A 5 Days in New York Itinerary, Written with Love by an Ex-New Yorker

It’s a major oversight that I haven’t written about New York City at all in the nearly two years I’ve had this travel blog. After all, New York was my home for 9 years, and as a result I know the city better than any other in the world.

I guess New York is such an overwhelming topic, and to try to consolidate my 9 years of wisdom into a quick New York City itinerary in nearly impossible. I wanted to create an itinerary that represents a wide span of the city – not just the iconic museums and buildings, but the independent bookstores, cozy cafés, and authentic ethnic restaurants that really make New York what it is.

This 5 day New York itinerary is made with first-time visitors in mind, but I think even New York veterans can find something new and exciting on this — especially on days 4 and 5, where I zero in on Queens and Brooklyn.

5 days in New York City is kind of the bare minimum to get a good idea of Manhattan and still get to see a few of the other boroughs. Of course, there’s so much more you could do – 9 years in the city and I’m still discovering new sides to New York.

Note: NYC is one of the safest big cities in the U.S., but I still highly recommend having travel insurance – especially if you are from outside the U.S. Due to a lack of a national health care system, obtaining health care in the U.S. is incredibly expensive if you have an accident or medical emergency while traveling abroad. I use and personally recommend World Nomads as my travel insurance to cover me all around the world.

5 Days in New York: Day One

Downtown Manhattan, the Staten Island Ferry & Downtown Brooklyn

Walk from Union Square down Broadway

Note: This post contains affiliate links, which means I may receive a small commission if you purchase something through one of these links. Thank you for supporting the free content on this site! For more information on affiliate links and cookies, see my disclosure page for more details.

Your first day in New York should be about getting a feel for what makes this massive city so quintessentially New York. Union Square is as good a place as any to start – stepping off the subway here, for me, will always feel like peak New York. Whirl your head around and up and marvel at the buildings around you: you’re in freaking New York City!

Walk down Broadway, where you’ll pass a few sites worth noticing. The Strand on the corner of 12th and Broadway is my favorite bookstore in the world, boasting 18 miles of books. Stop in and browse the impressively curated selection of new and classic books on the ground floor, or go on a treasure hunt through the used dollar book carts out in front. There are also tons of rare first editions and leather-bound books for my fellow mega-book nerds.

Just a few more blocks down on 10th, Grace Church is worth a quick stop into. I’ll always have a soft spot for this church since my first home in New York was right across the street (making hungover Sundays a painful situation – but I digress).

Explore arty SoHo by foot

Keep walking and you’ll reach Houston Street, where SoHo begins. Walk around some of the cute side streets – I especially like Crosby, Mulberry, Mott, which are parallel to Broadway but to the East.

There are countless cute boutiques to stop in if you want, but I just love the experience of walking down these streets. If you’re about due for a coffee, La Colombe on Lafayette between Prince & Houston makes some of the best espresso drinks on this planet. Book nerds like me will adore the Housing Works Bookstore & Café on Crosby between Prince & Houston as well.

Street art lovers, take note: the SoHo/Nolita area is probably the best place for street art in Manhattan. There’s too much to list here, so here’s a super-comprehensive guide to the area’s best street art.

If you’re into quirky contemporary art, now is a good time to pop over to the New Museum on Bowery between Stanton & Rivington. Otherwise, I recommend the Tenement Museum for a thoughtful look into what life was like for low-income New Yorkers and immigrants in the early 20th century.

Feast in one of the U.S.’s best Chinatowns

Once you’ve had sufficient time to wander Soho, you’ve probably worked up an appetite. You can safely skip Little Italy as it’s rather gimmicky and has been pretty much overrun by Chinatown. If you really want pizza, may I direct you instead to the oldest pizzeria in the United States, Lombardi’s on Spring Street.

If you keep walking south, you’ll hit Canal Street which is pretty much the heart of Manhattan’s Chinatown. Try not to get lured into purchasing fake bags or sunglasses, and just gawk at the bustling atmosphere instead.

Chinatown is fantastic and I could write an entire blog post all about it… but I’ll just give you a few quick recommendations here. For delicious hand-pulled noodles, try Spicy Village. Their big tray chicken is unmissable and will feed 2-3 hungry people for under $15 (and it’s BYOB as well, so just pick up some beers from the bodega next door if you want to feel peak New York). Note: Are you gluten-free? Check out this gluten-free guide to New York.

For dumplings, Joe’s Shanghai has the best soup dumplings I’ve been able to find in New York. If you’re into dim sum, Golden Unicorn is my absolute favorite but Nom Wah Tea Parlor and Jing Fong are also close contenders.

Finally, I’m obsessed with Xi’an Famous Foods’ cumin lamb noodles, but there are locations all over the city so it may be best to save it for a different day of exploring. For dessert, I love the egg custard tarts at Tai Pan Bakery on Canal Street.

Marvel at the architecture of the Financial District

After you’ve filled up and rested your feet a bit, continue downtown. One of my favorite buildings is a residential building by Frank Gehry, the architect behind Prague’s famous Dancing House. It’s located on 8 Spruce Street right by City Hall.

Continue on Wall Street and the Financial District. Here, you’ll find the Fearless Girl statue facing the iconic Wall Street Charging Bull statue.

Say hello to Lady Liberty

Keep walking a bit further south. You’ll be by the Staten Island Ferry which is free for all to take, with amazing views of New York’s harbor and its most famous resident — The Statue of Liberty.

If you prefer an up-close visit with Lady Liberty, you can schedule an actual tour of the Statue of Liberty or a combo Statue of Liberty-Ellis Island tour.

I haven’t done either as I’ve never actually gone to see the Statue of Liberty up close. It’s funny how when you live in New York, you often don’t get around to doing all the NYC itinerary musts. But I know many people want to see the Statue of Liberty as part of their New York trips, so if that’s something you want to do, I recommend booking your tour tickets in advance as they often sell out in high season (June-August and Christmas).

»» Book a Statue of Liberty tour here «« 

There’s also an affordable 60-minute cruise passing by the Statue of Liberty and Ellis Island, but it doesn’t let you visit either on foot.

There’s also a free option! Enter… the Staten Island Ferry, aka the best cheap-o hack for budget travelers and in-the-know New Yorkers who don’t want to spend like $40 every time someone comes to town.

If you want to hack a free trip to see the statue, which is what I always did when showing people around NYC, just hop on the Staten Island Ferry, ride it over, hop off and hop right back on (as there’s not much to see in Staten Island). Roundtrip, it will take you about one hour and will be a nice break from being on your feet so much!

An alternate idea (and truly on the other side of the price spectrum) is to take a helicopter tour over Manhattan!

It is a true bucket list item, and it is a great way to see the city (and Lady Liberty!) in a new light. Click to check prices and availability, keeping in mind that you should book in advance if this is definitely an activity you want to include on your NYC itinerary.

Pay your respects at Ground Zero

After you’ve seen the Statue of Liberty, head a bit north to see the 9/11 Memorial, a must for anyone’s New York itinerary. It will make you feel quite somber to be in the presence of such tragedy, but it’s absolutely worth the visit and helps you understand what New Yorkers have been through and why they are so resilient.

Local Tip: The lines can be quite long here, especially if you visit in the peak season (which is really any time that’s not January, February, or March). I highly recommend booking a skip-the-line ticket online in advance if you plan on visiting and you have a busy New York City itinerary scheduled. This will let you skip waiting in line, doesn’t need to be printed out, and includes a timed-entry admission to the museum and memorial and an audioguide.

Soar to heights of the Western Hemisphere’s highest building

One thing that I think is so beautiful about New York’s spirit is that it’s unbreakable. When terrorists knocked down New York’s most important building and ended the lives of nearly 3,000 (and leaving many thousands of first responders with chronic health conditions), the city could have decided the pain was too great to rebuild.

Instead, New York decided to build an even taller building in its place, to create a new symbol of strength and beauty. It took nearly the entire time I spent living in New York for the building to be built, but when it was finally done, it was beautiful.

Now the tallest building in the Western Hemisphere and the sixth largest in the world, visiting this beautiful observatory is a testament to New York’s ongoing strength, bravery, and grit.

Predictably, the lines to get in are insane, so I highly recommend booking a skip-the-line ticket which lets you skip the ticket queue (you’ll still have to wait for security and the elevator).

»» Book your One World Observatory tickets today and save time «« 

Stroll the beautiful Brooklyn Bridge

After you’ve seen the memorial, take a walk across the iconic Brooklyn Bridge please, watch out for cyclists as many people do use this bridge to commute daily (or actively go out of their way to avoid it because the tourist traffic is so insufferable).

Once you’ve crossed, take a seat somewhere in Brooklyn Bridge Park and watch the sun go down for an epic sunset and stunning views of Downtown Manhattan.

Find an epic dinner in Brooklyn

For dinner, the world is your oyster – this is New York, after all, one of the best places to eat in the world. If you didn’t have pizza earlier, I recommend Juliana’s – the pizza is even better than next-door Grimaldi’s (in fact, it was voted the best pizzeria in the entire U.S. in 2015 on TripAdvisor) but it’s not often in the guidebooks so there’s usually no line. If you do this, be sure to save room for dessert at the delicious Brooklyn Ice Cream Factory just down the street.

If you’d rather have something different, here are a few of my favorite Brooklyn restaurants. None of these are within walking distance of the end of the Brooklyn Bridge so at this point you’ll want to call a cab/Uber or hit the subway.

For something different, try Ethiopian at Ghenet in Park Slope. For a modern take on ramen, try Chuko in Prospect Heights. For upscale farm to table fare with an Italian twist, try Frannie’s on Flatbush Avenue (sadly, reader Bettina just informed me that Frannie’s is now closed – read this lovely eulogy to my beloved pizza place!)

I used to recommend Pok Pok for Thai, but that too has apparently closed (such are the perils about writing about a dining scene as mutable as New York’s!) I haven’t personally eaten here, but the new Thai restaurant Ugly Baby gets rave reviews despite the silly name. For tapas, I’m obsessed with La Vara. For those on a budget, you can’t go wrong with Shake Shack – New York’s closest attempt at imitating the perfection that is In-N-Out Burger (what, I’m a California girl at heart!).

Pretty much all of these places are within a stone’s throw of tons of fun yet relaxed bars, if you have any energy left after that ridiculous amount of walking I had you do. If not, head home and rest up for the next day.

5 Days in New York: Day 2

West Village, Chelsea, and Midtown

Stroll around Greenwich Village

Start your day at Washington Square, which is the heartbeat of New York University and home to the famous Washington Square Arch. It’s fun to people-watch here by the giant fountain in the middle if it’s a sunny day.

If you’re a dog creeper like me, head to the dog parks in the southwest corner to gawk at all the adorable New York canines. There’s also often plenty of street performers if that’s your thing. Remember to tip your performers if you enjoy their work!

Wander west to the West Village

Keep walking west on 4th Street/Washington Square South and explore the West Village. It’s easy to get lost here, as the streets snarl and confuse in the most delightful, Alice-in-Wonderlandian of ways… For example, West 4th intersects with West 10th, and Waverly Place intersects with itself. Logical.

Walk until you’ve worked up an appetite, then find a place for brunch – that most New York of meals.. A few favorites are Westville for some unpretentious veggie-friendly fare, Tartine for decadent French food (which you’ll likely have to wait in line for – the quintessential New York experience), or Jack’s Wife Freda for delicious Middle Eastern food. Those on a budget can grab a delicious falafel at Taïm – I love their sweet potato falafel.

But perhaps the coolest place to have lunch is at The Little Owl – which is the delicious restaurant beneath the apartment from Friends! If you’re a fan of the classic sitcom, you’ve got to make a quick lunch stop here, if not to pay homage to the show then at least to eat some delicious food (I love the gravy meatball sliders, yum!)

Alternate idea: explore the Village through your stomach! This Greenwich Village food tour covers the history of the Village from the perspective of a local, taking 3 hours and including 6 tastings, including New York classics like the hot dog, a true New York deli sandwich, pizza, and other secret treats that will be revealed on the day of the tour.

»» Book your Village food + walking tour here! «« 

There aren’t too many landmarks in the West Village: mostly you’ll be gawking at the beautiful brownstones and philosophizing about the moral lows you’d sink to in order to be able to afford an apartment here (let’s just say that Friends wasn’t exactly realistic…).

There are a few notable historic pubs in the West Village, and that’s about it for sights. Stonewall Inn on Christopher Street has been the heart of the gay rights movement, since the riots that took place there in 1969. As you walk north towards Chelsea, stop at or pass by the White Horse Tavern, the former watering hole for musical and literary legends like Bob Dylan, Hunter S. Thompson, and Jack Kerouac. I recommend ordering a whiskey neat, no matter the time of day, and feeling like a BAMF.

Hit up the incredible (and incredibly busy) Chelsea Market

Keep walking north and you’ll hit the Chelsea Market on 9th Avenue and 15th street. Give a big fat middle finger to the Anthropologie store there, where I slowly lost my sanity working for 18 months (kidding/not kidding). Continue inside to some of the gourmet shops within the Chelsea Market.

A few favorites are Fat Witch for insanely good brownies, the Chelsea Wine Vault for super-knowledgeable wine sellers (and sometimes free tastings!), the Doughnuttery for adorable mini-donuts, Heatonist for artisan hot sauces, Los Tacos No. 1 for surprisingly authentic and delicious tacos (certified by a Californian),  and Num Pang sandwich shop for delicious banh mi.

If you just need coffee, 9th Street Espresso has some amazing iced coffee and great espresso drinks. You can also go on a Chelsea Market food tour!

Stroll the highline, New York’s elevated park

5 days in New York itinerary

I recommend getting at least some sort of thing to snack on to-go, as you’ll be walking The Highline next. Depending on the time of year and time of day, this can alternate between lovely and so ridiculously crowded that it’s not anywhere close to enjoyable.

If you need to retreat from the crowds, Terroir Wine Bar is one of the best places to day drink and hide from people. If the crowds aren’t so bad, enjoy the view of fancy buildings and some street art, and walk up to about 20th or 23rd Street.

Snag a great view of NYC with a quick midday cocktail

Exiting the Highline on 23rd street, walk east until you reach the Flatiron Building on 5th Avenue. This is a great spot for photos and it’s one of my favorite buildings in New York.

If you want a view from above, check out 230 FIFTH which has a cool rooftop bar. Drinks are overpriced, but it’s worth it for an epic view over the city, with an especially great view of the Empire State Building — New York’s most iconic.

Be surrounded by books

Keep heading north towards 42 Street. You can stop at the Morgan Library & Museum on Madison Avenue along the way but it’s rather expensive at about $20. But for book nerds, admission to Pierpont Morgan’s 1906 Library alone is worth the cost of admission. Up to you.

From there, walk towards the New York Public Library with its famous twin lion statues. The architecture of the building is stunning: marble floors, ceiling murals, chandeliers — this ain’t your average public library, that’s for sure. The Rose Room is the most famous part of the library, so be sure not to miss it!

Marvel at the ceiling of Grand Central

Finally, stop off at Grand Central Station, a New York landmark for its beautiful vaulted ceilings. This place is amazing for photographs and just for watching the chaotic symphony of New Yorkers going about their nightly commutes.

If you feel really classy, stop for dinner at the Grand Central Oyster Bar. If you’re poor like the rest of us, check out this guide to some of New York’s best cheap eats (psst- this is a great time to visit a branch of Xi’An Famous Foods — there’s one on 45th Street!)

Cap off your night with a 2 hour night lights harbor cruise (better for kids) or a romantic champagne sailing cruise (better for couples) to see some gorgeous skyline views of New York. Keep in mind food and beverages are not included so plan accordingly.

5 days in New York: Day 3

Uptown, Museums, Central Park, & More

Start the day with a great view of the city

This post is assuming you’ll pick one of the main observation decks in midtown NYC, either Top of the Rock of the Empire State. I prefer the Top of the Rock because you can see the Empire State Building, my favorite building in the entire city.

However, many people prefer to go up the Empire State Building itself (or go to both). Besides the view, the lobby is incredible: murals of 24K gold and aluminum leaf form a beautiful art deco tapestry, and the Dare to Dream exhibition detailing the construction of the building is quite fascinating.

If you visit the Empire State, I strongly recommend getting a skip-the-line ticket like this one. The general ticket will result in a lot of queueing and isn’t really worth it, especially given how little time you have in New York. For extra speediness, opt for the Express ticket which lets you skip all the lines and has a flex date feature so you can visit any day within one month of your chosen date, so in case the weather doesn’t cooperate, you can easily visit a different day.

»» Book your express skip-the-line ticket here to save time «« 

However, many people pick the Top of the Rock because you can get great views of the Empire State Building. And in my opinion, the Empire State is the best part, so if you’re going to spring for one or the other on your New York itinerary, make it the Top of the Rock.

I never did it when I lived in New York, and went for the first time earlier this year. It’s amazing and well worth the price, I think (just make sure you go on a good weather day!). Take in a view of the Empire State Building and the Chrysler Building and be sure to snap plenty of photos for Instagram so you really get your money’s worth.

Note: Again, if you hate lines as much as I do, I strongly recommend that you buy your tickets in advance online. If you just show up to buy your ticket in person, you likely won’t be able to get in right away and will have to come back at a later time – or even a later day – therefore waiting in line not once, but twice. If this is something you want to do, do not save it until the last day as there is a decent chance you won’t be able to get in.

PS – the guys running the line at Top of the Rock make the TSA (American airport security) seem like warm, friendly puppies. Don’t take it personally. 

Visit some of Midtown’s landmarks

Afterwards, stop by the iconic St. Patrick’s Cathedral just across the street. This is probably the most impressive religious structure in all of New York, and a definite must-visit regardless of your religion (or irreligion, as the case may be). Entry is, blissfully, free.

Next, visit the MOMA (Museum of Modern Art). This museum is absolutely massive but you’d be a fool to miss it, as it has probably the best collection of modern art in the entire world. If Vincent van Gogh’s Starry Night isn’t being loaned out elsewhere, this is the place to see it!

They also have fantastic temporary exhibits in addition to great impressionist art. Note that if you’re on a budget, you can visit for free on Friday nights, so keep that in mind and maybe prioritize a visit then. Skip-the-line tickets are also available if you’re not planning to visit on a free Friday, which I definitely recommend investing in as the lines here can get cray.

»» Pre-book your tickets to the MoMA here «« 

Pop over to Columbus Circle, the gateway to Central Park

Next up, walk towards Columbus Circle. You can pop into the iconic Tiffany’s on Fifth Ave if you’re an Audrey Hepburn fan (don’t forget your danish and to-go coffee – you can skip the evening gloves though). The famous Plaza Hotel is another well-known film spot, home to works of art such as Home Alone 2 😉 Still, the lobby is absolutely stunning, and definitely worth popping into.

Foodie note: this part of New York is where culinary dreams go to die, unless you’re insanely rich and can afford to eat at places like Jean Georges where you’ll easily spend upwards of $100 per person. There’s very little in the way of good restaurants to eat around here. Most will be just above decent, but priced atrociously expensively. The Infatuation is my favorite guide to New York restaurants, and here are their recommendations for the culinary hellhole that is the area around Columbus Circle. I’ve never eaten at any of these so I can’t vouch for anything personally.

Instead, I recommend just grabbing something simple — now might be a good time for some street meat, aka halal. You can’t go wrong with chicken over rice (if you’re extra hungry and screaming for carbs I recommend asking for a pita on top too.) Careful with the hot sauce – it’s super hot, and the guys will go crazy with it if you say you like it spicy. I don’t have any particular place to recommend, just look for somewhere relatively busy and well-trafficked.

Get lost in Central Park

Now that you’re fed, you’re at the gateway to Central Park. Central Park is almost like a city unto itself. What you do in Central Park depends on what you’re interested in. If it’s just people-watching and strolling, walk away — you’ve got literal miles of walkways to choose from. For a more scenic side, check out the Lake near the Central Park Boathouse Restaurant. If you’re a Beatles fan, check out Strawberry Fields, dedicated to John Lennon (this is where you’ll find the famous “Imagine” memorial where people often leave flowers). The best people-watching and chilling spot is Sheep Meadow – watch out for topless hippies (it is legal for ladies to be topless in NYC, FYI – #freethenipple!).

There’s also Belvedere Castle, the Friedsam Memorial Carouselthe Conservatory Garden, and the famous Alice in Wonderland statue — so go on a treasure hunt for these if you feel like it! If you really want to cover Central Park in depth, some companies offer affordable guided walking tours.

Visit New York’s (or even the world’s) best art museum

another fun thing to do in New York for first timers!

After relaxing in the park for a bit, it’s time to get your culture on. The Met (short for the Metropolitan Museum of Art) is an absolute must-see, if not for the art, at least for the amazing architecture and iconic steps.

Admission used to be pay what you wish — as of 2018, it’s now a steep $25 for out of towners. It’s unfortunate, but I think it’s well worth the cost of admission, as there’s really something for everyone here. Since you have to pay the mandatory fee now, you might as well book online and skip the line for no added charge.

There are countless things to see here, so just pick a few rooms and focus on those. There’s simply no way to see it all. My favorites are the Impressionists, the Egyptian section, the Native American art, and the insanely luxurious European applied arts on the first floor.

If you’re not an art fan or if you have young kids in tow, the American Museum of Natural History is also fantastic (book tickets in advance here to avoid lines).

I’ve come here at least 10 times (hello, teacher days!) and it’s incredible each and every time. The dinosaur skeleton replicas cannot be missed! Also, don’t forget to take in a show at the Hayden Planetarium, where Neil de Grasse Tyson’s butter-like voice will soothe you as he takes you through a ridiculously psychedelic cosmic journey.

Dine somewhere nearby

By around now, it’ll probably be close to dinner time. Despite my many years living in the city, I still don’t know this part of town well for restaurants, so I’ll direct you to the Infatuation yet again for recommendations on where to eat near The Met or Eater for where to eat near the Natural History Museum.

Both the Upper East & West Side are rather on the expensive side, so if you’re trying to save some cash, head down to Hell’s Kitchen east of Times Square for some delicious Thai food. I love Wondee Siam for traditional Thai and Larb Ubol for the spicier Thai food from the Isan region.

Visit Times Square all lit up at night

A must for New york newbies - Times square!

And of course, end the night taking in the bright lights of Times Square! Yeah, Times Square is a bit of a shitshow, but it’s a quintessential New York itinerary stop for a reason.

By day, it’s easy to get angsty at the aggressive Elmos and ladies in body paint hounding you for photos, but at night even I find Times Square dumbfounding, and – at risk of having my New Yorker license revoked – a bit magical.

5 days in New York: Day 4

Off the Beaten Path: Food & Culture in Queens

Quick note: Queens is probably my favorite borough in New York. It lacks the freneticness of Manhattan and the relentless hipper-than-thou feel of North Brooklyn. It’s underrated as hell, and you should definitely save one of your 5 days in New York City for it. I’m going to lead you through all my favorite parts of it on a one-day epic Queens tour.

Start your day at the Roosevelt Island tram

What to do in New York in 5 days - ride the Roosevelt Island cable car

Start your day with a scenic gondola ride in New York — all for the price of a MetroCard swipe (that’ll be $2.75, unless the MTA has further price-gouged since I was in NYC last June, which is quite probable). You’ll be taking the Roosevelt Island Tram, which has an entrance in the Upper East Side of Manhattan on 60th street and 2nd Avenue (closest subway stop: Lexington Ave-59th St., NQR or 456 trains), with excellent views of both Uptown and Long Island City.

The views are what you’re really going for, here, as Roosevelt Island isn’t that exciting – it’s just a residential area. If you want, you can take something called the Red Bus, which will take you around the island for 25 cents. Or you can just hop on the F train and make your way over to Queens.

Stroll around Long Island City

Start in Long Island City, the neighborhood right across from Manhattan.

You can check out some interesting contemporary art at P.S.1 (a branch of MoMA – your ticket to the MoMA should get you free admission here). There used to be some amazing graffiti right nearby here at 5 Pointz, but they got destroyed in order to make room for condos – sadly, not that unusual in NYC these days.

Afterwards, take the quick walk over to Gantry Plaza State Park for some of the best views of Upper Manhattan and the 59th Street Bridge.

Hop back on the subway (or walk if you’re feeling ambitious) to the next museum worth seeing in Queens – the Museum of the Moving Image, which explores the history of cinema through interactive exhibits as well as frequent showings.

You’re probably getting hungry – but don’t get tempted to eat just yet! Next stop is Jackson Heights, one of the most diverse ZIP codes in the entire United States.

Eat your way through NYC’s most diverse & delicious neighborhood

Get off the subway there and walk in a variety of different directions depending on what your heart desires for food. Himalayan food reigns supreme here. My favorite is Lhasa Fast Food which is quite literally hidden in the back of a phone shop. But Patola Cart‘s street stall is a close second for delicious momos (Tibetan dumplings).

There’s also plenty of other options: Rajbhog or Dosa Delight for Indian dosas and chaat, the various Mexican street carts lining Roosevelt Avenue between 75th and 85th street which make insanely good sandwiches (tortas/cemitas), the list goes on and on… Thai food is especially well-represented with a walk 10 minutes away to to nearby Elmhurst where Khao Kang is a standout amongst other perfectly good Thai choices.

Head to Flushing Meadows

Next up is the Queens Museum at Flushing Meadows-Corona Park. I know, I know, another museum — but stay with me here because this one is special! This hosts an entirely miniature version of New York City that contains almost 900,000 structures, literally every building in the city that existed before 1992. 

You can continue checking out Flushing Meadows-Corona Park, which is Queens’ answer to Central Park. The coolest thing to see are the leftover structures from two former World’s Fairs that were hosted here: in addition to the mini-NYC you saw at the Queens Museum, you can also find a 12-story globe (the Unisphere) and a UFO-shaped pavilion.

The New York Hall of Science is also here, and great for little kids if you happen to be schlepping them around with you – or if you’re a kid at heart. You could also check out the Queens Botanical Garden here if you are so inclined!

Explore NYC’s biggest and best Chinatown

Finally, you’ll stop in my favorite part of Queens: Flushing Main Street. Exiting the train at Main Street-Flushing is pretty much the closest thing to going to China. It’s pandemonium for the senses in all the best possible ways.

I have way too many recommendations on where to eat here, but here goes: Dumpling Galaxy for dumplings (or the original Tianjin Dumpling House located in the Golden Shopping Mall), White Bear for spicy wontons, Spicy & Tasty for decent Sichuan food, Nan Xiang Xiao Long Bao for Shanghai soup dumplings, orrrr go full Korean with some KBBQ at Mapo (recommended if you’re traveling with a group as KBBQ for one is a bit depressing, not that I speak from experience….).

If your feet are tired, you can get pampered with a $20 per hour foot massage at nearby Coco Spa, just around the corner from the Golden Shopping Mall. Just beware that they will hound you for tips and that $20 massage can easily become $30 if you’re a pushover like me.

Read Next: 37 Ways to Get Off the Beaten Path in NYC

5 Days in New York: Day 5

A perfect Saturday in Hipster Brooklyn

*NOTE: If one of your days in New York happens to be a Saturday, shuffle around this itinerary to make this day your Brooklyn day so you can check out Smorgasburg and the Brooklyn Flea.*

Have breakfast like a true New Yorker

There are so many cool things to do in Brooklyn, so get an early start today. If you haven’t had the classic bacon egg & cheese from an NYC bodega (deli) yet, this is when I advise you to do so! Literally any bodega will do, even though there are better ones than others… but if you’ve only got 5 days in New York you’ve got to prioritize.

Head to Brooklyn Botanic Garden

Then, start the morning at the Brooklyn Botanic Garden. Depending on the time of year, you may see tulips, cherry blossoms, or beautiful fall foliage. Either way, don’t miss the Japanese-inspired section: super beautiful.

After a morning stroll through the Botanic Garden, pop into the Brooklyn Museum (admission is suggested, so pay as you wish) for a quick perusal. They usually have some cool exhibits, so pick one or two floors to scan.

Visit Brooklyn’s main library and Prospect Park

Walk to the Brooklyn Public Library and marvel at the beautiful architecture and pop your head inside if you wish.

You can stroll through the farmer’s market at Grand Army Plaza just across the street before dipping into Prospect Park for a quick walk.

Hit up Brooklyn’s hippest neighborhood

Next, and head to Williamsburg for the Saturday Brooklyn Flea. I recommend taking an Uber or cab, as subway connections between north and south Brooklyn suck since you have to transfer in Manhattan or take the G train, which almost never shows up except for when you’re entering the subway station and then you’re too late because it’s inexplicably half the length a regular subway car….

Next, it’s time to check out Smorgasburg for lunch. Be sure to get there well before it closes at 4 PM. Smorgasburg is pretty much the birthplace of many Insta-famous food trends, like the notorious Ramen Burger, so be prepared to wait in line and pay a bit more than you’d like. It’s still a worthwhile experience for New York first-timers.

Check out Brooklyn’s thriving street art scene

Now it’s time to walk off all the insane concoctions you’ve put in your stomach. Luckily, some amazing street art isn’t far away. Kent Avenue in Williamsburg has some great murals, and same with nearby Wythe Avenue. For more specific information on where to find Williamsburg street art, check here.

If you’re crazy for street art, you might want to head to Bushwick and see some more of it at the famous Bushwick Collective and more – it’s just a few stops over on the L train. There’s plenty of art you can see just wandering around, but if you prefer more structure, there are also affordable guided walking tours of Bushwick’s street art.

If you’re staying in Williamsburg, you can indulge in a spot of vintage shopping, hipster spotting, and café hopping. Beacon’s Closet is one of NYC’s best thrift stores and it’s fun to peruse some of the tacky wares there. Bedford Avenue, trendy as it is, is also home to countless quality coffee shops (and the delicious Van Leeuwen ice cream truck!) if you need to take a break and rest your feet.

Have a fun night out in Brooklyn

To end the night, you have countless bars are your disposal in Williamsburg and Bushwick — this is pretty much the going out capital of young New York. Night of Joy in Williamsburg has one of my favorite happy hours in all of New York — daily from 5 to 8 PM with $6 delicious cocktails.

A few other favorites include Bar Matchless for a dive bar (also great on Two-for-Tuesday), Berry Park for Manhattan skyline views, and Spritzenhaus for a German beer hall feel.

In Bushwick, I love Heavy Woods and Cobra Club.

Where to Stay in New York

New York is expensive to visit and the fact that it has virtually no off-season doesn’t help. Generally, the season between January-March is a bit slower because the weather is crap but all the Christmas tourists have left. You may be able to find a good deal on a nice hotel during those months, but the rest of the time, New York is expensive. 

Virtually everywhere in Manhattan is pretty well connected, and even neighborhoods like Times Square can sometimes be a surprisingly affordable option at times. If you look outside of Manhattan, there are some deals to be found, but you may spend more of your time in transit than you like unless you’re in waterfront neighborhoods like Astoria, Long Island City, Williamsburg, and DUMBO. However these areas are all quite trendy now, so you might not even save money by staying outside of Manhattan!

Airbnb is an option, but keep in mind that NYC has been hit super hard with an apartment shortage leading to astronomical rent inflation. If you choose to use Airbnb, it’s more sustainable for locals if you rent out a room in their apartment rather than a full apartment, as whole apartments tend to be used full-time as unregulated hotels. Plus you get an insight into the fascinating creatures that are New Yorkers 😉

Budget (around $50 a night): America is notoriously bad when it comes to hostels, and New York is really no exception. I’ve never stayed at a hostel in NYC, but HI New York seems to have the best blend of low budget and high ratings. Chelsea Pods has the best options for single rooms if you prefer a bit of privacy at a low price, but the reviews appear mixed, so do your research first.

Mid-range: For the best savings, check out modern hotels that do away with things like receptionists and concierges in favor of self-check in and other automated systems. YOTEL and citizenM come to mind and both are conveniently located in Times Square which, for all its hecticness, is one of the most central locations for public transportation in all of New York. I haven’t tried a YOTEL property before but I am a big fan of citizenM having stayed at their location in Shoreditch, London, so that would be my personal recommendation if you can afford it.

Luxury: There is basically no end to the amount of luxury options in New York. From classics like The Plaza to newer, more niche offerings like The Library Hotel, you’re spoiled for choice on this end of the spectrum.

What to Budget for New York

Yes, New York is expensive, but it’s not the most expensive place I’ve ever been (here’s looking at you, Switzerland). Here are a few average costs so you can get an idea of what you’ll spend your money on.

A weekly subway pass: $32
A cappuccino at a café: $4-5
Street food and super-cheat eats: $3-5 per meal
Average sit-down restaurant: $15-20 per meal, including tax & tip but no alcohol
A night out: $6-7 for a beer, $8 for a mixed drink or wine, and $10-15 for a cocktail
Average museum entry: $15-20, but keep in mind many have pay-as-you-wish admission

For an average day, I’d budget $30-50 for food (though you certainly can do with less if you research, as New York has a great cheap eats scene, where you can get a full meal for less than $10), $20 if you want to add drinks, $6 for transit, and $30 for activities. That’s $66 to 106 per day — and not even counting the roof over your head!

Depending on where you sleep (and if you’re traveling solo vs. with a partner or friends), you’ll want to add another $50-150 to that total – and that’s on the budget end of the spectrum. I’d say at a minimum, you want to budget $150 per day, but $250 would give you more wiggle room. To extrapolate out to budget for 5 days in NYC, you can expect to spend around $750 but you will be more comfortable with $1250. If you have friends to stay with, though, that will slash a lot of money off your budget.

Reminder: As expensive as New York is, please make sure you also budget for travel insurance on your trip to NYC. I use World Nomads Explorer Plan to cover me on all my trips. It’s inexpensive and can save your butt in an emergency.

In Summary…

So there you have it — my ultimate, 6000+ word plus 5 days in New York itinerary! I’ll stop now before my fingers fall off. If you have a 6th day, I recommend checking out the Bronx — see a game at Yankee Stadium, visit the New York Botanic Garden, or stroll along the real Little Italy along Arthur Avenue. I have a whole lot more ideas covered in my 37 ways to get off the beaten path in NYC post.

I hope you enjoyed this exhaustive, exhausting itinerary to seeing New York in 5 days. It’s taken me nearly two years to feel like I had enough distance from the city to write out a comprehensive guide that I think first-timers, as well as repeat visitors, will enjoy.

If you have any questions about New York, I’m happy to give guidance in the comments!

Read Next: 30 NYC Tips For First-Time Visitors

Note: This post contains affiliate links. That means that if you purchase something using one of these links, I will receive a small commission at no added cost to you. 

28 thoughts on “A 5 Days in New York Itinerary, Written with Love by an Ex-New Yorker”

  1. Newyork is definitely going to my bucket list. Thank you for sharing this. The pictures that you have included are simply mindblowing. Especially the one of Statue of liberty.

  2. Wow, now that is an exhaustive post! However I don’t think there’s any other way you can do a post on a city like NYC! I’ve been twice, the last time being 12 years ago and I would just love to return again. You detail some amazing things I wasn’t aware of when I visited, with great tips on where to find the best street art etc. I’d definitely follow your first couple of days walking routes… And next time I go I can’t wait to see the 9/11 memorial, which was still a construction site when I was last there.
    Unfortunately there was so much I wanted to see in Manhattan, I never got out to Queen’s or Brooklyn, but I’d certainly consider it for next time!
    Thanks for such a great post, and especially for the fab recommendations for food in all areas – those are the tips that come in handy when you don’t know a place! Need to bookmark your post for future reference!

    • Thanks Tilly! Honestly, I think it’s the only way I could write about New York, which is why I put it off for so long. I knew when I finally sat down to write it that it was going to be an insanely long post – it took me over a week to finish writing. I’m glad you found this useful even as a return visitor – I wanted this to be a guide for first-timers as well as repeat visitors so your comment makes me really happy to hear I hit the mark in that way.
      Queens and Brooklyn are definitely not on most first-time visitors’ must-see lists (especially Queens, which never gets enough love) but if you’re a foodie there’s literally no better place in America to eat than Queens. Not to mention food in Queens is often a fraction of the price of places in Brooklyn or Manhattan!
      So happy to hear this was a good resource and that you’ll be keeping it on file for your return visit – fingers crossed it’s soon! Let me know if I can be of any additional help in planning your trip.

  3. Love it! I spent a sleepless weekend in NYC back in 2010 when I first visited it. I’d love to go back and do everything that you have mentioned in your post. 🙂

    • Oh man, if you only have a weekend, no wonder it was sleepless! That’s the New York way, though <3 I hope you get a chance to go back soon. If you ever have it planned, let me know, I'm sure I have even more tips in the back of my mind!

  4. Thank you for this! My husband and I are heading to NYC for 5 days in early June and we will definitely check out some of your suggestions. The first couple days noted are exactly what we are looking for and in neighborhoods we want to explore. We are staying in Chelsea so quite a bit in walking distance or using the subway. Can’t wait. Thanks again!

    • Thanks Melissa, please let me know how it goes (and do let me know if anything changes — this was all true as of when I lived there in 2016 but in New York, everything always changes!!!) Chelsea is a great neighborhood and I think you’ll find it convenient for all you want to see. Do try to check out at least Brooklyn or Queens if you have time!

  5. I never comment on blog posts, but that was such a cool one. I’m traveling to NYC later this week and will follow almost exactly your itinerary. Thanks!

  6. Hi Allison,

    My girlfriend and I are travelling to New York tomorrow (all the way from Tokyo!) and our 7 day visit will heavily rely on this post for inspiration. I just wondered how you’ve considered time in your day scheduling? For example, what time do we start on Day 1 to make sure we’re not rushed and get to enjoy all the sights.


    • How exciting! Some days are longer than others and it all depends on your travel style (do you eat long lunches or grab something quick? are you fast walkers or do you like to wander as you walk?) I’d say roughly this plan is doable on a 10 AM to 6 PM basis with time built in for relaxing… but again, will depend on lots of personal factors, so can’t say for sure 🙂

  7. HOLA!
    We are off to a GIRLS get together, family, sisters in law, to be amazing NYC.
    Your itinerary looks superb. I am not sure which night you think is best to fit in a Broadway Show?
    And the last question, one of my sisters in law asked me about a visit to the best GOSPEL… what do you think?
    hanks for sharing all your knowledge and love for NY.


  8. Hi Allison
    Loved the blog and foodie suggestions!
    My wife, 3 kids under 5 and myself are heading there next year April 2019 for 5 nights and we will get inspiration from you post and probably follow most of it! Ha! Are there any things on itinerary you would definitely avoid with 3 young kids in tow? (And any tips/suggestions)
    We’re also big cheesecake/dessert fans and would love to know you picks on such things!

    The Brisbane Smiths

    • Hi Alan! Hm, there is nothing that is really specifically not kid-friendly. I would maybe not go to some of the museums I’ve recommended as kids can have a short frustration tolerance with museums. I actually don’t have much of a sweet tooth so I’m not able to help you on the dessert front, sadly! I love Steve’s Key Lime pie in Red Hook, Brooklyn though – you can sometimes find it in NYC grocery stores so keep an eye out. Junior’s is everyone’s favorite for cheesecake but to be honest, I’ve never been!

  9. Is this is a walking tour or via subway? I’ve never been so im trying to figure what points need public transport and which are walking

  10. Hi Allison- I just ended 3 full days in New York and used your blog as a basic guide line. Fabulous recommendations- Central park, Staten Island ferry ride, Canal street Chinese food, Smorgusburg, and the flea market were just amazing . I also took the long subway ride to Cooney island and visited the brewery! Thank you for taking time to blog and share your favorites!

  11. Hi Allison,

    Loved this! Just got back from New York and used this as a guideline of where everything is and turned to this when we didn’t know what to do. I don’t know if anyone else has mentioned this, but we actually went to the Brookly Botanic Garden and they sadly are no longer offering free admission on Saturdays! I believe it’s now Friday’s and winter weekday mornings.

    We will definitely try to go back during a spring or summer time! Do you recommend the winter or spring/summer time to go to New York?

    Thanks for sharing your amazing thoughts & for a great experience!

    • Hi Danielle! That’s so great to hear that this was a really helpful resource to you, yay! That’s exactly what I hoped this post would be. I’m sorry to hear that the Brooklyn Botanic Garden changed their hours – I’ll update the post to reflect that. My favorite time in New York is the early fall – no summer crowds and not as humid as summer – after that, late spring (let’s say mid-May onwards) is probably the best season. The summer can be super hot and humid with frequent heat waves, but it can also be really pleasant, so it can be a bit of a grab bag when it comes to summer weather. But if you come from a humid climate you’ll probably be fine in a New York summer (I grew up in California with 115F heat waves, but super dry heat, so NYC in summer is hard for me!)

  12. Hi Allison,
    Me and my boyfriend are heading out to NYC in February 2020 and we’re beyond excited. Your guide has given us so much inspiration regarding things to do and experiencing the real New York! I’d like to ask though, as no doubt we will be bringing back souvenirs/gifts for our families, do you have any recommendations for shopping please?
    Thank you!

    • You’re welcome Nicolle! Hmm, what kind of gifts and souvenirs do you want? I’d suggest the Chelsea Market or Strand Bookstore for shopping in general, but if you have something more specific that you want, I can try to think of something (though I’ve never been a huge shopper!)


Leave a Comment