Sometimes, you go to a city for the first time and you’re left completely underwhelmed. What was everyone else talking about? You clearly aren’t seeing the same things. It’s true that some destinations can’t live up to the hype of what you see online. Sometimes, though, it’s the travel mistakes that we make which detract from our experience. The first time I went to New York City, that was me. I was there for work, which factored into the lack of dazzle and appreciation. My time was mainly spent working ridiculous hours (both time of day and length). I only got to see Times Square as we had to walk through Times Square to get from our hotel to where we were working.
However, when I returned on another work trip, I had learned from a few of my initial mistakes and had a much better time. It wasn’t New York’s fault that I made a few mistakes that took away from my enjoyment.
So this article is to make sure that you don’t do what I did. Read on to craft your perfect first time in New York or check out this one-day itinerary for some extra help.
Staying In The Restaurant Comfort Zone
New York City has so many familiar franchises and it might be tempting to stick with what you know. On my first trip, I was with coworkers who weren’t very adventurous, which meant that the majority of our meals were at places you could eat at anywhere else in North America. We wound up eating at a lot of chain restaurants. When we did venture somewhere new, they didn’t want to try anything adventurous off the menu.
As a result, it left me feeling a bit lacklustre about the food scene. It’s purely because I didn’t get the opportunity to try more things. In later trips, I was able to go to more restaurants, bars, and great hotspots, but it took more than one trip.
If you’re headed there for the first time, do a little research first to find those amazing holes-in-the-wall and the places you don’t want to miss. Don’t be like me and make these first-timer NYC travel mistakes.
Not Using The New York City Subway System
Walking is a fantastic way to get around New York City. The grid system makes it really easy to understand where you’re going, but keep in mind that if you’re going between 1st and 12th Avenues, the distance is much longer. If you’re on the streets, they’re really short and you can conquer dozens of them easily.
That said, New York City has one of the best subway systems available and you should take advantage of it. Nowadays, you don’t even need to buy a metro card (unless you want one for a souvenir). You can simply tap your credit card at the turnstile to get access!
If you have limited time in New York, take advantage of the metro. Walking is fabulous and easy if you’re able, but it takes a lot longer. Time is money, especially if you’re only there on a short trip.
Ignoring the Cultural Experiences
Cultural here has a lot of meanings, but when I use it, I just mean to say that there are so many museums, experiences, and moments that you can do that aren’t just seeing neon billboards or going shopping on Fifth Avenue. Balance is the key, so when you’re in New York, being able to have a little of the flashy and shopping and then a bit of culture (like visiting the Met or MoMA or one of the lesser known museums) is the way to go.
Staying in the immediate Times Square area
New York is a compact city that you can walk around with ease, but that doesn’t mean you should stay in the immediate Times Square vicinity. I’m not going to say you should fully avoid it because it’s still an experience to overwhelm the senses, but once you’ve done that, head elsewhere. The prices will be cheaper, you’ll get more options for non-chain restaurant food, and there’s so much more to see. Times Square is good for passing through, in my opinion, but don’t let it anchor you down on your trip.

Paying Full Price for Broadway shows
There is an exception to this mistake. If there’s something on Broadway that you absolutely must see, then don’t leave it to chance. There have been productions that I made whole trips out of. In those cases, yes, buy the full price tickets. If you don’t care what you’re going to see, that’s when you should avoid the mistake of paying full price.
Instead, take advantage of TKTS booths or even online options. You can find alternative options for your tickets in this post: Headed to Broadway? Don’t pay full price for tickets!
Not Preparing for the Weather
It’s true that weather is fairly unpredictable everywhere, but New York City is its own beast. Given that it’s a concrete jungle, it can trap heat in the winter in a way you might not expect. It can also be warmer than you might anticipate, damper, or cooler. The lesson here that I learned is to prepare yourself and bring layers so that you’re ready for the weather no matter what.
(Sidenote: You should also remember what you brought with you. I took off a pair of fingerless gloves on a bus because it was warmer, but then absolutely forget them there. Keep your layers on your person at all times and don’t be like me!)
Don’t Be Afraid to Improvise
Don’t stick to your plan too tightly. Some of the very best moments I’ve had in New York weren’t the intricately planned affairs. One amazing example is after a concert in Brooklyn, I decided that I wanted to get off and see the New York City skyline at night. Not only was the view incredible, but only a few other people were there. It all just meant jumping off the subway as a last minute thing. This also goes for finding new restaurants and trying new things. Sometimes, not planning every moment is the best way to experience New York — and here, I speak from experience.
Hopefully you’ve got a game plan now to avoid all the travel mistakes that I made. New York City is an incredible place to visit. Take advantage of these tips and you’ll have a vacation to remember!
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