New York Itinerary – 5 Days in New York City

Five days in New York City is the perfect amount of time to see all of the iconic NYC attractions and neighborhoods. Our 5 days in New York itinerary will help you plan an excellent vacation to the Big Apple blending the popular New York City sites with a few lesser-known destinations.

After reading on Forbes that New York City is looking forward to being back in business by July 1 (according to Mayor Bill de Blasio) it’s time to start planning a trip to the Big Apple. It’s back baby! After the year we’ve all had, I’m looking forward to taking my vaccinated self across the border when it opens to visit friends and see the sights. New York has a special place in our hearts and we’ve been sitting on this itinerary since our last trip just a few weeks before the pandemic hit. Check this website for updates, resources and restrictions in New York.

As out of towners, we always treat our New York City itinerary like we are seeing it for the first time. We go up the Empire State Building or Top of the Rock with each visit. We can’t get enough of that Manhattan skyline. But there is a lot more to the city and we’ve broken down what to do for first timers and people who have been to New York before but are looking for something new. Enjoy!

Our New York Itinerary

On our multiple trips to New York, we’ve used a New York Pass to make the most of our time and save money. If you plan on seeing a lot of attractions, this is a great investment to use on your New York itinerary as it gets you into tourist attractions with big savings. But only if you plan on seeing a lot of attractions. It doesn’t pay for itself if you only are planning on a couple of NYC attractions during your visit.

New York is huge and seeing it all in a short time can be overwhelming. We don’t want you crisscrossing around town by subway or taxi, so we start each morning in an area of the city and work our way around with as little transportation as possible.

5 Days in New York

If you only have five days in New York we’ve laid out this NYC itinerary to give you a chance to see most of the iconic sites in the first three days.

• Day 1: Statue of Liberty, Ellis Island, The Wall Street Bull, 911 Memorial,
• Day 2: Museum of Natural History, Central Park, The Metropolitan Museum, MOMA, Guggenheim, Broadway
• Day 3: Highline, The Vessel, Chelsae Market, MOMA, Radio City Music Hall Tour, Rockefeller Centre, Top of the Rock
• Day 4 – Grand Central Terminal, Bryant Park, Macy’s, Washington Square Park, SOHO, Little Italy
• Day 5 – Staten Island Ferry, Brooklyn Bridge, DUMBO, Empire State Building,

If you only have one day in New York City, we suggest keeping your New York itinerary to one area of Manhattan and revolving your itinerary around the must-see attractions on your list. But if you have five days in New York City, you’ll be able to enjoy at a more relaxing pace and see the best of the city in one shot!

Note: Some activities may be still affected by covid-19. Check with each attraction for opening hours and activities. Things are constantly changing as New York City moves into different stages of Covid so be sure to check before you go.

We’ve been to New York several times and each time we go, we fall in love with the city. If you follow our New York City itinerary, you’ll be able to see all the top New York attractions without feeling stressed out.

• If you are looking for where to stay in New York and wondering what the best neighborhood is for you, read our complete breakdown of New York City Hotels and Neighborhoods.
• If you want to stay near all the action you may want to check out this apartment rental to feel like a real New Yorker. It’s close to the Brooklyn Bridge, Financial District and more!

Day 1 – Statue of Liberty and Financial District

Statue of Liberty and Ellis Island, Wall Street, 9/11 Memorial Museum

A visit to New York is not complete without going to the Statue of Liberty. We put this first on our NYC itinerary because it starts in the south of Manhattan and it is a good idea to get there first thing in the morning.

Morning Day 1 New York Itinerary

Statue of Liberty National Monument

The Statue of Liberty is a great way to start your New York Itinerary. What better way than to see the New York Skyline from the ferry en route to this historic monument. Make your way to Castle Clinton in the Battery where you board the ferry to the island.

The first ferry leaves at 8:30 am and this is the best time to visit to make the most of your day. You can kill two birds with one stone seeing the Statue of Liberty as it includes a sightseeing cruise of the New York Skyline.

Taking the subway to Battery Park, we picked up our tickets and set off for a beautiful view of the NYC skyline to the Statue of Liberty.

Tickets include both the Statue of Liberty and Ellis Island, so depending on how much time you take to explore, it can take 5-6 hours. Ferry queues can be 30 minutes long and the ferry to the Statue of Liberty is about 15 minutes, so you have a lot of travel time.

Getting to the Statue of Liberty

• We took the Number 1 Red Line Subway from Manhattan hotel to the South Ferry Station near Battery Park.
• Take the 4 or 5 trains to Bowling Green.
• Take the R train to Whitehall Street.

Battery Park (The Battery)

When you finish up at the Statue of Liberty and Ellis Island, take a stroll through Battery Park as you make your way to the next stop on your New York itinerary.

It offers great views of the harbor where you just came from and this historic part of New York has several memorials, view points and a sea glass carousel paying homage to the old aquarium that was located at  Castle Clinton. (where you catch the ferries to the Statue of Liberty.)

Afternoon Day 1 – Wall Street and Financial District

If you want to really save time, you can grab a hot dog or pretzel on the Statue of Liberty ferry on your way back for lunch. Or pop into a diner on your way to the next stop on your NYC itinerary.

The Wall Street area of Manhattan is the perfect place to spend the afternoon of your first day in New York. From the Statue of Liberty, you can start walking North to see some of New York’s top attractions.

Charging Bull

Our first stop is the Charging Bull of Wall Street. Grab a photo before walking on to see Wall Street. Be aware, the lines are long for a picture with the charging bull. If you really want a picture with it, I’d suggest going before your statue of Liberty Tour at 6 or 7 am.

Wall Street

Wall Street is the heartbeat of the American economy and you can see the New York Stock Exchange, Federal Hall, and Trinity Church. Grab a coffee and stroll through the streets before heading off to your afternoon destination on your New York City Itinerary.

9/11 Memorial Plaza

I cannot stress enough how beautiful and important 9/11 Memorial Plaza museum is to visit. It shows the true spirit of New Yorkers as it commemorates those who were lost in the 9/11 attacks and honours the first responders and people of New York.

This museum is impressive enough from the outside with the two memorial pools built on the footprints of the North and South Towers of the World Trade Center.

The pools are a gentle reminder of the lives lost with waterfalls plunging 30 feet into a basin. The architect Michael Arad stated that the pools represent “absence made visible.” The water flows into the voids, they can never be filled.

9/11 Memorial Museum

Be sure to go inside the memorial (included with your CityPass) to see the exhibition honoring the lives lost. It is truly a moving display that is also hopeful and shows the strength of the city.

It is a must-stop on any New York Itinerary and even New Yorkers feel that this museum does justice to those impacted by this terrible tragedy.

Freedom Tower Observation Deck

There is nothing better than seeing New York City from above. For your first view of the New York City skyline go up New York’s highest observation deck.

This is an extra charge outside your ticket to the memorial museum but is included in your New York Pass.

Oculus

When you have finished in the museum, don’t miss going into the Oculus. This area of New York has been completely transformed with modern architecture and art displays from the New York Academy of Sciences.

The Oculus is a photographer’s dream. It is also the subway stop for the World Trade Centre. If you are moving on to another part of New York, you can hop on the train system here.

Even if you aren’t taking transit, you must go inside this 4-billion dollar design! It is stunning. The design of stark white steel ribs interlocking high above the ground represents doves flying from the hands of a child. It gives a sense of hope at the site of a tragedy.

Evening Day 1 – New York City Itinerary

It’s your first night in New York, so keep it simple and loose. You don’t want to have to run to a Broadway Show yet.

If you have the New York Pass, there are plenty of tours included in your pass. Here are a couple of good options near the Oculus.

• Take a Ghosts of Greenwich Village Tour starting at 8pm
• Take a Statue by night Circle Cruise

Check out a comedy show at the Comedy Cellar in Greenwich Village or if you want, it’s fun to wander the streets and look for a nightclub or bar to pop into and watch some live music.

We enjoy simply walking up 5th avenue toward midtown while taking in the busy vibe of the city.

Day 2 – Museums and Culture

American Museum of Natural History, Central Park, Museum Mile, The Metropolitan Museum, Broadway

Today is a day for getting your culture fix of New York City. With your New York City Pass in hand, it’s time to see a few of its iconic museums.

Morning Day 2 New York Itinerary

If you are looking for place to stay to explore the museums and culture of New York, check out this lovely vacation rental in the Upper West Side.

For hotels in this area, we stayed at the Hotel Beacon. It is well run and beautifully designed hotel, close to the subway lines in a very family-friendly area. Check out Availability and prices on TripAdvisor or Booking.com

American Museum of Natural History

We are going to start uptown at the Museum of Natural History. If you have kids, they’ll love this museum. Think of the movie A Night at the Museum with Ben Stiller.

This is the type of museum the Museum of Natural History is. You’ll see the lifelike displays of dinosaurs and wildlife taking you through all things nature on earth.

We didn’t spend too much time in this museum. But we saw enough to make it worth our while.

Central Park

Central Park is a mainstay of any visit to NYC. You aren’t far from the park once you leave the Museum of Natural History, so make your way to the park and take a tour.

You can explore on your own, but a tour will help you see the highlights quickly. So many movies have been filmed in Central Park, that a movie tour is a good option.

Central Park Bike Tours and rentals are free with the New York Pass. As well as other Central Park Walking tours like the Movie walking tour.

You can rent a bicycle to see the top Central Park sites like Bethesda Fountain, Belvedere Castle, and the Mall

We always make our way to the John Lennon Memorial. Strawberry Fields is located on the West Side of Central Park right across the street from where Lennon was shot while entering his apartment, the Dakota.

Lunch

This is a great time to pick up lunch from a food truck. They are line all along the streets of Central Park. We grabbed a hot dog and pop.

Afternoon Day 2 – New York City Itinerary

Museum Mile – The Guggenheim

After touring Central Park, make your way to the East Side and visit Museum Mile on Fifth Avenue. Your New York Pass will get you into most museums. We popped into the Guggenheim to see its iconic spiral ceiling designed by Frank Lloyd Wright. We didn’t feel the need to spend a lot of time here, but it is fun to go inside to see the design. And by having it included in our pass, we didn’t feel pressure to stay for long.

Metropolitan Museum Museum of Art

This was our favourite museum to visit in New York and the one we spent the most time in. We recommend spending the rest of your afternoon here. We gave it a couple of hours, but you could easily spend an entire day inside. When we go back to New York, it’s on our list to spend a full day here.

If you have a short time, here are a few things to see the highlights and then get on with your New York Itinerary

• Highlights Include:
  • Van Gough’s self-portrait
  • Dantes Inferno
  • Egyptian Display with Ancient Tombs
  • Recreation of the Sistine Chapel
  • Venus Italica

Evening Day 2 NYC Itinerary

Broadway

If you are in New York, make a point to see a Broadway show. This is a great time in your three day NYC itinerary to sit back and explore Broadway. Book tickets in advance to your favorite musical or play, but be sure to stroll around to search for its famous theatres that surround Times Square like the Richard Rogers, the Winter Garden and the New Amsterdam Theater.

Times Square at Night

When the show is over, go for a walk through Times Square to feel the energy of New York. Most New Yorkers hate Times Square, but we love it every time we visit the city. The square is surrounded by billboards and highrises. It’s filled with people and energy and it’s a fun stop on any New York City itinerary.

Day 3 – Iconic Views and Historic Places

The Vessel, The High Line, Chelsea Market, Times Square, Radio City Music Hall, Rockefeller Center, Empire State Building

Day 3 is going to be a great day on your New York City Itinerary. You are now about to see all of the top attractions and we are going to start our day by the water. Today is your day to put that New York Pass to good use. We are going to keep you out until the wee hours of the morning, so get ready to experience what it’s like in the city that never sleeps.

Morning Day 3 New York Itinerary

Planning on staying near the High Line? You may want to check out this apartment rental to feel like a local.

For hotels in Chelsea, check out Innside by Melia. It is one of the best hotels in the area. The rooms are spacious, efficient, modern, and well-appointed. Great staff and location make this a great choice. Check out Availability and prices on TripAdvisor or Booking.com

The Vessel

Hop in a yellow cab or take the subway to The Hudson Yards Shopping Center. Here is where you are going to book your time for the Vessel. The Vessel is New York’s newest art installation and it is an eye popping display.

The spiral staircase takes you up 250o steps for a view of the Hudson River and surrounding skyscrapers. It’s worth going inside, so don’t skip it! Get here early in the morning as slots fill up and you don’t want to be navigating through crowds.

If you haven’t booked a ticket in advance, you can do that now for free at the kiosk and set your time for the day. Or you can pay $10 to go inside anytime. If you want to book ahead of time (highly recommended, you can do so on their Website

The High Line

After you finish up at The Vessel, grab a coffee and take a stroll along the High Line. This is our favourite New York experience. This elevated park traces the route of an old train track for 2.3 km (1.5 miles). From here enjoy your morning coffee and take in the views of the New York City lofts, condos and skyscrapers making your way towards Chelsea Market.

Brunch at Chelsea Market

This historic New York attractions was home to Nabisco. It was the factory where Oreo Cookies were made. Mmm. There are countless eateries to choose from to fit any craving. So grab a bit here before moving on.

From Chelsea Market you have two choices, you can head back up to Times Square for the second half of our itinerary, or you can stay in the area if you have time to see

Afternoon Day 3 New York City Itinerary

MOMA

We have decided to head up to the Times Square area for the afternoon, and our first stop is the Museum of Modern Art (MOMA) is a great place to pop into. What I love about using a New York Pass is getting to pop in and out places without wasting money. Dave and I aren’t huge museum people, but when we’re in cities, we love to see the top attractions. And MOMA is a top attraction in New York. Museum lovers will spend hours in there. We spent about 45 minutes.

Before heading over to MOMA, stop in at the Radio City Music Hall box office to book your time for the Rockettes Tour. It took us several visits before booking this tour and when we finally did, we loved it!

Rockefeller Centre

A visit to New York wouldn’t be complete without going to the Rockefeller Centre. If you are in New York at Christmas, you must stop to see people skating on the outdoor ice rink and of course check out the Christmas Tree. But it is worth visiting any time of the year. It’s always abuzz with people.

It is here that you’ll be able to look for some of your favourite celebrities as it is home to NBC Studios. We always get a kick out of walking by the Tonight Show with Jimmy Fallon.

And if you want to recreate the scene from the movie Big where Tom Hanks plays the giant piano, you can pop into FAO Schwartz which has moved to Rockefeller Center.

Radio City Music Hall – Stage Door Tour

It took us several visits to New York to take a Rockettes tour, but when it was free with our pass, we gave it a shot and this was a lot of fun. Go back stage of Radio City Music Hall to see how the state of the art stage works, pop into the rehearsal hall and see the private quarters of Samuel “Roxy” Rothafel who wined and dined the greatest artists of the time including Walt Disney, Alfred Hitchcock, and Judy Garland.

Plus, you get to meet a Rockette as well! This tour is free with your New York Pass. but you need to book ahead of time at the box office. We booked our tour a couple of hours in advance at the box office.

Dinner

This is now a great time to grab a bite to eat before you begin your evening sightseeing. There are tons of restaurants around the area, so we aren’t to give a solid suggestion, but we enjoyed our time at the outdoor City Winery at in the North Plaza between 50th and 51st and Fifth and Sixth Aves.

Evening Day 3

Top of the Rock

Now that your belly is full, it’s time to see New York from above. The star attraction of the Rockefeller Center is the Top of the Rock and we suggest going in the evening to see the city lights.

Your New York Pass gives you access to the Observation Deck and we feel that this is the best view of the city looking at the Empire State Building. Going in the evening offers less crowds to deal with and this is the time when the city is absolutely beautiful.

Top of the Rock entrance is free with the New York Pass or you can get more information on visiting the Top of the Rock at their website. Open until 11pm (reduced hours for COVID)

You could end the third day of your itinerary here or you can find a club to see live music, comedy or head into Hells Kitchen for a late night snack.

You have now spent three days in New York. Congratulations, now head back to your hotel for a good rest, because there is plenty more to see.

Day 4 – Shopping and NYC Neighbourhoods

Morning Day 4 New York Itinerary

Today is a day to relax and pick up all the places you still want to see in New York. It was a late night last night, so you can relax and have breakfast at an authentic New York City diner. Today we are taking in the culture and heartbeat of New York.

Grand Central Terminal

Make your way to Grand Central Terminal, and take a moment to explore the largest train station in the world. Go inside up to the second level to watch the hustle and bustle of the daily New York City commuters.

And then, head down to the lower level to find the whispering gallery where the acoustics are so good, you can hear a whisper.

New York Public Library

After you’ve finished up in Grand Central, you can pop into the historic New York Public Library before heading to Bryant Park. If you are an architectural buff, you can take free tours every Monday to Saturday at 11.

Bryant Park

Continue your stroll through Manhattan to Bryant Park. This is year round gathering place with outdoor markets, el fresco dining, and even evening movie nights during the summer months.

At Christmas in New York, there’s a great outdoor market and be sure to rent a pair of skates and do some proper New York Christmas skating.

Macy’s at Herald Square

It’s your final day in New York, so pop into the historic Macy’s department store to pick up an NYC souvenir. It is Macy’s flagship store dating back to 1902.

Flatiron Building

It is now time to begin your own self-guided walking tour of New York, and as you walk the streets, your first stop will be the Flatiron Building.

This building is so iconic, it was established a National Historic Landmark in 1978. It is also a photographer’s dream and one of the quintessential buildings in New York. Depending on how long you took at the morning’s attractions, you may want to grab lunch in the neighborhood.

Washington Square Park

Moving our way down 5th Avenue, takes us to the picturesque Washington Square Park in Greenwich Village. This is where “Friends” took place and where the opening credits show the gang playing in the fountain. The Washington Square Arch is a popular meeting place in New York.

SOHO

SOHO (South of Houston Street) is a trendy neighborhood in Manhattan and is a great place to spend the afternoon. Go shopping in its many boutiques, pop into one of its art galleries and grab a pastry to tie you over until dinner.

• You can also book a SOHO, Little Italy, Chinatown Tour free with your New York Pass.

Little Italy and Chinatown

Make your way to the famous Mulberry Street to soak in the charm of Little Italy. Take in the Italian vibe and find a restaurant to have dinner. This historic district has changed a lot over the years, but it is still a fun place to visit to get a sense of that New York history.

There are great nightclubs and bars in the SOHO and Little Italy neighborhoods. so finish off your New York itinerary at a nightclub watching a band, a comedy show or going dancing. New York has something for everyone. The streets are always busy, and the best way to explore is to follow the crowds. If a bar looks busy, pop inside to see what’s going on!

Evening – Four Days in New York

Empire State Building at Night

Tonight you are going to experience the city that never sleeps and make your way to the Empire State Building. We have been to the Empire State Building a few times and the absolute best time is to go after 11pm. If you have enjoyed a dinner and a few cocktails in Little Italy or SOHO, end the evening here for and incredible view of the city lights.

The crowds are minimal, you don’t have to stand in line and you have the observation deck all to yourself. If you are going out to enjoy the nightlife, you can go late into the night. It doesn’t close until 2am!

Now that you’ve been out until the wee hours of the morning you have completed 4 days in New York. You’ve done more than most people now. Head back to your hotel and rest, because tomorrow is another big day as you complete your five days in New York itinerary with a bang.

Day 5

Staten Island Ferry, Brooklyn

If you are looking to stay outside of Manhattan in a quieter neighborhood, The William Vale in Brooklyn is a good choice. If you want the royal treatment this is the perfect place to stay. Close to the subway, this hotel is beautiful. With a rooftop pool, amazing restaurant and stunning rooms. Check our full breakdown of Brooklyn Hotels.

Morning Day 5 New York Itinerary

Start the last day of your New York City itinerary with a free view of Manhattan on the Staten Island Ferry. You can catch the ferry at Whitehall Terminal in Manhattan (just south of The Battery) and it is free to board. It is a 25 minute journey and offers great views of the New York City skyline and the Statue of Liberty. This is a great option if you don’t want to book a cruise or go to the Statue of Liberty on a tour. You can get your NYC Cruise and Lady Liberty views all at once! Check their website for more details.

When you get to Staten Island you will have to disembark and then get on another ferry. Ferries leave every 15 to 20 minutes. So you are free to stick around for a bit to explore, grab a coffee and see the NYC Skyline.

• If you want to spend some time on Staten Island, there are a few things to do here you can see the The Staten Island September 11th Memorial to commemorate the commuters who lost their lives in the September 11 attack.
• A popular thing to do here is to also shop at the Empire outlets for some brand name discount shopping.

A Slice of Brooklyn Pizza Tours

If you don’t want to take the Staten Island Ferry and instead want to make your way direction to Brooklyn (your day 5 destination) check out the Slice of Brooklyn Pizza Tours. If you want to get a sense of Brooklyn and the pizza culture of New York, this is a great tour.

We hopped on a bus and enjoyed sightseeing through Brooklyn while stopping at iconic pizza shops like Grimaldi’s in DUMBO and L&B Spumoni Gardens in Bensonhurst.  The tour let us sample, Neapolitan and Sicilian-style pizzas. Plus, we saw movie locations from some of the most iconic New York movie settings like Saturday Night Fever and Goodfellas.

If you have another day in New York, or if it is a second or third visit. Check out a few of these off the beaten path destinations on your own.

Walk Across the Brooklyn Bridge

When you make your way back to Manhattan, it’s time to make your way to Brooklyn. One of the most iconic things to do in New York is to walk across the Brooklyn Bridge. It is a 20 minute walk from the terminal to the Brooklyn Bridge and this is a perfect time to head over to Brooklyn for the best views of the New York City skyline and a chance to explore a new neighborhood.

It is a busy commuting hub and you’ll be sharing it with cyclists, and people out for a run as well as tourists and families. At 2km (1.2 miles) long, it’s an easy walk.

Brooklyn Bridge Park

Once you cross the Brooklyn Bridge, you’ll be in a fantastic borough of Brooklyn. This is the hot spot in the city.

If you are a photographer, Brooklyn Bridge Park at Pier 1 is the best spot to grab an iconic picture of the skyline. We went there with our friend Susan of The Insatiable Traveler (A native New Yorker) and it really is an epic view. After you’ve taken in the scene stroll East through the park along the waterfront towards DUMBO. Here you’ll pass Jane’s Carousel that you’ll recognize from so many movies set in New York.

DUMBO

Once you are in the DUMBO (Down Under the Manhattan Bridge Overpass) area, you’ll want to grab lunch. There are plenty of places to grab a bite, check out Cecconi’s and try to get a spot on the patio. While in DUMBO, stop under the Manhattan Bridge for yet another iconic view of New York.

Washington Street

You’ll recognize the view of the Manhattan Bridge from Washington Street from every New York City gangster film you’ve ever watched. This is that classic view from the Cobblestone Street that epitomizes the history and culture of New York City.

From here, it’s easy to get anywhere in New York, so hop on the subway and make your way back to your hotel to relax after your first day of your New York City Itinerary.

Afternoon Day 5

Make your way back to Manhattan and check off the last of your to do list. What have you missed seeing in New York so far? This is a choose your adventure afternoon.

Maybe you want to go back to Times Square to see the iconic billboards again. Or perhaps you want to go shopping at Bloomingdales.

Madison Square Gardens

If you can still put your New York Pass to use, book a tour of Madison Square Gardens. Go inside the home of the New York Knicks and NHL’s New York Rangers and feel the history that has pumped through its halls over the last 150 years.

The Met Cloisters

If you want to head way uptown, check out the Cloisters. The Cloisters is a part of the Metropolitan Museum of Art, but it is located in Northern Manhattan. It is a branch that is dedicated to medieval Europe. The lovely cloisters (a covered walk in a convent or monastery) reminded us of the monasteries we visited in Spain.Instagrammers love taking photos of this building.

Evening Day 5

Since you are uptown, instead of heading back to Manhattan, have dinner in Harlem and catch an evening of Jazz. The Apollo Theater is one of New York’s most famous venues. There’s amateur nights every Wednesday or you can book your tickets in advance If you can’t get into the Apollo, there are many jazz clubs to choose from. The Lonely Planet has a great round-up of clubs.

And that is our ultimate 5 day itinerary in New York City. You can easily mix and match or change days around. But this is the most comprehensive way we have explored by not having to get on the subway too much.

Getting Around New York

New York transit is so easy to use. It is fast, effeciant and affordable. It’s your best way to get around New York.

Uber, Lyft and the Yellow Cabs are also very affordable. As a Canadian, our credit card didn’t work in NYC taxis though, so have cash on hand.

We mention the New York Pass as it is exceptional for saving time and money, but we don’t recommend using the Hop on Hop Off bus included with the pass. It wastes time and is too slow. Just hop on the subway or hail a cab like the New Yorkers do.

If you are looking for where to stay in New York and wondering what the best neighborhood is for you, read our complete breakdown of New York City Hotels and Neighborhoods.