I’ve hit my 4th-month mark of living in Brooklyn, and close to five years since I first hopped on the Metro-North train from Connecticut to explore New York City on my own.

I remember the anxiety taking my seat each time regardless if it was for a job interview or concert, the knots in my stomach impossible to untangle by the time we arrived at Grand Central. Terrified I’d take the wrong subway to my internship, I would walk the 25 blocks each day (though this was also partly from knowing I’d be stuck in a windowless building all day) until it got too cold. I was always self-conscious walking around the city, worried I’d be judged by the “real New Yorker’s” for my beat-up shoes, or sorry excuse for a backpack.

Now, I’m typing this from the same Metro-North train on my way in for a job, not bothering to look out the window at every pause to “make sure” I didn’t miss the Grand Central station (it’s also the last stop on my line, so why I was ever nervous is beyond me.) I’m wearing a faded green velvet blazer, worn black jeans, and the saddest excuse for flats I’ve ever seen. As we arrive and I head towards the 7 train, I see a woman nervously looking at her map. I’m able to give her directions without thinking twice and don’t miss a beat swiping my Metro card in the process (a true feat for lefties apparently.)

A Highly Practical Guide To Visiting New York City by Jetplane Jean
Bushwick circa 2014

But I’m still learning. Each time I think I have a decent grasp on this beast of a city, I’m flipped upside down. Despite this, I’ve compiled a list of small, yet useful things I’ve discovered during my adventures in the city. Some which I hope anyone visiting New York City will find helpful, whether you’re visiting for the first time, or returning for the two hundredth time. Out of all the things I’ve learned along the way, here are some the things I wished someone had sat me down to explain.


It will always take you longer than expected to get to a place.

Don’t assume that it will take 20 minutes if that’s what Google maps or any other app is telling you, especially during rush hour. Chances are, you will encounter the frustration of not being able to squeeze onto a packed train, or get on the train but have to wait for 15 minutes in between stations because of construction. It’s also pretty easy to accidentally underestimate how far away your destination is from the subway stop. Always give yourself ample time for the subway, Uber, and walking to/from a place.

Skip the cabs & Ubers completely during rush hour.

You’ll be sitting in traffic for quite some time.  The transportation system will get you literally almost anywhere you need to go, plus it tends to be a lot faster during peak times. Better yet, find a new avenue to walk down and do some exploring.

A Quick Guide To Visiting New York City

Let people off the subway before you get on.

This shouldn’t even call for a talking point on this post, but apparently there are a ton of people who do not understand this logic. The train will (usually) wait for you, plus it’s incredibly infuriating when you’re trying to help eager passengers out by exiting, but they’re also trying to shove in at the same time, creating an impassable traffic jam.

Don’t stand on the left side of the escalator.

The left side is reserved for those too anxious/busy/late to stand still and use the escalator the way it was designed. If you need a break, move to the right and allow others in a hurry to pass by.

Walking Around

Avenues run north to south, and streets are east to west.

All of this takes time to get used to, but keep in mind that the street numbers increase as you move north and the avenues decrease from left to right. Broadway cuts diagonal through the city, avenues tend to be a lot wider than streets, and lower Manhattan streets ditch numbered streets in favor of names. Brooklyn has no logic with their street/name placement, quite similar to Boston in that way.

Jump over puddles at all costs.

They’re a lot deeper than they appear and are usually filled with garbage juice from that week’s trash (and god-knows-what else.)

A Rough Guide To Visiting New York City

The absolute best day to walk around NYC is either on a Saturday or Sunday morning.

There’s always a significantly less amount of people out and some streets are filled with a clean laundry smell. People (locals and tourists alike) are usually in bed with a hangover, or using their days off to sleep in. Plan to visit any highly trafficked spots on your list around these times.


Seriously, people will not move for you and you’ve most likely created a huge traffic jam behind you. If you need to text or want to take a photo, either pull off to the side by a building or have a friend guide you along so you don’t get in anyone’s way/get hit by a cab.

You will run into people of every kind trying to get money from you.

Whether it be homeless on the sidewalk, dancers on the subways, or fake monks tying bracelets onto your hands and demanding payment after, there are plenty of people strapped for cash in the city. Know this beforehand and steel yourself for having to say no several times, or give yourself a budget. It’s easy to be convinced into letting go of a couple of bucks more times than you can count and within an hour, you’re already down $50.

City Life In NYC

New Yorkers aren’t rude, they’re just used to things working systematically.

As loud and unpredictable as the city is, it also runs like a well-oiled machine for most of the people who live & work here. This includes learning the perfect timing to weave in and out of people on a crowded sidewalk. Swiping seamlessly at the turnstiles. Having their order and card ready before they get to the counter. It’s overwhelming at times, but taking your time trying to order a coffee or fumbling with change at 8am is a bad idea. People take their morning lattes very seriously here.

A healthy percentage of places are cash-only.

Definitely don’t rely on most bars or restaurants taking debit/credit cards, many places (especially in Brooklyn) are cash-only. It seems ridiculous that an extremely busy place wouldn’t take your plastic, but that’s just the way it is. Plan on taking out cash at your bank before you go to avoid ATM fees.

Pro Tip: Most Bars & Restaurants in Brooklyn are cash-only. Come prepared.

No one cares that you wore your cute heels if they start to hurt after 5 blocks.

Wait until the event or just pack something cute that you can explore in unless you plan on taking a lot of cabs. I promise no one will judge you for your shoes as hard as you’re currently judging yourself.

It gets hotter than Hades and cooler than you’re used to during the winter.

Don’t wear the cute long sleeves during the middle of summer. A lot of places don’t have air-conditioning and tend to be a lot hotter at night with everyone packed in a small bar or restaurant. Bring the jacket in the fall/winter, the wind can tend to be quite brutal as it whips through the tall buildings. Make sure your boots are waterproof in the winter as well as the “snow” tends to turn into a cold, wet mush real quick.

Be yourself.

Don’t get self-conscious walking around. There will always be someone better dressed than you, and someone wearing the full-length neon puffy jacket. Relax, dress for yourself, and don’t be afraid to try out that wild outfit you’ve been nervous about ever since you bought it. This is the perfect city to let your true self shine.

Avoid cabs during rush hour. A Quick Guide To NYC


Mind your things.

Don’t put your phone in your back pocket or assume your drawstring bag is safe. There are people who are constantly looking for those disheveled, mindless tourists. This doesn’t mean you need to wear your backpack on your front, but stay aware. Do not think anything is safe for even a second. If you have to put something down, stand with it in between your legs or stand on a strap so it can’t be easily snatched when you’re taking a photo.

Use common sense when going out.

New York City has recently become a lot safer, but the same common sense rules apply. I’ve had friend’s drinks spiked, purses stolen, and seeing men unable to no for an answer. Like your mother told you, keep an eye on your drinks, go out with a friend, and don’t be afraid to let the bartender or another group of girls (or basically anyone really) know if someone is bothering you. New Yorkers will take care of you if you ask.

A Quick And Useful Guide To Visiting NYC

Know your route home.

Make sure to double-check your subway line before you head to take make sure it isn’t under construction and shutting down early. If you do walk home, avoid the dark side streets as well as walking along or through parks. Stick to the busy, main roads for as long as possible or take an Uber.

Take precaution around the unsavory.

There are people who like to draw attention to themselves by screaming or making a scene one way or another. It can be hard to not get distracted by this, but keep your focus on moving away from them as quickly as possible if you can help it. Distractions like that are used all the time to take your valuables, my phone was stolen while trying to get off the subway when two men carrying surfboards in the middle of January made a massive distraction. Or sometimes they’re simply people looking for trouble. Stay aware, but avoid eye contact if/when possible.


  1. The only excuse for being late is the damn G train, otherwise you’re expected to arrive 5 minutes early to everything to be considered on time.
  1. I will come and personally rip the Olive Garden bread stick from your hands. There are thousands of amazing eats in NYC, go find one to tell mom about!
  2. Not all $1 pizza stands were created equal and I’m not going to tell you which is the best. Come back and comment which was your favorite.
  3. The best place to use the public bathrooms is midtown/flatiron section. Think Starbucks and fast food places.

A Practical NYC Guide

What did you think of this quick & practical guide to NYC? Are there any tips you’ve learned along the way that you’d like to share? Are there any areas you’d like me to expand on in another post? Comment below!

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