Last updated on December 31, 2019
Preparing for your first trip to the Big Apple? Here’s my beginner’s guide to New York City, complete with advice on essential things to do (and not to do), and a few pointers on where to eat and sleep.
You’re going to love your first time in New York. You’re also going to be immensely overwhelmed by it.
But keep these tips handy and you can be sure to dig a little deeper under the skin of the greatest city on Earth.
1. Don’t be cocky like me a think you can see all of New York on your first visit
I know this tip is featured in every travel guide on ‘what not to do in New York’, but, really. It’s impossible not to underestimate the scale of New York City. Each borough is basically the size of an entire city, and everything takes longer to see and explore than you’d think.
For example, it takes at least an hour to walk from one end of Central Park to the other, and that’s only if you know where you’re going and hike at a steady pace.
Walking across Brooklyn Bridge: the best part of 30 minutes, more if you stop for photos.
And although the subway is relatively easy to navigate, it can still take a lot of time and energy to work out where you’re going.
If you’re visiting New York City for a few days or a week, you’ll probably want to stick to just two or three neighbourhoods maximum. Any more and you’ll just exhaust yourself and, in my case, not see much of the neighbourhoods that you do visit.
2. Orientate yourself at the Top of the Rock (epic panoramic skyline views of New York)
I’m not one to pay for panoramic views, especially when there’s no rooftop bar involved, but the ‘Top of the Rock‘, located on the 70th floor of the Rockefeller Centre, really does offer the best views in New York.
You can see over Central Park, the Empire State Building, Downtown Manhattan, The Chrysler building, One World Trade Center, Brooklyn Bridge in the distance, and more. It’s insane.
Go here on your first day for that “Holy sh*t, we’re in New York City!” feeling.
Tip: Visibility is paramount. I’d suggest getting this flexible ticket option (roughly $40), which allows you to schedule your visit around the weather. I wish I’d gone for sunset, but keep in mind that this is the busiest time.
Alternatives panoramic viewpoints in NYC: The Empire State Building’s observation deck (same price) is another popular spot (although then you obviously you won’t have the city’s most iconic building in your photos). The New York One World Observatory (a couple of dollars cheaper) (on the 102nd floor of the new World Trade Center) is another great option and is billed as ‘the tallest building in the Western Hemisphere’.
Free alternative viewpoint: Want skyline views of New York without having to fork out forty bucks? I don’t blame you. I was tempted by the Rainbow Room Bar, which is located on the 65th floor for Rockefeller Centre. It’s not “free” exactly, as you’ll need to order something, but you should be able to get a cocktail or two for $40 and the views are pretty damn inspiring. Definitely a good spot for a sundowner tipple or three!
3. Dedicate a whole day to Central Park
Well, maybe not a whole day, but keep in mind that the sprawling green lung of Central Park is not, as I’d imagined, the sort of park you can stroll around in 20 minutes or so on your way elsewhere.
It’s vast and there’s just so much to explore!
What to see and do in Central Park:
Get lost in The Ramble – which might as well be a forrest in the middle of nowhere.
Watch an amateur baseball game on The Great Lawn – which I actually enjoyed even more than my visit to Yanky Stadium (more on this to follow).
Pose for photos on Bow Bridge – a beautiful leafy scene that I’m sure has featured in a movie or two.
Gasp in awe as I did when you discover Belvedere Castle – (not a Disney-esque castle as I’d imagined, but a full-size bloody castle!).
Enjoy a dinner to remember at The Loeb Boathouse – I didn’t do this as it seemed silly on my own, but I heard a couple of people raving about it).
Catch an outdoor concert or theatre performance at the Delacorte Theater – a pretty dreamy place to be on a sunny summer’s evening.
Tip: After my first blister burst as a result of my rushing around trying to see as much of the park as possible, I started wishing I’d done as so many other (more clued up) people had done and rented a bike (grab one for $8 here). If you want to make sure you see all of Central Park’s best bits then you may also want to join a bike tour like this one ($33). If you’d prefer to walk, then perhaps consider joining a walking tour like this one ($20). There’s definitely enough to see and learn to warrant joining a tour.
4. Take in a ball game at Yankee Stadium or the Mets’ Citi Fields
More than walking around Central Park or eating hotdogs, seeing a ball game at Yankee Stadium was the one thing I simply had to do during my first visit to New York City.
I’m not a big sports fan, mind you, and have no particular interest in baseball. But I just can’t think of a better way to experience New York than by going to see a ballgame and enjoying all the nonsense that goes along with it.
Tip 1: A few people told me it would be all but impossible to find tickets to Yankee/Mets games and that, if I did, they would be extortionate. However, I had no problem whatsoever finding tickets for both Yankee Stadium and the New York Mets – for less than $20 a pop. Just be prepared to pay more or less the same price, if not more, for a beer and a pack of peanuts!
Tip 2: Part of the ritual of seeing a ballgame in New York is going for a couple of pre and/or post game beers. Popular bars near Yankee Stadium include Stan’s Sports Bar, Yankee Tavern and the Bronx Draft House. I also liked the Dugout (proper divey!).
Tip 3: Yankee Stadium is located right in the heart of the Bronx. It might be known as one of New York’s most dangerous neighbourhoods, but in my opinion it’s also one of the most interesting and authentic. Take a quick stroll after watching a game and you’ll get a sense of just how cosmopolitan it is. Latin Americans playing cards and dominoes in the streets, cooking up barbecues right on the sidewalk. Excellent street food, great little delis and international supermarkets selling food from all over the world. The Bronx is also home to the “proper Little Italy”, apparently.
5. Work out your daily budget, then double it…
As a Brit, I’ll never get used to America’s tipping culture.
The idea of having to leave a “customary” 20% tip (that’s the minimum apparently) for good service seems entirely counterproductive to me.
In fact, I encountered overtly rude customer service at a couple of the dive bars (although in a strange way I think it’s all part of the whole experience), and I was still expected to leave a dollar tip per drink.
A $5 beer suddenly becomes a $6 beer. A $12 burger suddenly costs $15.
But of course you only tip at bars and restaurants, because pouring a pint or taking the cap off a beer bottle is so much more arduous than making a sandwich in a deli or scooping an ice-cream together for you (where you aren’t expected to tip).
Anyway, tips aside, everything in New York costs more than you’d imagine. I treated myself to a lonely dinner in Little Italy. I had a bowl of spaghetti with meatballs and two beers. It cost me $50 (and it was only that cheap because I left a crappy tip and then legged it). I asked for a glass of house wine: “I gotta Pinot Grigio. $14.” No thanks!
You can’t really walk into a bar or pub in New York without spending $20. Lunch will be at least $30. You soon understand why everyone eats at fast-food outlets all the time (where you don’t need to tip, which seems peculiar to me as they clearly work just as hard).
But there is a solution…
6. Snack on pizza and save the big bucks
What could be more “New York” than chomping down a few slices of fresh pizza?
Everyone’s at it, from Wall Street tycoons to rough sleepers and everyone in between. In fact, there’s probably no better place to get an overview of the Big Apple’s residents.
And the good news is that, in New York, pizza is all about eating cheap!
There are countless ‘pizza by the slice’ joints around the city. The idea is simple: they offer a classic cheese slice for a dollar, which they serve fresh, hot and fast. This is great way to eat quickly and cheaply on your way between different sights and landmarks (or en route between dive bars).
7. Tour New York’s historic dive bars
Character. Chops. Contact. That’s what you get at a good ol’ fashioned dive bar, and New York’s full of the buggers!
You’ll know them when you see them. They’re the ones covered in crusty old stickers and sloppy graffiti. They’re the ones illuminated with flickering beer-branded neon signs.
They’re the ones with surly service and handwritten notes pinned up behind the bar that say: “Don’t bring your self-entitlement here!” and “If you’re asking what the cheapest thing in this bar is, it’s probably you!” and “Cash is King!”
The music on the jukebox is always too loud. They have pin ball machines, sports on multiple TVs, and the bartender is typically more interested in doing shots with the regulars than serving you.
Ah, they don’t make ’em like they used to.
You’ll find New York’s best dive bars scattered throughout the city (Alphabet City is a good area to start in), but a few of my personal favourites include:
The Library (East Village, Manhattan) – Rock ‘n’ roll jukebox and 2-4-1 happy hours!
Turkey’s Nest (Bedford Ave, Brooklyn) – Neon lights, lively locals and sports on TV!
Horseshoe Bar (aka 7B) (East Village, Manhattan) – Iconic dive bar you’ll recognise from many a movie.
McSorley’s Old Ale House (East Village, Manhattan) – Not really a dive bar but the oldest and coolest Irish pub in New York.
Tip: Go a little earlier in the day (these places are all about midday drinking so don’t feel self-conscious) to make the most of the happy hour offers.
8. Stroll The High Line for local vibes and scenic views
Something of a newcomer to New York, The High Line is a leafy park that sprawls out along an abandoned railway line for almost two miles.
The views over the city are fantastic and you get a real sense of the area’s community spirit.
Families play. Couples canoodle.
Tip: From the High Line it’s only a 10-minute stroll down to the Hudson River Park. Head for Pier 63 and stroll southward along the river from there…
9. Stroll the Hudson River Path down to Pier 46
If like me you travel because you are curious about how other people live their lives, especially in iconic places like New York, then I would highly recommend taking a sunset stroll along the Hudson River Path.
I walked all the way from Pier 63 to the World Trade Center (stopping at Pier 45 along the way) and, for the hour it took, I felt part of the city.
I eavesdropped on people’s conversations as they strolled and jogged past me.
They said things like:
“Now he’s married a thirty year old! And you think she wants a baby?”
“I thought I’d got outta this, but here I am again.”
I watched the dog walkers and paperback loungers, heated basketball games and little league training assaults.
I spotted quite a few nice looking cafes, bars and restaurants along the way (City Vineyard at Pier 26 looked lovely).
Tip: If you don’t have the time or energy to walk all the way from Pier 63 to the World Trade Center, stop at Pier 45 to enjoy the stunning skyline views before cutting back into the city to explore Greenwich Village. You can also rent a bike nearby and see more of it in less time.
10. Forget Sex in the City and pack as if you’re going hiking in the Andes
OK, OK, maybe that’s a little hyperbolic, but it needs to be considered.
We’ve all seen the films and TV shows, but your first trip to NYC will feel more like an adventure hiking holiday than a day out with Carrie Bradshaw and her bitches.
You’ll want comfortable clothes and shoes, and a good backpack/bag to carry a water bottle and, ideally, a phone charger so you can ensure you alway have Google Maps at hand.
11. Explore beyond Manhattan…
“Most travellers just stay in Manhattan the whole time,” said pretty much every local New Yorker I met.
I know I started this post off by saying not to try to see too many boroughs, but I do think it’s definitely worth getting out of Manhattan for at least one day (or two if you’re staying in New York for a week or so).
A few suggestions…
12. Eat your way around Queens
“We live in New York, in Brooklyn, but even we’ve never visited Queens before,” said Nigel and his wife when trying to explain why they were so impressed I was exploring the area on my first trip to the city.
I met them on Culinary Backstreet’s fantastic United Kitchens food tour, which is a cultural and gastronomical deep dive into the area’s various ethnicities.
Queens is celebrated for its rich cultural diversity, which makes it one of the most fascinating places to eat in New York.
One minute we were eating handmade tortillas at a local Mexican restaurant, the next we were exploring Argentinian and Columbian fast food, Chinese dumplings at food trucks, and heading to a Thai grocery shop for dessert.
It was easily one of the most fascinating food tours I’ve been on (and I’ve been on more than most).
Great to be shown around by local guide Esneider, who has lived in the borough since moving there from Columbia over 20 years ago.
If you’re interested in food and culture and want to dig a little deeper into the real New York beyond Manhattan and Brooklyn, definitely consider joining this Queens food tour.
Speaking of exploring cool neighbourhoods beyond Manhattan…
13. Spend as much time as possible in Brooklyn
It’s funny, I think, without realising it, I had a pretty clear vision of what I imagined New York would look, smell and sound like (based on books I’ve read, films I’ve watched). But it was only when I got to Brooklyn that I actually found it.
I love Brooklyn’s leafy residential streets, all lined with rows of old brownstone buildings. I love the ancient corner cafes and trendy bars that line Bedford Avenue.
There were film crews everywhere, turning whole streets into film sets, and beautiful young things fluttering from bar to bar, restaurant to restaurant.
Tip Top Tip: If you’re interested in architecture and want to explore Brooklyn with a local, I would highly recommend taking Context Travel’s Brooklyn Walking Tour, which includes a walk over the emblematic Brooklyn Bridge and guided tour through DUMBO, along the river and into the heart of Brooklyn. Our guide Irena was extremely knowledgable (a professor at New York’s prestigious Columbia University no less) and was in fact born and raised in Brooklyn itself, so it’s fair to say she knows quite a bit about it.
Talking of tours…
14. Take tours to connect with locals and maximise your time
The moments that really meant something to me during my time in New York were the moments where I got to connect with real New Yorkers.
They’re not as hostile as we’ve been led to believe and are generally pretty open and honest about their beloved city.
And from experience, I’ve found that one of the best ways to connect with locals is to take a tour with a local guide. I had a fantastic time on the Grand Central Indoor Food Court tour with Nancy from Manhattan Walking Tours, and two lovely couples who were travelling from Canada.
Nancy introduced us to the staff and specialities of each stall while regaling us with fascinating stories and facts about the colossal building itself, which cost something like two billion dollars to build in today’s money.
As well as various nibbles throughout, the tour also included a traditional bowl of clam chowder at the iconic Grand Central Oyster Bar & Restaurant, which was a definite highlight for me.
But what I liked most about hanging out with our guide Nancy for a few hours was simply learning how she talked about the city. She’s a born and bread New Yorker and loves it for everything it is (and isn’t). I loved hearing the way she located everything in the city by street numbers, “Oh, yeah, you should go to between 28th and 6th,” she’d say.
15. Skip Times Square
OK, I fully understand you’ll want to see Times Square. I get it, it’s a “must”. But for the love of God, don’t waste any more time there than you have do.
Personally I found it a bit of a huge let down. It clearly only exists for tourists, and even I managed to get scammed/coerced out of €20 by the infamous hip-hop CD bullies (I’ve honestly never felt so violated or stupid).
If anyone stops for a friendly chat, or to “give” you a copy of their new album, you can safely it’s a scam. Don’t stop walking, and don’t take anything from anyone.
Talking of skipping things…
16. Skip the Statue of Liberty
I know, I know, the Statue Liberty is the Eiffel Tower of New York and I fully understand why you would want to see it. But…
Keep in mind that, to take a boat all the way to the island (with a million other tourists) and then do a tour or climb the stairs tot he top of the statue, you’ll need a good 5 or 6 hours all in all.
Much of this time will be spent on a boat or waiting in line (in the burning heat or whipping wind), and the crappy food on the island (this is the ultimate tourist trap after all) will cost you a small fortune.
If you have the time and really want to see it, then of course go for it. But, if you want to make the most of your time in New York and think you could see/do more with those 5 or 6 hours, well… don’t be afraid to give it a miss.
Mega tip: A great alternative (as recommended to me by every New Yorker I asked about whether or not it’s worth visiting the Statue of Liberty): hop on the FREE Staten Island commuter ferry which zips back and forth between Whitehall Terminal on the southern tip of Manhattan to Saint George Terminal on Staten Island. The ferry doesn’t actually stop at Liberty Island, but the views of the statue as you pass it are epic.
17. Eat beautiful burgers at Shake Shack
Shake Shack isn’t exactly a secret, but it is something of a life saver for hungry travellers who want to eat well without spending $50 on a burger and a beer (which is what I was paying all too often).
Shake Shack is to New York as In and Out is to California: a burger joint chain that’s extremely popular among travellers and locals alike.
The burgers are seriously good and, the best news of all, they also offer a range of craft beers too.
In a nutshell, Shake Shack is an affordable indulgence that you can also justify as an “essential New York foodie experience”.
Make it Happen
When to go to New York for your first visit: I think any time is a good time to be in New York, but remember it can get pretty icy in winter and ridiculously hot in summer. I’d suggest late spring or early autumn.
Don’t forget you ESTA visa: Don’t be a plonker like I was on my first trip to the USA and forget to sort out your ESTA visa, which you need to enter the country. It’s simple and straight forward to do, but it’s not something you want to be stressing about at the airport (such as I did).
I also highly recommend paying close attention to where you make your ESTA application, as on this particular trip to New York I made the mistake of paying over $100, which is ridiculous as you shouldn’t have to pay more than $30 to so. I also managed to write my passport number in wrong, which meant my ESTA wasn’t even valid when I got to the check-in desk. A very stressful 30 minutes ensued, whereby I had to reapply using my phone and extremely shaky/nervous hands and then hope my application was accepted in time for me to check-in, get through security and board the plane. I made it with a few minutes to spare in the end. Moral of the story, make sure you take care of it properly long before you get to the airport.
How long to stay in New York on your first visit: You’ll want at least 4 or 5 full days, so I’d suggest booking 5 or 6 nights minimum.
Airport transfers: Be sure to book a shuttle bus (around $12 per person) ahead of time as it’s all a bit chaotic at the airpot.
Where to stay in New York during your first time in the city: There are literally thousands of great accommodation options in New York and the only real challenge is trying to work out which are you want to stay. Generally speaking, the best area to stay in in New York on your first time is Manhattan, as it’s simply the most central and convenient place to be. Anywhere in Manhattan would pretty much do the job, but I’d probably recommend Downtown Manhattan or Midtown Manhattan, which are home to the following areas:
Downtown Manhattan: Greenwich Village, East Village, SoHo, NoLita, Little Italy, Chinatown, Lower East Side, Tribeca and the Financial District
Midtown Manhattan: Midtown Manhattan: Hell’s Kitchen, Midtown East, Times Square, Bryant Park, Chelsea, and the Flatiron District.
Great value 3-star hotels (from around $100 a night)
The French Quarters – beautiful boutique in Hell’s Kitchen that “evokes a New Orleans-like feel”.
Hampton Inn Manhattan, Times Square South – comfort and convenience in Hell’s Kitchen.
Hampton Inn – great value and location, just footsteps from Madison Square Garden.
Element Times Square West – sleek and stylish 3-star in the T
Great value 4-star hotels in Manhattan (from $150 to $200 a night)
Walker Hotel – spectacular boutique in Greenwich Village with a 1920s-inspired décor.
Crowne Plaza HY36 Midtown Manhattan – gorgeous hotel in Hell’s Kitchen with great dining and leisure facilities.
The Bryant Park Hotel – serious style in a prime location overlooking Bryant Park (and New York Public Library).
Hotel 50 Bowery NYC – highly rated property in an ideal location in Chinatown.
InterContinental New York Times Square – no introduction needed.
The Roxy Hotel Tribeca – the perfect ‘hip hotel’.
Broadway theatre tickets: Find great deals and book on your phone here.
Hop-on-hop-off bus: Get your tickets here.
New York City Explorer Pass: Get huge discounts on museum visits and more.
Overheard in New York City (September 2019)
“They don’t feel safe anymore. Like, that kind of thing.”
“My straw’s not working anymore! Fucking straws!”
“I can’t tonight. I’m going to dinner with my psycho roommate.”
“Larry has no choice. He’s got alimony up the kazoo.”
“It’s funny you ask… I actually have 12 servants of that race.”
“I love strangers.”
Note that I attended some of the tours mentioned in this post as a guest, but all opinions and tips are all my own.