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How to Spend 5 Days in NYC: A Complete New York Itinerary

How to Spend 5 Days in NYC: A Complete New York Itinerary

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New York City is one of the most famous cities in the world, full of vivacious culture, rich history, world-class eateries, art, and so much more! As the “City That Never Sleeps”, you’ll have to jump on that schedule in order to see it all! 

This city has become iconic for a reason, I was amazed at how many famous things there were to see when we went for the first time. From the oldest bar in NYC to celebrity-filled neighborhoods to notable skyscrapers featured in films (I’m looking at you King Kong and the Empire State Building), you’ll never be bored here! 

It can be a little overwhelming to know where to start! So after our most recent visit, we have picked out the best things to do in New York City for a 5-day itinerary. This is just enough time to hit the main attractions, like the Chelsea Market, 9/11 Memorial, or the Statue of Liberty, and maybe take a food tour to try a few of the thousands of restaurants!

We will walk you through 5 days in New York City, from what bagel shop you should hit in the morning to finding the best NYC Passes to save money on attractions. There’s a lot to know, so don’t fret, just read on!

Don’t have time to read the full article? Five days is the perfect amount of time to take in some of NYC’s best sights! Save money and grab The New York Pass as your ticket to 100 attractions. Then don’t miss the Empire State Building Observation Deck, strolling around Central Park, picking up doughnuts at Chelsea Market, and taking in bucket list-worthy activities like a dinner cruise past the Statue of Liberty or a helicopter tour over Manhattan!

Table Of Contents
  1. 5-Day NYC Itinerary Overview
  2. Day 1 in New York City
  3. Day 2 in New York City
  4. Day 3 in New York City
  5. Day 4 in New York City
  6. Day 5 in New York City
  7. Know Before You Go
  8. Where to Stay in New York City
  9. Thanks for reading!
  10. Why We Book Tours with Viator

5-Day NYC Itinerary Overview

View out the front window of a helicopter tour in Manhattan, New York City
What a sight to see!
A damaged firetruck at the 911 Memorial and Museum
A damaged firetruck at the 911 Memorial and Museum

This 5-day New York City itinerary is all about seeing the top sights and getting to know the food, history, and culture of this iconic city. We’ve listed some of the top attractions, like visiting the 9/11 Memorial or the Empire State Building, and also some fun local New Yorker activities! You can visit Chelsea Market for some amazing food, hit a speakeasy, or hang out in Central Park – yes, locals actually hang out here!

This itinerary provides some breakfast, lunch, and dinner recommendations, but when it doesn’t you can explore on your own and eat along the way! New York has everything from world-famous restaurants to the best hole-in-the-wall joints. Who knows, you might even find the absolute best slice of New York-style pizza!

Related Read: One of the most popular day trips out of NYC is visiting Niagara Falls! You can easily take a tour to Niagara Falls from New York City!

Day 1 in New York City

Get a New York City bagel (breakfast)

Bailey eats a Bagel from Liberty Bagels in New York City
Liberty Bagels are famous!
The New Yorker Bagel from Liberty Bagels in New York City
This is known as the New Yorker!

There are a handful of staple foods that you have to try, and a New York City bagel is certainly one of them! It’s the perfect start to your 5 days in NYC.

Liberty Bagels is probably the most well-known for having the best bagels in the city, don’t ask a local as you might start an argument as they take “the best bagel” title very seriously, but take our word for it– they are good!

Their bagels are so special because they are kettle-boiled and the homemade cream cheese is to die for. There are locations on Broadway, Fifth Avenue, and Midtown, so no matter where you’re staying in New York, you’ll likely be walking distance to one of them!

You can go classic and get a plain bagel and cream cheese, but I recommend getting one of their sandwiches. I got the New Yorker that had roast beef stacked between an egg and hashbrown. Who knew a bagel sandwich could be so good!? 

Go up the Empire State Building

Views of New York City and the Hudson River as seen from the Empire State Building in NYC
The view from the Empire State Building Observation Deck!

Starting out day one with a bang is a must – so head up to the top of the Empire State Building! This is the most notable building along NYC’s skyline and is as famous as the Eiffel Tower or the Sydney Opera House

The Empire State Building is located in Midtown Manhattan and was completed in 1931. It was built in a “race to the sky” by the city’s property developers, but it won the race and held the title of the tallest building in the world for 40 years until the World Trade Center was completed in 1971. The Empire State Building stands 1,250 feet (380 meters) tall and is a sight to behold.

Because of its staggering height and sleek design, the Empire State Building became an instant icon. It has almost become a symbol for New York itself and has been featured in many movies, like King Kong, Elf, Sleepless in Seattle, and so many more! 

There are two observation decks at the Empire State Building where you can get some of the best views of the city! The main observation deck is on the 86th floor, or you can pay extra to go up to the top deck on the 102nd floor. I personally found the 86th-floor view to be awesome so you don’t need to go up higher, but it is quieter on the 102nd floor if you want to escape the crowds! You can purchase tickets to the 86th floor for $48 USD.

You can also purchase a sunset ticket for $11 USD more, as this is the most beautiful time to visit the observation deck! There is even a “skip the line” ticket available for $92 USD. The observation decks are open 365 days a year from 8 am to 2 am, so it can even be a fun late-night shenanigan!

You can’t go to New York and not see the Empire State Building – that’s just crazy!

Visit the New York Public Library (quick stop)

Bailey walks down some stairs at the New York Public Library
Inside the New York Public Library.
Bailey stands out the front of the New York Public Library in New York City
The front of the Library.

Making a quick stop at the New York Public Library is another prominent sight. Plus, it’s one of the best free activities in NYC since there’s no cost to visit! The library is a notable stop because of its gorgeous architecture, dating back to its earliest creation in 1897 and finally opening in 1911. Its Beaux-Arts architectural style has inspired several important libraries around the world. 

You’ll probably recognize the New York Public Library as soon as you see it. It has been in many TV shows and movies, such as Breakfast at Tiffany’s, Tobey Maguire’s Spider-Man, 13 Going On 30, and Sex and the City. The two large lions out front are also rather famous. They are named Patience and Fortitude and they are great for taking selfies with!

The first room you’ll enter is Astor Hall and it’s stunning with its marble arches and dramatic staircases. This room is so beautiful, it is frequently rented out for weddings! You’ll also visit the Rose Reading Room, which has 52-foot ceilings with gorgeous murals. If you have kids along, check out the Children’s Center to see the stuffed animals that inspired the Winnie the Pooh books!

You’ll want about one hour to explore the library. It is located in Midtown, near Times Square, and is quite easy to find. It is an absolute must-see if you are a book or movie lover! 

Admire St. Patrick’s Cathedral (quick stop)

the outside of St Patricks Cathedral in New York
It’s a stunning building!
Inside the St. Patrick's Cathedral in New York City
Inside St. Patrick’s Cathedral

Just a 10-minute walk down the road is St. Patrick’s Cathedral. This is a seriously impressive neo-Gothic cathedral located just opposite Rockefeller Center. It is captivating from the street with its dramatic steeples, but you can also go inside and see the ornate beauty up close. The cross beams almost make it look like a ribcage, which totally goes with the neo-Gothic vibe!

It is free to enter and you really don’t need to spend much time here, but it’s along your route and centrally located to other notable attractions like the Museum of Modern Art, Grand Central Station, and the giant Nintendo Store. It’s definitely a beautiful stop on day one of your 5 day itinerary in New York City! 

Angelo’s Coal Oven Pizzeria (lunch)

Angelo's Coal Oven Pizzeria in New York City
Photo credit: Angelo’s Coal Oven Pizzeria

It’s time to continue the food tour of New York (let’s be honest, that’s really what exploring a city is about!). I probably don’t have to tell you that New York is famous for its pizza. The debate in the U.S. is always New York-style thin crust or Chicago-style deep dish. Well, here you can try one of them in their hometown at Angelo’s Coal Oven Pizzeria

New York’s pizza scene goes waaaaaaay back and Angelo’s Coal Oven Pizzeria has been family-run for four generations from its humble beginnings by an immigrant family in the 1930s. As the founder and namesake would lament, there are few real thin-crust pizza joints left in the city. So you know you’re getting the best of the best!

The flavor is incredible and you can tell each recipe is made with the details in mind. From the dough, sauce, cheese, and fresh toppings, Angelo’s has the best pizza in NYC. It’s a great lunch stop, but try not to overeat because you still have the afternoon ahead of you! Angelo’s is located only two blocks from Central Park and is open from 11:30 am to 10 pm on weekdays and 11 pm on weekends. 

Explore Central Park (afternoon)

Beautiful pond in Central Park, New York City
A fountain in Central Park

Central Park is a quintessential New York location. Not only is it a nice break from the bustling city, but it is simply gorgeous in its design! This has also been featured in countless movies, TV shows, and books. There is even a tribute to the late Beatles member, John Lennon here. So the culture runs deep at Central Park. 

Central Park was first opened to the public in 1858 and continued to be developed over the next 15 years. Now, you’ll find 1.3 square miles (3.4 square kilometers) of green space that covers multiple different sections, located right in the middle of Manhattan. Central Park is loved by locals, as even they need an escape from the concrete jungle! 

Sheep Meadow is the perfect place to relax in the sun and grassy fields and you can also check out the historic carousel, a giant ice skating rink (open October to April), and the Belvedere Castle. New York really goes out on everything and it is a beautiful sight to see. 

While you can definitely just walk around the park and get a good feel for it, there are a few other ways to experience it too. I’ve even compiled a list of the best Central Park tours to make things easy for you.

My favorite option is to rent a bicycle and pedal through Central Park, that way you can really cover some ground and see more! You can rent a bike for the entire day for just $26 USD, I recommend booking it in advance if this is something you’re interested in.

Or if you feel like getting a little cheesy and romantic, you can take a horse-drawn carriage ride through Central Park for $195 USD per carriage (up to 4 people)! This is definitely a memorable way to see this legendary park, and when else will you get this experience!? 

See a Broadway show (night)

Bailey at the Book or Moorman Theater on Broadway in New York City
Bailey at the Book of Mormon on Broadway in New York City
The cast of Book of Moorman say thankyou after an awesome show on Broadway in New York City
The cast of Book of Mormon say thank you after an awesome show on Broadway in New York City

Going to a Broadway show is an experience to remember, and honestly is super impressive even if you’re not a musical fan, like Daniel! But, when in New York right? So we booked tickets to the Book of Mormon and even he had a really good time. It was hilarious (it has the same writers as South Park) and the set design/logistics are mind-blowing– a great first-time Broadway experience!

There are so many iconic shows that run long-term on Broadway or others that rotate through. The Lion King has been running since 1997 and hit the nail on the head regarding shows. The music is incredible, as well as the costumes and props, there’s a reason it’s the third longest-running Broadway production! You can get tickets to The Lion King starting at $145 USD for the rear mezzanine level, and prices go up and fluctuate due to availability or seat preference. 

If you’re particularly interested in the history and production of Broadway, you can take this walking tour of the Broadway Theaters and Times Square, led by a real Broadway performer! It gives the inside scoop of what it’s like to work on Broadway, as well as the history and happenings of the theater district. Tours are $39 USD and depart at 4 pm, and they last for about 2 hours, ending right in time to catch a show!

Related Read: After your trip, hop over the border and check out Toronto! There are some great tours in Toronto that give you the whole Canadian experience, which is quite different from NYC!

Day 2 in New York City

Visit the Chelsea Market (late breakfast/morning)

Bailey poses for a photo inside the Chelsea Market in New York City
Inside Chelsea Market
Doughnuts at Doughnuttery at the Chelsea Market on a food tour in NYC
Be sure to stop at the Doughnuttery!

Starting your second day of 5-days in New York itinerary with a late breakfast is essential after a late-night Broadway show. The Chelsea Market is yet another NYC staple; really it’s a staple in the worldwide food scene! This giant food hall has over 40 stalls that offer cuisine from all over the world. If you want variety, this is your place to go! 

Chelsea Market was originally built in the 1890s as the Nabisco Factory (the birthplace of Oreos). Over time, it has changed hands quite a bit and was eventually built into a food hall in the 1990s as the neighborhood moved from an industrial area to more of a trendy neighborhood. Today, Chelsea Market receives over 6 million visitors annually, and I can see why! The scope of food was incredible, and nearly everything we tasted was fantastic – it’s a true NYC icon.

But, with more than 40 different incredible food options, it can be hard to figure out where to start. To maximize our tasting abilities, we decided to take a food tour of Chelsea Market, and let me tell you it was one of our best decisions in NYC! This food tour will certainly let you try a lot of dishes, and the tour guide will select the best and biggest variety of restaurants so you get the whole feel. We also got to skip the lines, which helped us save time to eat more food! 

We really loved the mini donuts at the Doughnuttery, as well as the tacos at Los Tacos No. 1. They really are the #1 tacos in NYC in our opinion! But the real stand out was the thin-slice pizza at Filaga Pizzeria. Owned by Sicilian natives, they really know how to make the perfect NYC slice! 

I can’t recommend taking this food tour of Chelsea Market enough! It can be booked in advance for $84 USD. 

Walk the High Line

Wide angle shot of The High Line traveling avoce NYC streets
The High Line Trail!

You’ll want to go for a nice walk after all that food at Chelsea Market! Luckily, the High Line is located right next to the market, and if you took the food tour we mentioned above, it includes a stop at the High Line. 

The High Line is a park built on old freight railway tracks that were set to be demolished at one point, but the community lobbied to convert it to a park area. So today we have an elevated park with 1.45 miles (2.3 kilometers) of uninterrupted walking trails each way. In New York City, the concrete jungle, having a park with lots of walking space is a luxury! Because it is elevated on old train lines, you get beautiful city views along the way.

The trail extends from Gansevoort Street and West 34th Street, near Hudson Yards. There are also stairs and elevator access to the High Line, so it’s accessible to those in wheelchairs too. Along the High Line, you’ll find public parks with playgrounds, art installations, exercise classes, and places to eat and drink. We bought some coffee and it was a wonderful little stroll!

We were way too full from our Chelsea Market food tour to try anything more, but the Hearth on the High Line is a super cute wine bar overlooking the Hudson River that’s worth trying. Malai Ice Cream also looked delicious, as it serves up South Asian ice cream, just another example of New York’s diverse and incredible food scene!

Take in the views from The Edge NYC

Bailey leans against the glass corner at Edge NYC
The Edge!
View of New York City and the Empire State Building from The Edge NYC
You can see the Empire State Building from up here!

What better way to see the city than from 100 stories up? The Edge NYC is only a 20-minute walk from Chelsea Market, so you can simply enjoy a walk along the High Line and make your way to the 30 Hudson Yards skyscraper, where the Edge NYC observation deck sits.

NYC has a few observation decks that show different viewpoints of the city. The Edge is unique because you get a perfect view of the Empire State Building! It is 1,100 feet (335 meters) tall, making it the highest observation deck not only in New York City but in the entire Western Hemisphere. The deck actually sticks out off the side of the building, so you are suspended over the city and really get incredible views if you can keep the nerves down!

The Edge is also equipped with a glass floor, so you can see how high up you really are, and the safety barrier leans outward. They actually encourage visitors to lean on the barrier – so I totally took advantage of that. It feels like you’re flying over the city! There are even two bars at the top, indoor and outdoor, so any time of year you can enjoy a glass of bubbles and a view! 

You can reserve your tickets to the Edge in advance on Viator for $41.37 USD. You might notice this is a few dollars more than the posted price of buying in person, but they don’t include the tax in the initial price, so in the end you’ll be saving about $2 USD by booking on Viator! Plus you’ll already have your tickets and don’t have to waste time standing in line. 

The Edge is also included in the New York Pass and Go City Explorer Pass packages, if you choose to purchase one of NYC’s great attraction passes.

Visit New York City’s oldest pub (afternoon)

Four beers on a table at McSorley's Old Ale House in New York City
It’s an old-school pub!
Daniel poses for a photo at McSorley's Old Ale House in New York City
Cheers!

One of the reasons we love NYC is because there is so much history all along the streets! Being such an old and iconic city, there are some true hidden gems you can visit, like McSorley’s Old Ale House!

This is the oldest pub in NYC that’s been open since 1854. It survived prohibition, both World Wars, the Great Depression, and even the COVID-19 pandemic, so it’s quite the legendary stop.

McSorley’s was opened by an Irish immigrant, John McSorley, and is filled with memorabilia from its patrons over the years. Abraham Lincoln is among the notable visitors, and there is even an original “wanted” poster for John Wilks Booth after Lincoln’s assassination. Henry Houdini also made a stop here, and you can find a pair of his handcuffs on the rafters. Women weren’t allowed to drink at McSorley’s until 1970, and a ladies’ restroom wasn’t even built until the 1980s! 

It has a long-standing history, to say the least!

McSorley’s only serves two things: light or dark beer. Don’t hum and haw on this decision either or else they won’t give you the time of day – just like a true Irish bar in New York! Beers are only $5.50 USD but hey only serve double-fisted rounds, so you have to buy two beers at once (okay twist my arm!). This is still a super cheap price for beer in New York!

Go for dinner in Little Italy (dinner) 

People eat dinner in Little Italy New York City
It’s such a trendy area!
Biley enjoys a meal at L'Amore Restaurant in little Italy New York City
L’Amore!

I can’t think of a better way to finish off the day than heading to Little Italy for some delicious Italian dinner. Little Italy has that same slow and romantic charm as you’d expect visiting Italy itself, which is the perfect end to a busy day of exploring!

I recommend spending a bit of time wandering the streets, taking in the atmosphere and delicious smells from all of the restaurants and bakeries around. There are many specialty shops here, so if you enjoy cooking you can pick up some authentic Italian ingredients to take home.

If you walk down Mulberry Street you’ll find some of the LISA Project murals, which is a nonprofit group dedicated to bringing a diverse group of artists to Lower Manhattan. You’ll see a lot of beautiful and creative murals – I am always so impressed by people’s artistic abilities!

We decided to stop for dinner at L’Amore Ristorante, which was a great pick! Although there are so many delicious restaurants in Little Italy, you really can’t go wrong. We loved the charming and romantic vibe of L’Amore, and the food was just as satisfying! 

If you’re up for a second food tour in one day, you can check out this food tour to find the yummiest restaurants in Little Italy! It also includes a stop in Chinatown for some more tastings. They take you to locally-owned family businesses so you get an authentic feel, and can support the little guys. The tour is $70 USD and is a great way to dive into Little Italy!

Day 3 in New York City

Breakfast at Johny’s Luncheonette (breakfast)

If you’re looking for a classic diner experience, Johny’s Luncheonette is the go-to place in NYC! It is small and has limited seating, so it has a fast pace (similar to New York as a whole) but you shouldn’t have to wait long for a table. This family-owned business has been open for over 30 years, and the owner, Johny, is an icon in the neighborhood. Johny’s Luncheonette was even listed as one of the top 10 brunch spots in NYC by Manhattan Magazine, so don’t skip out on this stop!

You can expect big plates of fluffy pancakes, eggs cooked to perfection, and the smell of greasy bacon everywhere. This is one of those diners where your coffee cup is never empty because the waitress is constantly coming by to top it off! Johnny’s Luncheonette is open every day of the week from 8 am to 2 pm, so you can enjoy breakfast or lunch here. 

There are diners all over the city, but few are as good as Johnny’s! Maybe it’s the food, or the welcoming, family atmosphere, but whatever it is – it works!

Walk around Greenwich Village

Washington Square Arch in Greenwich Village New York City
Washington Square Arch in Greenwich Village New York City

Greenwich Village, also known as simply “the Village” is one of the most well-known neighborhoods in all of New York City. You could easily spend a few days exploring all of the nooks and crannies of the Village, but since you only have 5 days in NYC, an afternoon will have to suffice!

The Village first came on the map in the 1960s as the hub of counterculture full of beatniks and artists. Today, it follows its historic roots by being the birthplace of the modern LGBT movement and is a very active community. It has been featured in the TV show Friends and was home to Bob Dylan and Jimi Hendrix! It is a huge hub for arts and culture, and you’ll always find something unique in the Village. 

While here, you can explore the most popular Off-Broadway theater, Cherry Lane Theatre, or many of the other iconic theaters in the neighborhood, as there are a lot! However, once you make your way to MacDougal Street, you’ve reached the pinnacle of Greenwich Village! This street is lined with tons of restaurants and dive bars, including Caffe Reggio, which was part of The Godfather movie.

If you explore the Village in the evening, be sure to stop at the Comedy Cellar to see up-and-coming comedians perform 15-minute sets, making for a hilarious night out.

If you’re interested in diving into the celebrity-filled history of the Village (as there’s a lot!) and you love experiencing a city through food as we do, this Greenwich Village Walking Tour is the best way to do it all! Your local guide will take you all around the Village, giving an in-depth history of the stars who have walked these streets, and stopping at the best restaurants along the way! It is $95 USD for a three-hour tour, which for how much food and information you’ll consume, it’s not a bad deal!

Get a New York slice at John’s of Bleecker Street (in Greenwich Village for lunch)

Bailey eats a New York Slice on a food tour at the Chelsea Market
You’ve got to try a New York slice!
Daniel eats a slice of pizza on a food tour in New York City
Yum!

For your lunch stop on day 3 of your 5 days in New York, John’s of Bleecker Street is an absolute must-visit! This is a famous pizzeria dating back to 1929 and is known all over the city for having some of the best pizzas in New York. This coal-brick-fired pizza has a super thin crust that is crispy and tasty. 

The secret to NYC pizza, I’ve learned, is that simplicity is key! Just a few simple ingredients that are fired to perfection are all you need. John’s of Bleecker Street is definitely a popular spot, but it moves quickly so even if there’s a line, it’s worth the wait!

Bleecker Street is another famous part of the Village that you must check out! Here you’ll find vintage boutiques with some designer brand hidden gems. Like many parts of New York City, Bleecker Street has been mentioned in many books, movies, and TV shows, but most notably in the Marvel Cinematic Universe. The address of the New York Sanctum is 177A Bleecker Street, which has been part of six Marvel movies, plus the original comic series. 

You’ll find a lot of personality in this part of the city, so definitely make Bleecker Street a stop! 

Relax

By now, you’ll probably want some downtime! Three straight days of exploring can be exhausting, and you still have a lot of New York to see! It’s okay to take some time off, go back to your hotel, and relax. 

Plus, our next stop is a little more fancy, so you’ll need some time to refresh at your hotel so you’re ready to go for dinner!

Bateaux New York Premier Dinner Cruise (dinner)

Daniel and Bailey with the Brooklyn bridge on a dinner cruise in NYC
The Brooklyn Bridge!
Bailey enjoys her dinner with the Statue of Liberty in the background during the Bateaux New York Premier Dinner Cruise in New York City
Our main course with Lady Liberty!

After spending a few days exploring New York City, it’s time to see it from a new perspective – on a dinner cruise along the Hudson River! This was easily my favorite thing we did in New York City as it was a fun fancy night out, gave incredible views of the city, and the food was so good I still think about it today!

Although there are many dinner cruises you can take in NYC, we went on the Bateaux New York Premier Dinner Cruise. I’ve taken many dinner cruises over the years, and this one was the absolute best!

Over three hours, we sailed in an all-glass boat so the views were incredible the entire time – even though it happened to be a rainy evening for us! It turned out to be one of the best rainy day activities in NYC and the up-close look at the Statue of Liberty as the main course is served was my favorite part. As the city began to light up, the skyline was more beautiful than I can describe. 

On top of the views, we also had a delicious three-course meal which, no joke, was the best meal we had in New York – and we ate a lot! There are some amazing chefs in New York City, and they brought the best of the best for this dinner cruise. Plus, there was live music on board which just added to the ambience for a spectacular evening. 

Prices for this dinner cruise range from $200 – $300 USD per person depending on the time of day and how far in advance you book. You might be thinking, is the Bateaux Dinner Cruise worth it? And I can confidently say “YES!”, it was a memorable and tasty experience that any traveler (or local) would enjoy.

Be sure to book this dinner cruise in advance so you can get the lowest price possible, and make sure you don’t miss out!

Why We Book Tours with Viator

Viator is a trusted online booking system for tours around the world! We almost always book our tours using Viator for a couple of reasons:

  • Free cancellation on most tours – Most of the tours on Viator allow you to cancel and get a full refund up to 24 hours in advance. This is handy in case plans change, or if booking an outdoor activity, the weather forecast is looking grim.
  • Reserve now and pay later – You can secure your spot on some of the most popular tours well in advance and not pay until closer to the day of the tour.
  • Pay in your chosen currency – Avoid costly international transaction fees by choosing to pay in your home currency.
  • Peace of mind – When booking with tour operators you find in person on the street or in small booking offices, you are often promised one thing and given another. This online platform holds tour operators accountable with a written description of inclusions as well as the opportunity for customers to leave reviews.

Check out the Viator website here! Or, for more info, read our detailed review about Viator here.

Day 4 in New York City

Visit the 9/11 Memorial and Museum (morning)

Bailey walks through the 911 Memorial and Museum in New York City
The steel beams that collapsed at the 9/11 Museum.
Flowers lay on the 911 Memorial in New York City
The 9/11 Memorial

A visit to New York City isn’t complete without paying homage to the 9/11 Memorial. We don’t need to explain how earth-shattering an event the attack on New York’s Twin Towers was to the city, albeit the entire world. So visiting the 9/11 Memorial and Museum is a very moving experience, and an important piece of the New York City itinerary to get an entire perspective of the city. 

The memorial is made of two very large pools that sit where each of the Twin Towers once stood. The names of the victims are carved into the sides of the pools, which shows you just how many people lost their lives in this event. It is quite moving to experience the scope of this tragedy. 

The memorial is free to enter, but to visit the 9/11 Museum, you’ll need to purchase tickets in advance. I highly recommend visiting the museum, because as impactful as seeing the memorial is, there is so much more you can learn and take away from visiting the museum. There are artifacts from the victims, rubble from the buildings, media reports, and first-hand accounts of the disaster. 

The museum has timed entry slots, and while you can stay as long as you want, you will need to arrive at your scheduled time. We spent about two hours here, plus the time checking out the memorial. Tickets to enter the museum are offered every 30 minutes and are $33 USD.

Visiting the 9/11 Memorial and Museum is also part of the New York CityPASS®, the New York Pass, or Go City’s Explorer Pass, in which case your entrance fees are covered!

Go on a helicopter flight over the city (morning/lunch)

Bailey with the Statue of Liberty and New York City in the background on a helicopter ride
Me with the Statue of Liberty!

By now, you’ve had some pretty epic views of New York City. From the top of skyscrapers, from the water on a cruise, and from the hustle and bustle of street level, but what about an aerial view? Imagine flying over one of the world’s most iconic cities like you’re a slow pan at the start of a romantic comedy movie. A helicopter flight over New York City was one of the most epic tours I’ve ever taken – and even though it’s short, it’s 100% worth it!

We took this 15-minute helicopter flight, although it felt much longer. Our pilot was so great at taking us to see the main attractions of NYC such as the Statue of Liberty, the Empire State Building, the Brooklyn Bridge, and the whole sprawling city below! Plus, riding in a helicopter was a thrilling experience, to say the least.

While this is a bit of an expensive activity at $229 USD per person, we can wholeheartedly say that it was an incredible experience and worth every penny. There are plenty of other Manhattan helicopter flights, such as this 25-30 minute Empire Helicopter Flight, to see even more epic views! And if money is no object, helicopter rides also make for some of the best private tours in NYC!

Regardless of which you choose, it will be an amazing addition to your 5-Day NYC itinerary.

See the charging Bull of Wall Street (quick stop)

The Charging Bull of Wall Street, New York City
The Charging Bull of Wall Street, New York City

You’ve had quite an eventful day so far, so this next stop is a quick, but essential addition to your docket. Head to the Financial District and see the Charging Bull statue, and while you’re here you can check out Wall Street, as that’s pretty iconic too!

The Charging Bull statue represents a “bull market”, which is a period of time of rising investment prices. The big-shot investors who work on Wall Street love the bull market, so the statue is somewhat of a symbol of good fortune.

In 1989, the statue was placed in front of the New York Stock Exchange illegally by artist Arturo Di Modica. There was a stark downturn in the market after the Black Monday market crash in 1987, and the artist wanted to send some encouragement! He dropped the statue at night, eluding police, only to have it moved in the morning to Bowling Green, where it still stands today. 

Walk the Brooklyn Bridge (afternoon)

Views of the river and bridge in NYC from the One World Observatory
The Brooklyn Bridge!
bailey walks along the Brooklyn Bridge in New York City
Walking across the bridge is a must-do!

New York is a famous city – what can we say? So our next activity is yet another “must-see-super-iconic” stop … the Brooklyn Bridge! It’s one of the world’s most recognizable bridges, featured in countless movies and photographs. Plus, walking the Brooklyn Bridge is free, which is hard to come by in New York!

The Brooklyn Bridge is 1.1 miles (1.8 kilometers) long, so while it isn’t terribly long, I would plan to add some extra time to check out the views, stop by the vendor stands, and enjoy the stroll! The walkway can be a bit crowded, in fact, 30,000 pedestrians cross the bridge every day! I recommend going earlier in the day if possible, as it can get hot by mid-day if you’re visiting New York City in the summer, and even more crowded as the day goes on. 

The main draw of visiting the bridge is the views! You can see almost the whole skyline, and the bridge itself is also quite stunning with its stone arches. It connects Lower Manhattan to Brooklyn Heights and was completed in 1883. 

If you’re coming from the Charging Bull as listed above, you will reach the Brooklyn Bridge in about 17 minutes. However, if you’re coming from midtown, it’s over an hour’s walk, so you can simply take the subway and get off at Chambers St. Station or Brooklyn Bridge-City Hall Station, which will spit you out steps from the entrance to the bridge. You can either walk the entire length of the bridge if you want to check out Brooklyn, or walk halfway and turn around to stay in Manhattan!

Go to a Speakeasy (night)

Daniel rings the phone at Please Don't Tell Speakeasy in New York City to gain entry
The pay phone to get into the bar called Please Don’t Tell!
Bailey enjoys a cocktail at Please Don't Tell Speakeasy in New York City
Cheers!

Step back in time by hitting a speakeasy at night! New York has had a long history of speakeasies since the Prohibition Era of 1919 shut down all legal sales of alcohol. Because of this new law, organized crime groups began opening hidden bars all over the city – no one was going to tell them they couldn’t drink! 

Even after Prohibition ended in 1933, the speakeasies remained in business. Today, visiting these hidden bars is certainly a trendy thing to do because they are so unique! New York is teeming with speakeasies, so it becomes a bit of a scavenger hunt to find them, and in true New York fashion, each one is rather eccentric and has its own vibe. 

Our favorite speakeasy is Please Don’t Tell, and since it’s officially on Google, I don’t think it’s much of a secret anymore, but it’s still fun to find. It’s hidden behind a hotdog restaurant and you have to go into the telephone booth in the back and dial 1 to enter. Inside, you’ll find gorgeous decor and delicious (and overpriced) cocktails – but it’s all about the experience! Be sure to make reservations in advance as it’s a very popular cocktail spot!

We also enjoyed The Woo Woo near Times Square, which has that seedy 1980s vibe. To get a full look at New York’s speakeasy scene, consider taking this speakeasy tour! Not only does it give you a detailed history of the underground liquor scene in New York, but it also gets you into some amazing speakeasies that you’d normally need a reservation for or have a hard time finding by yourself! The tour is $35 USD, but you do have to pay for your own drinks. 

Related Read: Taking a day trip to Washington D.C. is a great way to maximize your time touring the USA! We recommend taking a boat cruise on the Potomac River to see some of the iconic landmarks.

Day 5 in New York City

Statue of Liberty and Ellis Island Cruise (Morning)

New York City skyline with the Statue of Liberty on a scenic flight in NYC
Take a boat to Ellis Island and then get up close to Lady Liberty herself!

A true staple of New York City, and the United States itself, the Statue of Liberty stands proud on Liberty Island in the New York Harbor. Lady Liberty was a gift from France to celebrate 100 years of independence and the close relationship between the two nations. It was completed in 1886 and was strategically placed facing Southeast to welcome ships coming into the harbor.

Ellis Island is not too far off of the Statue of Liberty, and the location where millions of immigrants were processed upon arriving to New York. Ellis Island has quite a tangled history, from quarantine and families being separated, to new beginnings and long-awaited dreams for many other immigrants. The station was closed in 1954 and is now a memorial and museum. 

The Statue of Liberty and Ellis Island are often thought of together because the iconic statue was the first thing immigrants would see once they reached the United States, making it even more symbolic! 

Visiting both the Statue of Liberty and Ellis Island are absolute NYC bucket-list items. It’s easiest to visit them on a tour, like this one, that includes the ferry ride, entrance to both museums, and guide the whole time! Having a guide throughout exploring these historic places is so valuable because there is a ton of history that I wouldn’t have known without it! 

We especially liked this tour because it offers different tour lengths and departure times, so you can choose the option that works best for your itinerary. Tours are offered for 30 minutes, 2 hours, and 4 hours, but really the 4-hour tour is the best option! It feels way less rushed and gives you the big picture of these two historic sites. You can reserve the 4-hour guided tour of the Statue of Liberty and Ellis Island for $79 USD per person – book it online or check out the other options here!

Food tour in New York City (day)

Daniel at a hot dog stand in New York City
Try some street food!
Bailey with her Japanese Taco on our food tour inside the Chelsea Market on our guided food tour
Have you ever tried a Japanese taco before?

By now, you’ve probably picked up on the fact that New York City has an epic food scene. Arguably the most food-centric city, it is a culmination of flavors from all over the world. It might feel like there is no way you can begin to scratch the surface of the food culture during your 5 days in New York City, but I have the perfect tool to help: a food tour! A food tour in NYC is my favorite way to try an array of dishes and learn about its diverse culture in the yummiest way possible. 

And since this is your last day in New York, you can choose which part of the city you want to explore. Whether you missed a neighborhood or had a favorite one in particular and want to return, each of these tours is a little different, so choose the one that best suits you!

The Original Chinatown and Little Italy Food Fest

This Chinatown and Little Italy food tour visits two of the biggest immigrant neighborhoods in the city, which means delicious local food! Over 3 hours, your guide will take you to the best off-the-beaten-path restaurants to sample an array of dishes from gourmet to local eateries. You’ll start in Chinatown to sample various types of dumplings, pastries, jasmine green tea, and roasted duck. Little Italy will bring a whole different flavor with Italian olives, cheeses, pasta and marinara, and a cannoli paired with wine!

While the food is obviously the star of the show on these tours, the guide also does a great job of explaining the history of each neighborhood and how it’s grown and established itself as such an important part of New York’s culture. It’s a whole experience, the food, the culture, the neighborhoods – it’s all very NYC! This tour can be reserved for $125 USD, and trust me, you’ll leave here stuffed with some of the best food in the city!

A chef puts sauce on a pizza in Little Ital in NYC on a food tour
Yum!

Greenwich Village Walking and Food Tasting Tour 

The Village is also home to a slew of amazing restaurants, some might even say this is where to go if you’re looking for the best restaurants in the city! With a star-studded history, there are a lot of iconic places you can explore. 

This 3-hour food tour takes you to seven different eateries, so you better come hungry for this one! Start with falafel and then move on to Artichoke Basille’s Pizza, Pommes Frites, and then more pizza at Bleecker Street, which you might have stopped at already! 

You’ll take a quick food break and visit the building that was the facade shot for the apartment in the TV show, Friends, and Washington Square Park, which is another legendary New York park. You’ll also pass by the Stonewall Inn, a historical gay bar that started riots in 1969 to launch the gay rights movement. It’s a rather historic location!

The food parade continues at Faicco’s Italian Specialties for all sorts of tasty treats and finishes with cupcakes at Molly’s Cupcakes. It’s truly the perfect food tour! This tour is $95 USD and can be reserved online here!

New York Walking Food Tour With Secret Food Tours

Finally, for a slightly cheaper option, there is this New York Walking Food Tour with the highly-rated company Secret Food Tours. It’s a 3-hour tour that lets you choose whether you want to explore Chinatown and Little Italy or the Village, for only $85 USD per adult. So you can experience the same charm and flavors as the other tours, at a slightly lower price!

If you select the Chinatown and Little Italy option, you can expect to dine on dumplings, mozzarella, and handmade pizza. You’ll also get to dive into the history and culture of these neighborhoods!

The Village option is a true New York experience as you discover hidden gem eateries. Try classic NYC items like bagels, donuts, and pizza while you roam the beautiful streets of the Village! Either option will leave you full and happy, an excellent last-day activity! You can reserve this tour online here.

Visit Times Square (night)

Times Square in New York City at night
It’s such a cool place!
Crowds of people in Times Square in New York City
Times Square!

It’s your last night in New York City, so you better believe we saved the best for last – Times Square! Visiting Times Square is mind-blowing any time you visit, but it’s especially vibrant at night. There are hundreds of giant screens and lights surrounding it, it’s loud, chaotic, and energetic. It is iconically New York City, and I know I’ve said that about nearly everything on this list – but this is really it!

You can certainly have a lively experience by simply visiting Times Square and walking around, but you can also check out a few tour options to dive further into it. This nighttime bus tour shows just how the City That Never Sleeps comes to life after the sun goes down. It stops at many places along the way, but Times Square is by far the standout. If you’d rather take a walking tour, this small-group theater district tour focuses on Broadway, which surrounds the Times Square area. 

These tours are another opportunity to deep dive into the heartbeat of New York and get immersed in this vibrant city. Times Square really is like the cherry on top of your 5 Days in New York City!

Know Before You Go

Bailey looks through the Binoculars on the 86th floor of the Empire State building viewpoint
The Empire State Building Observation deck is included in the New York CityPASS®
A man inside the 911 museum looks at a steal beam that fell during the World Trade center terrorist attack
And so is the 9/11 Memorial and Museum

What are the New York Passes you can buy?

NYC Passes are a great option if you’re planning on doing some major sightseeing while visiting New York City. They even work well alongside sightseeing tours of NYC because not all tours cover entry into the attractions. With NYC Passes, you’ll essentially pay one flat fee for the pass and have admission to various sites covered. It actually ends up saving you almost 50% of sightseeing costs, which is fantastic as traveling in New York can get quite expensive!

There are a few different passes to choose from, so let me break them down.

The New York CityPASS® covers entrance to 5 attractions, which is perfect if you are planning on hitting one sight every day on your 5 day NYC itinerary. It already includes the Empire State Building Observation Deck and the American Museum of Natural History, and then you’ll select three more attractions from a pre-set list. This pass is valid for 9 days and is $138 USD, which for 5 days of sightseeing is a pretty good price! 

The New York Pass covers over 100 attractions and has prices tailored for how many days you’ll be using it. This is my top pick, as you can choose a 5-day option for $319 USD or plan to do all of your sightseeing in 3 or 4 days if you want to save a few dollars. The New York Pass has the most extensive list of attractions and gives you a lot of flexibility as you plan your 5 days in NYC. 

The New York City Explorer Pass by Go City allows entry for between 2-10 attractions, depending on which tier you choose. This is great if you have a handful of “must-sees” or enjoy tours, as there are a lot to choose from with this option. Prices start at $79 USD for 2 attractions and go all the way up to $264 USD for 10 attractions, depending on how much you want to see! The Explorer Pass by Go City covers a lot of sights, so check out what they offer before you decide on which pass to purchase!

Can you explore New York City without a car?

taxis parked on a busy street in New York City
Taxi is one of the most popular ways to get around for both locals and tourists!

Yes, this is actually the best way to explore New York City. You can use public transportation and walk to all of the main sights. The subway system is used by travelers and locals alike, just add some extra time into your itinerary to figure the system out. You can download the NYC Subway App and get a 7-Day Unlimited Ride Metrocard for $34 USD, and trust me, you’ll be using that a lot! 

Most of the time, you can take the subway close to whatever attraction you’re going to see, then walk a few blocks to find it. Uber and taxis are also an option if you don’t want to take the subway.

Is it safe to visit New York City?

Overall, New York is a safe city to explore. As with any major city, use caution at night, don’t carry valuables or large amounts of cash on you, and use your smart-traveler senses. If an area feels sketchy– it’s probably best you get out! But for the most part, New York is safer to visit than many movies and TV shows like to depict it – so don’t stress and enjoy your NYC trip!

Where to Stay in New York City

TBA Times Square Hotel Room
Our room at Delta Hotels by Marriott New York Times Square– classic, clean, and comfy!

New York City is huge – there is just no other way to put it! Even Manhattan (the area you’ll want to base yourself in) is a lot bigger than you think. That’s why choosing the right hotel in the right location is so important during your stay in New York.

Below, we’ve simplified it all for you by choosing a couple of the very best hotels available in the city. All three of these options have ideal locations close to attractions and the subway system. They all have amazing reviews, too, so just choose the one in your budget category and you’ll be ready to pack your bags!

Motto by Hilton – $$$

Motto by Hilton is a gorgeous hotel located in the Chelsea neighborhood only 600 meters from the Flatiron Building. The hotel features modern decor that has “speakeasy vibes.” In fact, they have a beautiful bar onsite that looks like the perfect place to sip an Old Fashioned. There are a variety of rooms on offer including some that are a little more budget-friendly, and some that are pure luxury with city views!

Prices start from about $400 USD per night plus tax. You can check prices and availability for Motto by Hilton online here!

Delta Hotels by Marriott New York Times Square – $$

Delta Hotels by Marriott New York Times Square is where we stayed the last time we visited New York, and honestly, we loved it! This hotel is the perfect combination of comfort and value for money. It was clean, modern, and our room had all of the amenities we needed for an enjoyable stay (air conditioning, k-cup coffee maker, steamer, large shower, big windows, etc). Plus, the location is ideal – it’s only a couple blocks from Times Square!

Prices do range, but they do go as low as $200 USD per night plus tax depending on the time of year and day of the week. You can check prices and book online here!

Nap York Central Park Sleep Station – $

For those traveling on a tight budget, Nap York is a budget hostel that’s an ideal choice. Although affordable, this property is immaculate and offers a ton of amenities for a great stay including air conditioning and a shared kitchen. The rooms are modern and the location is about as central as it gets! This property only offers dorm rooms, but they are affordable at as little as $100 USD per night.

You can check prices and book Nap York online on either Booking.com or Hostelworld.

Related Read: If you’re looking for more city guides, check out our 4 days in Vancouver (like a local) if you’re ready to explore another epic North American city!

Thanks for reading!

Daniel and Bailey take a selfie on the Edge NYC with the Empire State Building in the background
Thanks for reading!

It looks like you have a busy 5 days in New York City ahead of you! We followed pretty much this same itinerary while visiting NYC and had a blast! It’s hard to take as big of a city as New York and fit it into 5 days, but we think this hits the highlights.

I hope you found this blog helpful as you plan an epic trip to the Big Apple! If you’re looking for more travel inspiration, be sure to check out all of our USA blogs, as well as our Canada blogs! We are experts on North American travel, so you can use these resources to plan a trip you won’t soon forget. Here are some of my favorites below!

How to Spend Four Days in New York City – An Ideal 4-Day Itinerary

5 BEST Bike Tours in Toronto

12 Things to KNOW Before Visiting the Hockey Hall of Fame

The BEST Christmas Tours in New York City to Truly Capture the Christmas Spirit!