First Time Guide to New York City 5 Day Itinerary by a native New Yorker (2023)

I’m so proud to be a native New Yorker and I love to help first timers plan their first trip to New York City. I’ve made a five day itinerary for NYC with advice on what to see and eat mostly in Manhattan for all budgets.

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If you are looking for more in-depth travel advice about Belgium and the Netherlands, I created a guidebook on behalf of Moon Travel about Amsterdam, Brussels, and Bruges. You can find this book on Amazon! First Time Guide to New York City 5 Day Itinerary by a native New Yorker (1)First Time Guide to New York City 5 Day Itinerary by a native New Yorker (2)

This is a local guide, so although I cover the famous sites, I encourage you to see the smaller neighborhoods/places that make New York special. The Big Apple has so much to offer year-round, so most of these tips can be also used over the holidays. There’s a FREE downloadable map with all the best places to see in New York City in 5 days.

FYI: This is asuggesteditinerary for fivedays, so not everything may be your cup of tea. Feel free to pick from the days (and activities), but keep in mind that New York City is BIG, so you change up this itinerary, you might have a lengthy train or taxi ride between places.

How long to spend in NYC? 5 days in NYC is actually the perfect amount if it’s your first visit. You can spend 3 days in New York City, but it’s cutting it close–and you’ll need to come back again. If you have only one day in New York City, you can still see Manhattan!

Before you visit New York City: Download Google Maps & the FREE map at the bottom with all mentioned places as well as Yelp for food. Google has recently really improved their offers for food recommendations.

How to get to NYC from its airports

If you’re on the East Coast, you can take Megabus directly to Manhattan. Otherwise, you will fly into JFK, LaGuardia, or Newark. JFK is easily accessible via the Airtrain & A train and/or LIRR. You can also book your own shuttle in between Downtown Manhattan and JFK/any other airport if you don’t want to worry about it. Uber is now also an option.

LaGuardia requires a bus and a train, but it’s a quick hop to Manhattan. Newark International Airport is in New Jersey, so plan on 30+ minutes on NJ transit. This is separate from New York’s subway system. You can click here for tips on how to use the NYC subway.

Where to Stay in New York City & How Much Spending Money You’ll Need

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New York is expensive. If you’re not on a tight budget, you’re best off staying off in Midtown or the Village if you can afford it since both locations make sightseeing easiest.Click for my insider guide to affordable hotels in New York City.

However, for those seeking a more alternative experience and/or lower price tag with a short train ride to the sites, stay in Astoria or Long Island City in Queens. In Brooklyn, look in Williamsburg, Dumbo, or Clinton Hill.

You might also find some affordable picks alongthe Lower East Side. You might also want to look into thePod hotel chain for affordable rooms in central locations. Click for my picks for affordable hotels in New York City

​For budgeting tips, read my master NYC on a budget post where all of the activities are FREE. Plan on spending at minimum $50+ per person on food, $20 per person on activities minimum, $100+ on the hotel (for one room), and extra if you plan on going out (cocktails are usually $10-15). Be sure to master happy hour as it will save you a lot of money. Please be sure to account for tips at restaurants as tipping is standard in New York City.

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I did not include this on the list: I highly recommend stopping to see a Broadway show, if that’s your thing. Book your tickets early and try first through the theatre itself to get the best prices in advance. In place of going out, see a show. Budget about $70-$300+ per ticket depending on the show and your sets. A friend of mine was able to get tickets to a major Broadway show for just $70 per seat. Off-Broadway is a great option for those on a tighter budget.

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What to see in NYC in 5 days!

Day 1: The Must-Sees with a Twist

This day is all about experiencing New York City at it’s best: pizza, history, and iconic views.

Visit the 9/11 Memorial ($2 Reservation Fee; otherwise free to visit). Note: Please be respectful of those who passed away here and don’t remove the flowers or take smiling selfies. Walk a few streets over to see the WoolworthBuilding, one of New York’s prettiest early skyscrapers dating back to the 1910s.

Walk up towards Chinatown. Be sure to bring cash and trust me when I tell you that the bags offered to you on the street arenotreal Chanel bags. You can click for this insider’s guide to Chinatown written by a friend who is from Chinatown. Annie includes a bit of history as well as her favorite restaurants in Chinatown. I personally love to always stop off for bubble tea!

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After you eat, consider visiting the Tenement Museum to learn about New York’s immigrant past–and what living in Chinatown was like barely 100 years ago. You need to reserve ahead for tickets. Click to read more about the Lower East Side.

Walk across the Brooklyn Bridge. No matter how many times I walk across the Brooklyn Bridge, I never ceased to be amazed by its impressive building.

Stop in for a coffee at Brooklyn Roasting Company for some Brooklyn vibes and a good cup of coffee before walking to theBrooklyn Promenade for a panoramic view of Manhattan. Click for a complete guide to downtown Brooklyn!

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Have Juliana’s Pizza for dinner. Grimaldi’s is not as good as it once was. This famous pizzeria has delicious, affordable thin crust pizza cooked to perfection. Its location under the Bridge makes it even better around sunset.

Get drinks in trendy Williamsburg at Union Pool or Night of Joy to enjoy the view of Manhattan from the roof, especially in summer. Not into the hipster scene?Head back to Manhattan via the Brooklyn Bridge to enjoy the view of the lit-upskyline before walking down to Battery Park to catch the free Staten Island ferry for amazing views of the Statue of Liberty. You can click for my favorite free viewpoints in New York City here!

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Day 2: The Intellectual / The Partier

This day involves walking through some historic neighborhoods before taking in some culture via films and books. For those into partying, you’ll still want to walk the High Line, experience Greenwich Village as well as explore Chelsea, which has some of New York’s best nightlife.

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Walk theHighlinefor an amazing view of Manhattan’s skyline from above in a modern green space that used to be train tracks. The Highline is a public park that spans quite a few blocks, so give yourself at least an hour if you come here to enjoy the views!

Stop in Chelseafor a delicious brunch in any of the stalls before walking around chic Chelsea. This area, which used to be the meatpacking district, has great boutique shopping and antique shopping.Click for your Chelsea brunch guide!

Walk down Greenwich Avenue or West 4th Avenue for scenic houses and interesting shops in Greenwich Village. Pass the Stonewall, the birthplace of the gay rights movement. There are many great cafes and coffee shops in this area.

Walk towards the iconicWashington Square Park (next to New York University). People watch & play a chess game before walking up to Union Square, which has a great weekend farmer’s market in addition to normal shopping. Stop inthe Strand,one of New York’s best independent bookstores. For dinner, you have so many great options from Japanese to vegan to pizza. Enjoy!

Note: It shouldn’t take long to walk (maybe 1 hour from Chelsea market down to the Union Square), so you should have plenty of time left for museum-going or must-sees (e.g. Top of the Rock) if you set out early. Personally, I’d skip the Top of the Rock if you go to a rooftop bar.

At night, head back to the Village to visit one of New York’s many (pricey) speakeasy bars, including Employees Only or Please Don’t Tell. Reserve ahead and dress well as you might not get in otherwise. Chelsea/the Meatpacking District is one of the main areas for going out in New York (if that’s your thing). The Standard is famous for its rooftop bar although it’s difficult to get into.

If chic cocktail bars aren’t your thing, New York has a lot to offer in terms of alternative culture. Check out the IFC movie theatre for rareindie movies or Comedy Cellar for late-night laughs (beware of the drink minimum).

Need a late-night snack? Veselka has delicious 24-hour Ukrainian borscht and perogies. (Yes, that restaurant out of Nick and Nora’s Infinite Playlist.)

Day 3: Iconic New York

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Start your day off in the beautiful Grand Central Terminal. This historic train station is one of the most famous filming locations in New York City. I love people watching here although try to stay out of the way. For something off the beaten path, find the whispering gallery where your voice echoes!

Head to the New York Public Library and pass the landmarks (the Chrysler & Empire State Building) to take in the architecture. My favorite is the Chrysler building, which was known as the ugliest building in New York when it was built.


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For lunch, eat at Shake Shack with the rest of Manhattan in Bryant Park. (Dress warmly in wintersince there’s no seating!). In Bryant Park, you can watch people ice skate in winter while you eat! Nearby, I have a soft spot for browsing the giant Macy’s in Herald Square.

If you’re an art lover, visit the Museum of Modern Art. MoMa is a world-class museum for a reason and I strongly recommend checking the recent exhibitions to see what is on.

If not, enjoy shopping along Fifth Avenue. The Christmas windows here during November and December are spectacular andfree. My personal favorite is Bloomingdale’s!Read more tips about New York over the holidays.

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Dinner doesn’t need to be expensive to be good. Go toHalal Guys for cheap/delicious take-out chicken and rice, Pio Pio for fantastic Peruvian food, or Empanada Mama for empanadas. After dinner, watch the sunset and take in the incredible skyline (with a cocktail in hand) at the Pod 39 Rooftop.

Enjoy the bright lights of Times Square at night. (Trust me, it’s like daytime.) If you’re on a budget, I like to head to Hell’s Kitchen formore budget drinks and late-night snacks.

Day 4: The Perfect Classic NYC Itinerary

Pick up a bagel with lox from Zabar’s or get a boozy brunch at Calle Ocho. To be honest, anywhere with a good bagel and a coffee should work as long as it’s not Dunkin Donuts.

Head to the American Museum of Natural History if you’re with kids OR the Metfor a few hours! In the Met,I love the Egyptian temple, Musical Instruments, Armor, and pre-20th century art. Don’t miss the rooftop garden for amazing views. Bring your own yogurt for a Gossip Girl photo. (XOXO)

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In good weather, you could spend the whole day in Central park lounging, but the Met is one of my favorite museums in the world with a world-class collection.The Met doesn’t have suggested admission anymore, but it’s still a great museum. The American Museum of National History is also a fantastic museum and better suited to families as well as science lovers. Click for a guide to the Upper East Side!

Head to Central Park.I recommend finding the Belvedere Castle, the Bethesda Terrace, Sheep Meadow for lazy picnics, and the Boathouse. If you’re a runner, I strongly recommend trying to run the Reservoir one morning.

In summer, check the Summerstage program ahead for free music shows! This yearly music festival in New York brings in well-known as well as upcoming artists for free shows in Central Park. It’s great to make a day out of it.

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For a nicer modern meal, visit the Thalia or the Russian Tea Room. For a casual, very New York meal, try a (famous) NYC hot dog? Don’t buy it from a cart; Only buy from Gray’s Papaya with a smoothie like a local. Have the realNew York famous cheesecake at Junior’s for dessert.

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Day 5: The Culture Lover (Queens)

Queens is where I grew up. (Yes, not everyone lives in Manhattan.) It was named Lonely Planet’s #1 destination in the world in 2015 due to its amazing food and culture. Really.

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Take the train to Astoria to visit the Museum of Moving Image in the morning. For anyone who is a movie buff or has kids, this museum will be heavenly. They have old prop sets from classics, such as Seinfeld, interactive exhibitions, and a lot of movie props (even from Star Wars).

Astoria itself is a neighborhood in Queens that has historically been Greek and you can still find great Greek food here. That said, it’s rapidly changing as more millennials move in. Click for a guide to Astoria.

Lunch: visit nearby Jackson Heights for the bestLatin American food in NYC or Indian food. (Yelp!) Jackson Heights is a diverse neighborhood with incredible food fromso many countries. (I highly recommend checking out the Queens Night Market if you’re lucky enough to be in town later that evening!)

The rest of the Day gives you lots of options. Stop off at Flushing Meadow Park (especially in summer!) to see the iconic Unisphere and check out the NYC Panorama, which is a miniature version of New York City in the modern Queens Museum of Art.

Into art/sculptures? Visit the Noguchi museum for beautiful Japanese sculptures and a zen garden, PS1 for avantgarde exhibits, or the free Socrates Sculpture Park for free sculptures.

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Into beer? Head to the Bohemian Beer Garden to relax or one of the many microbreweries popping up all around NYC (Singlecut Beersmiths / Rockaway Brewing company).

For shopping, catch the LIC flea market on the weekend. Don’t miss the gorgeous retro-chicSweetleaf coffee shop if you’re in the area, which turns into a bar a night.

For dinner, head to Flushing (Stop on 7 Subway: Main St). Decide what kind of Asian food you’re seeking and check on yelp. (It’s going to be a hard decision.) After dinner, stop for bubble tea or Chinese pastries. You can even do private room karaoke if you look for KTV signs. You can click to read more about Flushing, including my favorite picks for dinner.

Last thoughts: Plan Ahead.

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New York is so large. I sometimes joke that you need about two weeks to just cover the major sights, which is true since I didn’t even include Coney Island (Brooklyn). I didn’t even cover every borough here!

However, five full days in New York City is a perfect start to feel at home in New York. At a minimum, you should have the hang of the subway by the time that you’re done. Below, you’ll find a free offline map with all the places mentioned here that you can download for offline use!

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Have you been to NYC? How many days felt right? What was your favorite place?

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