New York Itinerary: What to Do and See in 5 Days in NYC

Last Updated: 5/25/2023 | May 25th, 2023

First settled by the Dutch as “New Amsterdam” in 1624, the city came under English control in 1664. It was a major trading center thanks to its location at the mouth of the Hudson River. After the American Revolution, New York became the seat of America’s power and government, officially becoming the nation’s capital in 1789 when George Washington was sworn in.

While it’s no longer the nation’s capital (it moved to Philadelphia the following year and then to Washington, DC in 1800), NYC is still the beating heart of the country.

Home to around 10 million people, NYC has tons of things to see and do. You can barely scratch the surface on a typical four- or five-day visit. (But, then again, I don’t think even a four-month trip would be enough to see NYC! The city is constantly changing too much.)

In short, New York is impossible to “see” in one visit. This city is home to thousands of restaurants, hundreds of museums, attractions, plays, and quirky things to do. You just have to resign yourself to that fact, unless you move here (and maybe not even then), you’re only going to see a fraction of what you hope to see. It takes a while to get around town.

So, as a traveler, how do you visit NYC? What are the best things to see and do here? What is the best itinerary for NYC? How do you make the most of your time here?

There are ways to make the most of the limited time travelers have in New York. You need at least three days to really see the main highlights (though a “quick hits” tour could be done in a two-day NYC itinerary). However, I suggest 4-5 days to see the main sights without rushing too much.

Since I’ve written a guidebook to this city, lived there for over five years, have run tours there, and explored as much as I could in pursuit of knowing the best things to do in NYC, I want to share the best itinerary for New York City. This suggested itinerary can help you organize your trip and ensure you make the most of your visit — all while saving you money in the process.

NOTE: If you do everything on this itinerary, you’re going to be very, very busy. Don’t view this itinerary as a manual but more like a list of suggestions. If you want to pack it in, you can do it. However, don’t rush. Meander. The itinerary here just groups things together to give you a sense of how days can be optimized, but go at your own pace.

So, without further ado, here is my suggested New York itinerary:

 

New York City Itinerary: Day 1

Take a Walking Tour

Start your trip off with a walking tour. The city is home to dozens of walking tour companies (many of them free) offering tours in every niche possible. History, food, booze, TV/film — if you like it, chances are there is a tour revolving around it. Walking tours offer a unique look at the city that never sleeps from a local guide who can answer any and all of your questions. I always take my friends on at least one when they visit.

Some of my favorite walking tours and walking tour companies include:

• Take Walks
• Free Tours by Foot
• Bowery Boys Walks
• Speakeasy Drinks and Prohibition History Tour
• Gangsters and Ghosts Walking Tour
• Graffiti and Street Art Walking Tour

And for more suggestions, check out this list of my favorite NYC walking tours.

See the Statue of Liberty/Ellis Island

Though the line for the ferry from Battery Park is long, if you get there early, you can avoid most of it. (Come late and you’ll have to wait a few hours.) The Statue of Liberty is spectacular to see up close (she’s as big as you imagine), but the real highlight of this combo is Ellis Island. This is where you can learn about the immigrant experience and get a sense of the people who helped build NYC (you’ll even find my family’s name inscribed on the wall). There’s such a great sense of history there that you can’t help but be impressed.

Here’s a review of my experience taking a tour of the Statue and Ellis Island.

Tip: If the line’s too long and you don’t want to wait, take the free Staten Island ferry for photos of the statue and harbor instead. You won’t get up close but it’s faster and cheaper.

Battery Park, +1 212 363-3200, nps.gov/stli/index.htm. Open daily 9am-5pm. There is no admission fee for the island but the ferry ticket costs $24 USD.

Explore Battery Park
Located on the southern tip of Manhattan, this park is where the Dutch built Fort Amsterdam in 1625 to defend their settlement. The British took the area over in 1664 and eventually renamed it Fort George. While the fort was mostly destroyed during the American Revolution (1775-1783), the battery was expanded after the war’s end. You can wander around the fort and then stroll through the surrounding park to take in the beautiful waterfront views of the harbor, the Statue of Liberty, and Ellis Island.

There are also over 20 monuments and plaques in the park, covering everything from the Revolutionary War and the War of 1812 to immigration and much more.

Visit Wall Street

Take a photo with the famous charging bull statue (which was created in 1989) and then walk to Wall Street and see where all those bankers continually destroy the economy. There’s heavy security in the area, but you can sit and watch people whiz in and out of buildings on their way to cause some other financial disaster.

If you want to learn about historic market crashes and take a deep dive into what makes a financial crisis occur, check out the Financial Crisis Tour. Recommended by the BBC and the New York Times, it’s led by Wall Street insiders and will give you first-hand knowledge of what it’s like working on Wall Street.

See Federal Hall
One of the most overlooked museums in the city sits across the street from the NY Stock Exchange (NYSE). Federal Hall, built in 1700, is where George Washington took his oath of office (you can see the Bible he was sworn in on). It was the site of the US Customs House in the late 1700s and the first capitol building of the US.

Though the original façade was rebuilt, it’s one of my favorite attractions in the area. I especially love the old vaults. I highly recommend you visit!

26 Wall Street, Financial District, Lower Manhattan, +1 212 825 6990, nps.gov/feha. Admission is free. Open Monday-Friday, 10am-5pm.

Tour the Museum of American Finance

Down the street from NYSE and Federal Hall is the Museum of American Finance. Housed in a historic bank building on Wall Street, it has permanent exhibits on the financial markets, money, banking, entrepreneurship, and Alexander Hamilton (the founder of the US financial system). If you want to understand the workings of what happens on Wall Street, this is a perfect place to start.

Financial District, Lower Manhattan, +1 212 908 4110, moaf.org. Currently closed for relocation.

See Trinity Church

Built in 1698, the original Trinity Church was a small parish church constructed by the Church of England. When the British seized New York after George Washington’s retreat, it was used as a British base of operations.

The original church was destroyed in the Great Fire of 1776, a massive blaze that wiped out upwards of 25% of the city (the Americans blamed the British for starting the fire, while the British blamed the revolutionaries). The new building, facing Wall Street, was consecrated in 1790.

After the Revolutionary War, George Washington and Alexander Hamilton regularly worshiped here. The graveyard dates back to the 1700s and has many famous Americans there, including Hamilton and his wife Elizabeth, Francis Lewis (signatory on the Declaration of Independence), John Alsop (Continental Congress delegate), Albert Gallatin (founder of NYU), and Horatio Gates (Continental Army general). The church was expanded in 1839 into its current form.

74 Trinity Place, Financial District, Lower Manhattan, +1 212 602 0800, trinitywallstreet.org. Open daily from 8:30am–6pm.

Visit the World Trade Center & 9/11 Memorial and Museum

On September 11th, 2001, almost 3,000 people were killed in a series of terrorist attacks in NYC and elsewhere. Visit the somber memorial (which is free) and then take in the view from the new “Freedom Tower.” On the elevator up, you can see pictures of the historical development of the city and how it’s changed over the years.

To get a deeper understanding of 9/11 and the events that unfolded, visit the museum. It’s home to moving exhibits that illuminate the scope and significance of the tragedy.

180 Greenwich Street, Financial District, Lower Manhattan, +1 212 266 5211, 911memorial.org. Memorial open daily from 8am-8pm. The museum is open Wednesday-Monday, 9am-7pm. The memorial is free to visit; skip-the-line museum entry is $19.40 USD. Free entry Mondays from 3:30pm-5pm (tickets must be booked online).

DINNER OPTION: Eat at Ellen’s Stardust Diner
Since 1987, this diner is home to an incredible waitstaff of singers and dancers. Between tours and musical performances, actors and actresses wait tables at Ellen’s, where they belt out songs as they serve you slightly pricey, very American diner food (think shakes, burgers, and lasagna) in uniforms from the 1950s. It’s incredibly cheesy, which makes it incredibly fun!

1650 Broadway, Times Square, +1 212 956 5151, ellensstardustdiner.com. Open daily, 7am-midnight. There’s usually a line so be sure to plan ahead!

New York City Itinerary: Day 2

See City Hall

New York’s City Hall is a great piece of historic architecture and has a beautiful little park that’s filled with office workers during lunch (as well as a circular tablet about the site’s history). To learn about the building’s history, art, and architecture, take one of the tours. This way, you’ll be able to see the landmarked rotunda, city council chamber, Governor’s Room, and the City Hall Portrait Collection.

City Hall Park. nyc.gov/site/designcommission/public-programs/tours/city-hall.page. Pre-reserved tours are typically offered for groups (10–20 people) on Tuesdays at 10:30am and for individuals on Thursdays at 10am. There are also first-come, first-served tours on Wednesdays at 12pm and Thursdays at 10am.

Walk the Brooklyn Bridge

Right near City Hall, the Brooklyn Bridge offers an easy 25-minute walk into Brooklyn and the waterfront park on the other side. Stopping to take photos and meandering along the way will make the walk about 40 minutes. Opened in 1883, it was the first fixed bridge to span the East River (it was also the longest suspension bridge in the world at the time). You get a lot of wonderful views of downtown as you make your way across (and especially from the park).

I enjoy doing this walk at night when downtown Manhattan is all lit up. Otherwise, come early to beat the crowds.

Relax in Prospect Park

Once you get out of Manhattan, you can explore Brooklyn’s version of Central Park, which spans almost 600 acres. Inside the park you’ll find winding paths and bike lanes (there are bike rentals in the park or you can grab a bike from CitiBike, NYC’s bike share program), a rink for ice skating in the winter and rollerblading in the summer, a serene lake for boating, and the Smorgasburg food festival every Sunday.

While you’re here, don’t miss the Brooklyn Botanical Gardens (especially known for its magnificent cherry blossoms in the spring) and the Brooklyn Museum. Spend the afternoon discovering its vast collection of both historical and contemporary art and artifacts (there are over 1.5 million items in its collection). It has art exhibitions highlighting ancient Egypt, medieval Europe, colonial USA, and more.

200 Eastern Pkwy, +1 718 638 5000, brooklynmuseum.org. Open Wednesday-Sunday, 11am-6pm. Tickets are $16 USD.

Wander Rockefeller Center
This area is always filled with hustle and bustle. Wander around Rockefeller Center to see where they film The Today Show, shop, snack, and take the elevator to the Top of the Rock for another bird’s-eye view of the city, which I personally think is better than the Empire State Building, since from the top of here you can get that building in your picture too.

30 Rockefeller Plaza, +1 212 698 2000, topoftherocknyc.com. Open daily from 9am-11pm. Admission is $40 USD to visit the Top of the Rock observation deck.

Tour Radio City Music Hall

Is there a more American theater than Radio City Music Hall? A huge entertainment venue, this timeless testament to entertainment has captivated visitors since the 1930s (at the time, it was the largest auditorium in the world). It’s the home of the precision dance company The Rockettes, who have been performing here since 1932. It’s also been the venue for all kinds of award shows, including the Tonys and the Grammys.

1260 6th Avenue, +1 212 465 6080, msg.com/venue-tours/radio-city-music-hall. Open and giving one-hour tours daily from 10:30am-2pm. Admission is $33 USD.

Play tourist at Times Square

No matter when you go to Times Square, it will be packed with people (usually other tourists). There are pedestrian areas where you can sit and hang out. If you aren’t shopping or eating or seeing a show, there isn’t much to do in the area (and no New Yorker hangs out there), but it’s still a fabulous place to people-watch for a few minutes from the top of the red steps of the TKTS kiosk. Try to come at night when it’s all lit up. That’s when it looks the best.
 

New York City Itinerary: Day 3

Stroll around Central Park

The perfect way to relax in the city and leave the crowds behind is to spend the day in Central Park. It’s free, there are lots of paths to walk (or run), bike lanes, lakes to row in, and a zoo. Since the park covers over 150 square blocks, it’s easy to spend hours wandering around.

During the summer months, there are often free concerts and theater productions (line up early for tickets to Shakespeare in the Park). From the late spring to the early fall, there are free guided walks run by the parks service on Saturdays at 11am. I’m a big fan of laying out in Sheep’s Meadow on a hot, sunny day with a book, some food, and a bottle of wine.

Several excellent museums can be found in or on the edges of Central Park too (see below).

Visit the The Metropolitan Museum of Art

The Met is one of the biggest museums in the world, and if you only see one museum in New York, I recommend this one. It has a wide array of art, historical artifacts, photographs, and other exhibits. I like its expansive Impressionist and Greek exhibits. It’s chaotic and filled with people, especially on the weekend, but since it is so big, you can usually find some quiet spots away from the crowds. Budget at least a half-day here as a few hours won’t do this place justice.

If you’re short on time, Take Walks offers a Met Express Tour where an expert guide will take you to the absolute highlights and give you deeper insights into the pieces you’re seeing so you can make the most of your experience. It’s just two-hours long too.

1000 5th Avenue, Central Park, Upper East Side, +1 212 535 7710, metmuseum.org. Open Sunday–Tuesday from 10am–5pm, Fridays and Saturdays from 10am-9pm. Admission is $30 USD (includes same-day entrance to the Cloisters).

Visit the American Museum of Natural History

Made even more famous by the Night at the Museum movies, this museum also requires a lot of time. The exhibits on nature, human history, and marine life are interesting and detailed, so I wouldn’t try to rush your visit. My favorite is the one on the origin of humans. Learning about how we came to be is fascinating. Also, don’t skip the section on space (because space is awesome) at the Hayden Planetarium, which is run by Neil deGrasse Tyson. They have really detailed exhibitions of the origin of the universe.

Central Park W. at 79th Street, Upper West Side, +1 212 769 5100, amnh.org. Open daily from 10am-5:30pm. Admission is $28 USD (special exhibitions not included).

Take in the Museum of the City of New York
This museum can tell you everything you ever wanted to know about New York City. Architecture, parks, streets, as well as its people, and culture — it’s all covered! There are multiple rooms that highlight various time periods in NYC history featuring interviews, maps, interactive exhibits, profiles of historical figures, and various artifacts. It’s the best history museum in the city. There’s a cool exhibit here where you can create the future NYC, Sim City style. It’s great for kids!

1220 Fifth Avenue at 103rd St., +1 212-534-1672, mcny.org. Open Thursdays from 10am-9pm and Friday-Monday from 10am-5pm. Admission is $20 USD.

See a Broadway Show

You can’t go to New York City, the theater capital of the world, without seeing a show. Make sure you squeeze in an evening show somewhere while you are here! Current highlights and favorites include:

• The Lion King
• Wicked
• Aladdin
• Chicago
• Hamilton

Ticket prices vary greatly by show. However, you can find discounted tickets at the TKTS offices around the city (Times Square, South Street Seaport, and downtown Brooklyn) for shows that day. They also have an app where you can see what they offer too.
 

New York City Itinerary: Day 4

Visit the Cloisters

Few people make it up to the Cloisters (it’s all the way up near 204th Street), a branch of the Met devoted to medieval Europe. It took me years to finally see it, and I kicked myself for waiting so long. It was built with Rockefeller money from parts of five European abbeys between 1934 and 1939. They even stipulated that the land across the river would forever remain undeveloped so the view would be unspoiled.

The building and its stunning cloistered garden are very, very peaceful and beautiful. It’s one of the best things to do in the city. There are free tours each day that explain the history of the museum and the paintings and exhibits.

99 Margaret Corbin Drive, Fort Tryon Park, +1 212 923 3700, metmuseum.org/visit/visit-the-cloisters. Open Thursday-Tuesday from 10am-5pm. Closed Wednesday. Admission is $30 USD and includes same-day entry to The Met.

Visit the Museum of Modern Art (MoMA)
Head over to the MoMA for lots of beautiful (and weird) modern art and some vivid impressionist art. Personally, I don’t “get” modern art. I mean, how is a shovel on a wall art?

While I’m not a fan, this museum does have Van Gogh’s Starry Night as well as other post-impressionist art so I can’t hate it completely. If you love modern and contemporary art, this (I’m told) is one of the best in the world.

18 W. 54th Street, Midtown, +1 212 708 9400, moma.org. Open daily from 10:30am-5:30pm (7pm on Saturdays). Admission including skip-the-line access is $25 USD. The MoMA’s Sculpture Garden is free of charge to the public daily from 9:30am–10:15am.

Wander the Guggenheim Museum

This museum is home to a renowned collection of impressionist, post-impressionist, early modern, and contemporary art. The cylindrical museum (designed by Frank Lloyd Wright) is considered one of the 20th century’s most important architectural designs. It’s one of my favorite buildings (and museums) in the city.

1071 5th Avenue, Upper East Side, +1 212 423 3500, guggenheim.org. Open Sunday-Monday, Wednesday-Friday from 11am-6pm (Saturdays until 8pm). Admission is $25 USD. Pay what-you-wish is available on Saturdays from 6pm-8pm.

See the Frick Collection
This collection features paintings by major European artists (lots of Dutch masters here) as well as 18th-century French furniture and Oriental rugs. You have to really love Dutch artists to want to spend time here (I do) but be sure to visit their website in advance because they host a lot of wonderful temporary exhibits featuring famous works of art.

1 East 70th Street, +1 212-288-0700, frick.org. Open Thursday-Sunday from 10am-6pm. Admission is $22 USD. Thursdays from 4pm-6pm is pay-what-you-wish admission.
 

New York City Itinerary: Day 5

Walk the High Line & Whitney Museum

The High Line is a converted train track that is now an urban walking park that stretches between 34th Street and the Meatpacking District. Lined with overlooks, gardens, public art, food stalls, and greenery, this walk is one of the best things to do in the city, especially on a nice day. Go for a walk, sit with a book, and people-watch — the High Line is a must-see and a true favorite among locals.

Next to it, in the Meatpacking District, there’s the new building for the Whitney Museum of American Art (a museum that collaborates with the Met). Even if you don’t go inside, the building is worth seeing, as it is a work of art in itself. But I would recommend going inside as there is a wonderful exhibit of American art.

99 Gansevoort Street, Chelsea, +1 212 570 3600, whitney.org. Open Mondays, Wednesdays, and Thursdays from 10:30am-6pm, Fridays from 10:30am-10pm, Saturdays and Sundays from 11am-6pm. Admission is $25 USD and pay-what-you-can on Fridays from 7pm-10pm (advance tickets strongly recommended).
 
Enjoy the view from the Empire State Building
After you finish up with lower Manhattan, jet up to this historic landmark. Standing 1,453-feet (443 meters) tall and completed in 1931, the 1930s art deco interior of this building is absolutely beautiful and the view from the top is breathtaking. It’s one of the most iconic buildings in the city and you can get a real feel for how densely populated New York is as you take in the view. Get here early or during lunchtime to avoid the lines and tour groups.

350 5th Avenue, Midtown, +1 212 736 3100, esbnyc.com. The observation deck hours vary greatly by season (with week-to-week differences). Check the website for updated hours. Admission is $44 USD to the 86th-floor observatory and $79 to the 102nd & 86th-floor observation decks. Get your skip-the-line tickets here.

Marvel at Grand Central Terminal

Grand Central Terminal is the city’s historic train station. It was going to be torn down in 1975 but was saved by Jacqueline Kennedy, who raised money for its preservation. I love coming to the main concourse and looking up at the “stars” in the ceiling as everyone races to and fro. There’s also an amazing eatery in the basement called the Grand Central Oyster Bar & Restaurant. And for fancy (and expensive) cocktails, visit The Campbell and step back into the 1920s (dress code enforced). It was once the office of John W. Campbell, a member of the New York Central Railroad’s board of directors and finance tycoon from the 1920s.

89 E. 42nd Street, Midtown, grandcentralterminal.com. Open daily from 5:30am–2am. Book the only official Grand Central Terminal Tour with Walks here ($30 USD).

See the Lower East Side Tenement Museum
This museum highlights how immigrants from around the world lived during the late 1800s and early 1900s as they tried to make it in America. It’s a good follow-up to what you see on Ellis Island. You can only visit this museum via guided tours, and they need to be booked in advance. I like that live actors are used to portray and share the stories of newly arrived immigrants as it makes the experience much more memorable.

103 Orchard Street, Lower East Side, +1 877 975 3786, tenement.org. Open daily from 10am-6pm. Admission is $30 USD.

Other Options for Your Itinerary!

There are a lot of things to see and do in NYC. You will literally never run out of things to do here. It’s impossible. Some other options to add in if you’re not into museums or walking around as much:

1. See a TV Show – NYC is home to tons of TV shows that film here regularly. TV shows like Saturday Night Live, The View, The Late Show with Stephen Colbert, The Daily Show, Last Week Tonight, Late Night with Seth Meyers, and The Tonight Show with Jimmy Fallon all offer free tickets to their tapings. Tickets need to be reserved long in advance so you’ll need to plan ahead.

2. Explore the Bronx Zoo – Opened in 1899, the zoo spans almost 300 acres and sees over 2 million visitors each year. Home to over 650 different species, it’s a great place to visit with kids. Gorillas, birds of prey, bison — there is a huge assortment of animals here and you’ll definitely learn a lot during your visit!

3. See a Yankees/Mets/Rangers/Knicks Game – Like sports? NYC has some world-class sports teams. I’m not a big sports fan (the Yankees play soccer, right?), but games are fun when you have friends to share the experience with. If you have a chance and the desire, don’t miss a sporting event, because New Yorkers are serious about their local teams!

4. Take a Food Tour – NYC is a foodie city and there are tons of amazing tours that can introduce you to the best food the city has to offer. Devour Food Tours is my go-to choice as their tours are amazing and their guides are super knowledgable.

A few tours worth checking out if you want to eat your way around the Big Apple are:

• Scott’s Pizza Tours
• Foods of NY
• Famous Fat Dave’s Five Borough Eating Tour
• Secret Food Tours
• Beyond the Plate

5. See Live Stand-Up at Comedy Cellar – Some of the biggest names in comedy either started here or have done gigs here, including greats like Jon Stewart, Robin Williams, Kevin Hart, and Chris Rock. They have different shows depending on the day of the week although the weekend shows fill up so reserve in advance online. Some shows have up to 5 or 6 different comedians.

Tickets range between $14-25 USD but they often have a two-item minimum per person (food or drinks). For NYC, it’s a very reasonable super fun night out.

***

New York City is a big place with a lot to do and this list barely scratches the surface. Five days is barely enough to squeeze these activities in, let alone find time to visit boroughs like Queens and Brooklyn.

But if you’re pressed for time, following these tips will give you five days full of fun and excitement in the city that never sleeps!