.

Spend part of the afternoon exploring Central Park. You can simply wander through it on your own two feet, rent bikes and cycle a lap or two through the entire park, or do something very touristy and go for a horse and carriage ride. There are numerous places to rent bikes just outside of the park. We have the best luck one block south of the park around 5th and 6th avenue. You can also rent bikes in advance here.

The Mall | 5 Day New York City Itinerary

Central Park in mid-April | 5 Day New York City Itinerary

Notable spots to visit in Central Park are the Imagine Mosaic at Strawberry Fields, Bow Bridge (one of the most photographed locations in the park), Belvedere Castle, Sheep Meadow, and The Mall.

Explore Midtown Manhattan

For the rest of the afternoon, stroll through midtown Manhattan. From Central Park, pop into The Plaza, one of the most famous hotels in the world. Then stroll down Fifth Avenue until you get to St. Patrick’s Cathedral.

Fifth Avenue | 5 Day New York City Itinerary

St. Patrick’s Cathedral | 5 Day New York City Itinerary

Top of the Rock Observation Deck or SUMMIT One Vanderbilt

Today, take your pick between two observation decks: Top of the Rock and SUMMIT One Vanderbilt. Of the two, SUMMIT One Vanderbilt is our favorite. You get one of the best views of Manhattan and it is a very unique experience, with the mirrored rooms and immersive art installations. Top of the Rock is also very nice, but it doesn’t beat the view from SUMMIT. For photos of both, check out our Guide to NYC’s Observation Decks.

If you choose Top of the Rock, the best time to visit it is now, since it is located on top of Rockefeller Center. If you choose SUMMIT One Vanderbilt, plan your visit for the end of the day, when you are near Grand Central Terminal. Time your visit an hour before sunset for the best experience.

From Top of the Rock, you get a great view of New York City from Midtown Manhattan. To the north you see Central Park, Harlem, and the Bronx. To the south, you not only get to see the Empire State Building, but you also get to see the towering skyscrapers of the financial district (and One World Trade Center) off in the distance.

View from Top of the Rock in February 2018, before One Vanderbilt was constructed. 

While in the area, you can also take a tour of Rockefeller Center and Radio City Music Hall. Just note, if you do choose to take a tour, you will have to skip most of the activities planned this afternoon.

Times Square

From Rockefeller Center, it’s just a five-minute walk to iconic, crowded, chaotic, touristy Times Square.

Times Square | 5 Day New York City Itinerary

This is one of the most famous intersections in the world. Every New Year’s Eve, thousands people gather to watch the ball drop, making this the most famous place in the world to welcome in the New Year. During the other 364 days of the year, Times Square is almost as crowded, as street performers put on shows and visitors from around the world gawk at the millions of lights that adorn the neon billboards.

It seems like Times Square is always changing. Every year, there are bigger and better billboards, new stores designed to draw visitors in, and crazier street performers on the streets. It is a crowded, overwhelming place and not everyone enjoys this experience. Take as long (or as little) as you like in this dazzling, gaudy place.

New York Public Library and Grand Central Station

There are just a few more spots to visit on this very busy afternoon. From Times Square, walk to Bryant Park and the New York Public Library. The library is free and it is worth a quick visit. It’s a beautiful building on the inside and has been featured in popular movies such as “Ghostbusters,” “The Day after Tomorrow,” and “Sex and the City.”

Rose Reading Room the the NYC Public Library

A few blocks from the library is Grand Central Terminal. This is the largest train station in the world, with 44 train platforms. The Main Concourse is a gorgeous spot to visit. Walk up the steps to the Apple Store and watch the show as hundreds of people crisscross the Main Concourse.

Grand Central Terminal | 5 Day New York City Itinerary

Inside of Grand Central Terminal is the Grand Central Market. This is a small market but it is a great place to put together a meal. With fresh fruits, pastas, cheese, and wine, you have the option to assemble a picnic dinner here.

SUMMIT One Vanderbilt

One Vanderbilt is the fourth tallest building in Manhattan. On the top three levels of One Vanderbilt is SUMMIT, New York City’s newest observation deck. The views are spectacular but SUMMIT One Vanderbilt takes the experience to a whole different level. On these three floors is a state-of-the-art, fully immersive experience with art installations, mirrored rooms, glass sky boxes, and a glass elevator. 

SUMMIT One Vanderbilt | 5 Day New York City Itinerary

Tickets start at $43 and a visit here typically lasts 2 hours. In my opinion, the best time to visit SUMMIT One Vanderbilt is an hour before sunset.

End the day with dinner and drinks. If you like the idea of Japanese food, consider going to Momosan Ramen & Sake, just a few blocks from Grand Central Terminal and One Vanderbilt.

New York City Itinerary: Day 3

The Statue of Liberty, Ellis Island, the Tenement Museum & a Food Tour

The Statue of Liberty and Ellis Island

If it’s your first time in New York, the Statue of Liberty is a must see. You can visit just the Statue of Liberty or you can visit the Statue of Liberty and Ellis Island together as a round trip excursion from Manhattan.

Statue of Liberty | 5 Day New York City Itinerary

At the Statue of Liberty, you can climb the base of the statue or go all of the way to the crown. Both of these options require advance tickets, and they do sell out, so make sure you book your tickets well in advance.

Ellis Island was an immigrant inspection station and approximately 12 million immigrants were processed here between 1905 and 1954.

Ellis Island | 5 Day New York City Itinerary

Liberty Island (the location of the Statue of Liberty) and Ellis Island are connected by ferry with Battery Park (on Manhattan).

The entire visit, from Battery Park to Liberty Island and Ellis Island, and then back to Battery Park, takes about 4 to 6 hours. You will take a ferry from Battery Park to Liberty Island. After seeing the Statue of Liberty, catch the next ferry to Ellis Island and tour this island. Then take a ferry back to Battery Park.

Cost: Tickets start at $25
Hours: Ferries depart from Battery Park from 9:30 am to 3:30 pm
Website: Book your tickets in advance on www.statuecruises.com

Tenement Museum

Now that you learned about what it was like to be an immigrant arriving in the United States, continue the experience with a visit to the Tenement Museum. Located on the Lower East Side, learn about what it was like to live as an immigrant between the 19th and 21st centuries.

Numerous tours are offered. Visit the Tenement Museum website for full details.

To get to the Tenement Museum from Battery Park, walk to the Broad Street station and take line J uptown four stations to Delancey St/Essex St (8 minutes).

Take a Food Tour in Manhattan

Little Italy and Chinatown are places that are frequently listed in guidebooks. For years, we loved spending an afternoon wandering through Chinatown or dining at a restaurant in Little Italy. However, in recent years, things have changed. Now, most of the restaurants in Little Italy are mediocre, overpriced restaurants that are well worth skipping. On our most recent visit to New York, Tim and I stopped into one of these restaurants for a drink and even the wine was mediocre.

Little Italy | 5 Day New York City Itinerary

If you are curious about Little Italy and Chinatown, they are still worth a quick visit. But you should know that there are much better places in New York for quality Italian and Chinese food.

A better way to spend the afternoon is to take a food tour in Manhattan. This 2-hour walking food tour of Hell’s Kitchen gets rave reviews. If you like the idea of combining a walking tour with a food tour of Greenwich Village, I recommend taking a look at this tour. Finally, on this 3-hour food tour on the Lower East Side you will sample German, Dutch, Italian, Chinese, and Jewish dishes and hear stories about the immigrants who settled here.

New York City Itinerary: Day 4

Brooklyn

Walking distance: 4 miles

Brooklyn is becoming one of New York City’s hot spots to visit. With historic neighborhoods, a fabulous food scene, and some of the best views of the Manhattan skyline, this is a great place to add to your New York City itinerary.

Since Brooklyn is so large, it’s impossible to visit all of it in just one day. With just one day you can visit the neighborhood of Williamsburg and the areas along the East River. Think of today as a mini food tour combined with some of the best views of Manhattan and the Brooklyn Bridge.

Dumbo (Down under the Manhattan Bridge Overpass)

Williamsburg, Brooklyn | 5 Day New York City Itinerary

Walking across the Brooklyn Bridge

The day starts in Williamsburg, a wonderful neighborhood with boutique shops, a variety of restaurants, and the Brooklyn Brewery. Then, take a ferry on the East River to Dumbo and the Brooklyn Bridge. From here, enjoy one of the best views of the Manhattan skyline, dine on the best pizza in the city, and end with a walk over the iconic Brooklyn Bridge.

Get the full details in our article: One Perfect Day in Brooklyn

New York City Itinerary: Day 5

Empire State Building, Chelsea Market, the High Line & Hudson Yards

Walking distance 3 miles (if you include the option to visit Greenwich Village)

Empire State Building

Start the day with a trip up the Empire State Building. Completed in 1931, this was the tallest building in the world for 40 years until the North Tower of the World Trade Center was completed in 1970. The Empire State Building has been featured in over 250 TV shows and movies and is listed as one of the Seven Wonders of the Modern World.

Looking north from the Empire State Building (June 2021).

Looking south from the Empire State Building.

If you don’t mind waking up early, you can watch the sunrise from the top of the Empire State Building. Tickets are limited to 100 visitors and need to be purchased in advance. It’s pricey, costing $100 per person, and tickets are only available for Friday and Saturday mornings.

Cost: standard tickets start at $44 for adults and $38 for children
Hours: Vary be season. Get updated hours on the official website.
Website: Get the full details on packages and VIP experiences on the official Empire State Building website.
Get Your Guide: You can also purchase your entrance tickets in advance through GetYourGuide.

Chelsea Market

From the Empire State Building, visit Chelsea Market for lunch.

The Chelsea Market is food paradise!! This is one of our favorite places in Manhattan for lunch. Inside of the market are numerous small restaurants selling food from around the world. Our favorite restaurants are Los Tacos No. 1, the Lobster Place, and Takumi Taco. There are also a number of boutique shops if you like to go shopping.

Chelsea Market | 5 Day New York City Itinerary

How to Get to Chelsea Market from the Empire State Building: From the Empire State Building, it is a 3-minute walk to the 34 St – Herald Square Subway Station. Take the D train (orange) towards Coney Island. At W 4 St – Washington Square, transfer to E train (blue) towards Jamaica Center. Exit at 14 St/8 Ave and walk one block to Chelsea Market. This takes 16 minutes. Or, take a taxi, Uber, or Lyft.

Optional: 9/11 Museum Workshop

One block away from Chelsea Market is the Ground Zero Museum Workshop. This museum documents what life was like for the workers and firefighters at Ground Zero during the recovery effort. Filled with artifacts and photographs, this is a great museum to visit if you want to learn more about what it was like to be at the World Trade Center site after the terrorist attack. This is one of the most underrated museums in New York City and well worth your time.

9/11 Museum Workshop | 5 Day New York City Itinerary

Website: Learn more about the museum here.

Optional: Greenwich Village

Spend an hour or two in Greenwich Village. Greenwich Village was the location of the 60’s counterculture movements and the modern LGBT movement. Now, the “bohemian days” are long gone, due to rising housing costs and gentrification of the neighborhood, but this is still a wonderful spot to visit.

To get the most out of your visit, this walking tour of Greenwich Village sounds amazing. Learn where Jimi Hendrix and Edgar Allen Poe hung out, where one of Bob Dylan’s album covers was photographed, and the rise of gay rights in New York City.

The High Line

Mid-afternoon, walk the High Line to Hudson Yards. This is a public park and elevated walking path that was built on a historic freight line.

The High Line | 5 Day New York City Itinerary

It’s free to visit and one of Manhattan’s prettiest walks. The High Line starts near the Whitney Museum, but you can also get onto the High Line from Chelsea Market.

It takes about 30 minutes to walk from Chelsea Market to Hudson Yards.

Hudson Yards, the Vessel, & the Edge

Spend the rest of the day in the ultra-modern Hudson Yards.

What was once a storage yard and jumble of train tracks has evolved into Manhattan’s newest ultra-modern neighborhood.

The trains and their tracks are still here, but this small city has been built on a state-of-the-art platform that is elevated above the railroad tracks. Glass-plated skyscrapers, a shopping mall, a performing arts theater, and two of Manhattan’s very popular attractions, the Vessel and the Edge, can all be found here.

The Vessel

Only the ground level of the Vessel can be visited. However, later in 2024, there are plans to reopen the upper levels.

The Vessel | 5 Day New York City Itinerary

The Edge

In 2020, The Edge joined the growing number of observation decks in Manhattan. Hovering 100 floors above the city streets, this sky deck offers jaw-dropping views over Manhattan. Adding to the thrill is the glass floor, where you can peer down to the city streets far below.

The Edge | 5 Day New York City Itinerary

The best time to visit the Edge is at sunset. These tickets sell out in advance, so make your reservations once you know your dates of travel. If you can’t get sunset tickets, you can arrive mid to late afternoon and stick around for sunset. I also recommend checking GetYourGuide, because they are an authorized ticket seller for Hudson Yards and they might have availability for your date and time.

There is also a new experience. Called City Climb, you wear a harness, climb up along the edge of the skyscraper, and view New York City from the highest observation deck in the city. This takes two hours and ends with a visit to the Edge. We did this in November 2021 and it is awesome! It’s definitely the most thrilling view of Manhattan. For more information and photos, click the link below to read our Guide to the Edge and City Climb.

Note: City Climb ends with a visit to the Edge sky deck. The City Climb experience takes 2 hours. If you book one of the last tours of the day, you can end with sunset views from the Edge.

Cost: Tickets start at $40 for the Edge. There is an additional $10 to $20 fee for sunset tickets. For City Climb, tickets start at $185.
Hours: 8 am to midnight
Getting Here: From the Vessel, enter The Shops at Hudson Yards, which sit right next to the Vessel. Take the elevator to the 4th floor and follow signs to the Edge.

If you want to have dinner in Hudson Yards, Peak restaurant at the Edge is pricey but the views of Manhattan are spectacular. For the best experience, make a reservation in advance and request a table with a view of the city skyline. We recently had a great lunch at Mercado Little Spain. Estiatorio Milos (Greek food) is one of our favorite restaurants in Manhattan.

For more suggestions of places to visit in Chelsea, read our article Best Things to Do in Chelsea & Hudson Yards.

More Ideas for How to Spend Your Time

Seeing a show on Broadway is a quintessential New York experience. You can book your tickets in advance, or buy them the same day through TKTS in Times Square. 

Watch a baseball game at Yankee Stadium, visit Luna Park at Coney Island, take a cruise of New York Harbor, fly over Manhattan in a helicopter, or even run in the New York City Marathon.

For a full list of things to do, check out our New York City Bucket List: 50 Best Things to Do in New York.

Using the Subway

To get around New York City, we recommend using the Subway. The New York City Subway is functional but it is dirty, smelly, and in great need of renovation work. It may not be pretty but it will get you where you need to go cheaply and efficiently.

I recommend downloading the NYC Subway app on your smartphone (it’s free!). This is the app I use to find routes between destinations.

I also recommend purchasing a 7 Day Unlimited Ride Metrocard. It costs $34 and you can ride the subway an unlimited number of times in seven days (there is not a 5 day unlimited ride Metrocard). It costs $3.25 per ride on the metro. If you ride the metro 11 or more times (which you will do on this itinerary) the card pays for itself.

Hotel Recommendations

For more recommendations, take a look at our article Where to Stay in New York City: Best Hotels and Neighborhoods for Your Budget. Get an overview of New York City’s most popular neighborhoods with recommendations on where to stay in each of them.

If you have any questions about how to spend 5 days in New York City or how to plan your New York City itinerary, comment below!

More Information about New York City

BEST OF NEW YORK CITY: For a list of the top experiences in New York City, read our article Best Things to Do in New York City.

NYC OBSERVATION DECKS: In our article Best Observation Decks in New York City, we rank all of the observation decks by price, height, and best view. We also have detailed guides on The Edge, SUMMIT One Vanderbilt, and One World Observatory.

CHELSEA & HUDSON YARDS: In our article Best Things to Do in Chelsea and Hudson Yards, learn about the best things to do in the area, with suggestions on where to eat and where to stay.

BROOKLYN: If you have plans to visit Brooklyn, read our article How to Spend One Day in Brooklyn.

NYC HOTELS: Need a place to stay? Check out our guide to the Best Hotels in New York City,organized by neighborhood.

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