7 Mistakes I Made in New York City – So You Don’t Have To

After visiting New York City for the first time in 2015, I was convinced our second trip in May 2022 was going to be much better. After all, we had learned a few things!

We weren’t travelling in the depths of August humidity, we had pre-booked important tickets and we weren’t going to let hanger (hunger + anger) get the best of us.

But despite all that learning, we still managed to make a lot of mistakes in New York City! So, to save you from making the same errors we did, I’m sharing seven mistakes I made in New York City.

Of course, despite all of the mistakes, we still loved our trip to NYC! And we didn’t mess up on everything. Scroll to the end of this post to check out seven things we got right in New York City!

This post was updated in October 2026

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NYC Mistake #1: Messing up our subway trips (more than once!)

As someone who grew up in Toronto, riding the subway since before I could walk, I pride myself on understanding public transportation. And yet, we just kept messing this up in New York!

It started at the airport when we couldn’t figure out where to buy MetroCards. Then, after finding the one machine that sold them, we didn’t understand that you needed to validate them before getting on a bus.

Luckily on our 2026 New York trip, this was no longer a problem as we could simply tap on with our credit cards. Hooray for using our phones as an easy way to stay connected in NYC!

The next day was worse: The subway line we were meant to take into Manhattan wasn’t running in that direction.

But instead of walking to a different line (like Google Maps told us to!) we got on in the opposite direction, rode a bunch of stops out of the way, waited on the platform for 10 minutes, and finally got on a train in the right direction. We wasted about 30 minutes just to get back to where we started!

And the subway woes didn’t end there. After every subway snafu, we swore we’d get it right the next time. And in our defence, we never made the same mistake twice. But we sure did make a lot of subway mistakes!

We entered a subway station through the wrong entrance, not knowing we wouldn’t be able to cross over to the other side. That caused us to get lost and locked out of the turnstiles. Another time, we got on a train in the wrong direction simply because we didn’t read the signs closely enough!

Despite all our subway mistakes, I still highly recommend the subway for getting around New York. Just pay extra attention to signs, closures and the directions GoogleMaps gives you!

NYC Mistake #2: Trying to eat anywhere near Times Square

On our first trip to New York City, we made the mistake of eating at a tourist trap near Times Square: an overpriced Italian restaurant with awful decor and even worse food.

This time, I knew better. Beforehand I looked up a number of restaurants within walking distance of the Broadway theatres that, despite their closeness to Times Square, were not touristy, expensive or just plain bad.

The issue? Apparently these unicorn restaurants are not actually that secret. In fact, almost everyone in Manhattan seems to know about them.

Every place on my list was horribly lined up and packed with people. And with not much time before our show started, we couldn’t afford to wait for a table.

So next time, I’m making a reservation or planning to eat in another part of Manhattan before transiting into Times Square just before showtime!

NYC Mistake #3: Not dressing correctly for the weather

The worst part of our first trip to New York City in August 2015 was the disgusting heat and humidity. This time, we were visiting in May and assumed the weather would be perfect. Sadly, it wasn’t. And we were not prepared.

On our first day in New York, it poured. Luckily, we had thought to bring rain jackets. But we weren’t ready for a monsoon!

After an outdoor walking tour with the 9/11 Tribute Museum, my rain jacket was so soaked through that my underwear was wet! I ended up throwing out my (not-so-waterproof) jacket, and buying a cheap umbrella (that was no match for the wind) and a cheap sweater to try and keep warm.

The next day, we headed out to Liberty Island to see the Statue of Liberty up close. For some reason I didn’t think that being out on a boat and then on an island in the middle of the Hudson River would be windy. But of course, I was wrong.

It was insanely windy – so windy that our tour guide had to move us behind a shelter because we couldn’t hear him speaking over the wind. And, of course, I wasn’t wearing a jacket!

You would think coming from Canada, where it’s cold, and from Vancouver, where it rains constantly, I would be better prepared for cold and rainy days in New York City. Apparently not!

Luckily when we returned to New York City in September 2026, I was more prepared. I wore waterproof shoes and a proper jacket and stayed dry!

NYC Mistake #4: Not spending enough time exploring different neighbourhoods

One of the things I love most about New York City are all of the different neighbourhoods.

Unlike some cities, where’s there’s just one area where things are happening and everything else is suburbs, there are so many cool pockets of New York. And every pocket seems to have it’s own distinct style, with unique houses, shops and restaurants.

But sadly, we didn’t get to spend nearly enough time exploring any of New York’s neighbourhoods on this trip. We didn’t make time to stroll down streets, visit different parks and just discover cool restaurants or shops along the way.

Criminally, we didn’t even make it to Brooklyn! (Though, we did visit Brooklyn in 2015.) Next time, I definitely want to prioritize exploring neighbourhoods over hitting a bunch of tourist hot spots on a scavenger hunt around Manhattan.

Apparently I didn’t learn from this mistake well enough, because our 2026 trip saw us once again sticking to Manhattan. We even stayed at a hotel in Midtown, so really didn’t venture too far from the tourist crowds.

NYC Mistake #5: Eating at the wrong places

New York City is known as the food capital of the world. In planning our 2022 trip, I saved 183 places to eat in New York on Google Maps. And for our 2026 trip, I went even wilder with over 600 places saved!

And while we did have a few phenomenal meals on this trip (check them out below in the list of things we did right!), we also wasted a few at less than stellar places. And on such a short trip in such a foodie city, every wasted meal felt like a huge travel sin.

On the day it poured rain, we sought refuge in the Oculus and ended up eating in an underground food court. The food was fine, but who goes to New York City to eat at a food court?

And on the day we visited the Met, we were desperate for a break and in need of a refuel so hit up the overpriced and mediocre Met Eatery.

Next time, we plan the New York City itinerary around where we want to eat!

NYC Mistake #6: Not having enough stamina for the museums

I will admit that I am not a huge museum person. I can usually do about an hour of intense interest in a museum before I’m dragging my feet and staring longingly at the museum cafe.

Two hours in and I’m pouting, stopping at every bench and eyeing the exit. Don’t even talk to me at the three hour mark.

But New York is a city known for its excellent museums! And even though I found the museums we chose to be super interesting, I just couldn’t keep up my stamina to explore them thoroughly.

On our first day, we visited the 9/11 Tribute Museum, which is not the same as the giant museum located at Ground Zero, the 9/11 Memorial & Museum. The Tribute Museum is a few blocks away and more focused on survivors and first responders telling their stories.

I loved the Tribute Museum but wondered if we were missing out by not going to the Memorial & Museum too. But by the time we finished with the Tribute Museum and tour, I didn’t think I’d have the mental or emotional capacity to take on the another museum.

Fortunately, we did make it to the 9/11 Memorial & Museum on our 2026 trip and it was well worth the visit. Sadly, the 9/11 Tribute Museum closed its doors in late 2022, so I’m glad we had a chance to tour it when we did.

On Ellis Island, we loved checking out the Immigration Museum and seeing how migrants to the US arrived by boat.

But after about an hour with the audio guide, I was losing steam. We rushed through the modern immigration sections, barely poking our head into the exhibit on the first floor, before we needed to catch our ferry back to Manhattan.

Similarly at the Met, we left many wings of that giant museum untouched. And even in the wings we did visit, we barely scratched the surface of all of the incredible information, art and artifacts inside.

While there’s easily a full day’s worth of things to see at the Met, after a few hours all I wanted was a coffee on a bench in Central Park.

NYC Mistake #7: Only spending 3 days in New York City!

By far, our biggest mistake in New York City was only spending three full days there. Luckily, we had visited before, so could leave some items off of our itinerary. But New York is a place you could spend a whole year and still not fully discover.

With only three days, our trip felt rushed and exhausting. We woke up early each morning to get to our first activity and arrived back at our hotel late each night.

And while I’m glad we didn’t waste any time in such a cool city, it’s hard to come back from a vacation feeling like you need another vacation!

Unfortunately, with Colin’s limited vacation days, we could only get three full days in New York City for this trip. Making it worse, we decided to prioritize budget over time and take connecting flights.

With delays and extra time to get through security, we spent about 12 hours just getting there (and another 12 getting back). I ended up getting sick on the flight home, making the experience even rougher.

While I’m sure no trip to New York ever feels long enough, three days (plus two full days of travel) felt really short. We missed out on so many great restaurants, museums, parks and neighbourhoods.

In 2026 we got five nights in New York (and took direct flights), which felt like a good amount of time but I still wanted more. My dream would be to spend a month or two living in New York and actually getting to know some of the local areas better.

7 things I got right in New York City

Despite the seven big mistakes we made above, we still had an awesome time in New York City! And we did manage to get a few things right.

1. NYC Win: Buying Broadway tickets from TodayTix

I am a huge musical theatre fan – that’s how we ended up seeing four shows in three days in New York City! And TodayTix was how we made that possible.

Instead of lining up at the TKTS booth in Times Square or buying full priced tickets, we were able to get discounted tickets through the TodayTix app. We also were able to score rush tickets to two shows – seeing them for a discount in great seats!

In case you’re curious, the four shows we saw were: The Islander, American Buffalo, Dear Evan Hansen and Six. Six was absolutely incredible, so much fun and I couldn’t recommend it more (though sadly it’s closing in Jan 2027).

On our 2026 trip, we turned to TodayTix again, scoring tickets to Schmigadoon and Two Strangers Carry a Cake Across New York with their theatre sale.

2. NYC Win: Getting a MetroCard & taking the subway

Even though we messed up taking the subway almost every time, I still highly recommend taking the subway when visiting New York City.

Not only will it make you feel like a real New Yorker, but the subway connects almost everywhere you’ll want to go and is often much faster than driving (no traffic!). It’s also really affordable.

We opted for the unlimited 7-day pass which I think we made use of, even though we were only there for three days/four nights. In 2026, we took the simple route of just tapping our phones to pay, which worked great!

3. NYC Win: Staying in Queens

Staying in Queens was perfect for our short trip to New York City. Our hotel, Lotus BLU Inn & Suites – Long Island City, was an easy subway ride into Manhattan, but we were able to save a lot of money by not staying directly on the island.

We were also much closer to LaGuardia, which is the airport we flew in and out of.

If you can’t afford to stay in Manhattan, definitely check out the surrounding boroughs. My advice is to make sure you’re on an easy subway line into the city, if that’s where you plan to spend most of your time.

I know a lot of people stay in New Jersey, but I’ve heard the train into New York City can get expensive. You don’t want to spend more money commuting than you would on a closer hotel!

You’ll also want to factor in which airport you’re flying in and out of. Newark is more convenient if you’re staying in Jersey, JFK is close to Brooklyn and South Queens, and LaGuardia is close to North Queens.

On our 2026 trip, we splurged on a hotel right in Midtown Manhattan and I think it was worth it.

While much more expensive than staying in Queens, it allowed us to make the most of our time in the city. We could easily walk or take a short subway ride to everything we wanted to see and do.

We stayed at Home 2 Suites by Hilton Times Square and I would highly recommend it. The rooms were spacious (for New York) with pull-out couches and kitchenettes. Breakfast was also included!

4. NYC Win: Starting each day with a bodega breakfast sandwich

Nothing feels more authentically New York than starting each day with a breakfast sandwich and coffee from your local bodega. Not only was this a fun way to start each day, it was also delicious and budget-friendly!

We tried a couple of different bodegas that were between our hotel and whichever subway line we were headed to that day. Each morning breakfast was quick, tasty and we never spent more than $10 for two sandwiches and drinks.

5. NYC Win: Going to smaller museums

While New York City is home to some pretty huge and iconic museums, like the Met, the Natural History Museum and MoMA, it’s also home to a number of smaller museums that are just as awesome. We visited two on this trip that were excellent and I highly recommend them.

The first was the 9/11 Tribute Museum. While this museum doesn’t have all of the artifacts that the larger 9/11 Memorial & Museum has, it does offer a really special experience.

We went on a walking tour around Ground Zero and got to hear from a survivor who was working in the South Tower. Back at the museum, we heard from a man who was a survivor, a first responder and lost a loved one.

The entire experience was very emotional and all the more powerful because we got to hear from real people in a small setting. Sadly, the museum closed in late 2022 and is now an online-only experience.

The next small museum we went to was the Tenement Museum. At this museum visitors tour tenement buildings in small groups, learning about the history of immigrants and migrants to New York who were real residents of the building.

It was so cool to learn about the history of local people and walk through their actual homes. Instead of most museums where you broadly learn about huge movements of people, the Tenement Museum allows you to go deep into the personal story of one family.

6. NYC Win: Visiting The High Line on a weekday morning

The High Line is a public park and non-profit built on an elevated rail line on the west side of Manhattan. If you haven’t been, imagine a boardwalk suspended through the air, weaving through buildings, lined by beautifully manicured gardens, art installations and more.

We missed out on The High Line on our first visit to New York so we were determined to make it this time. We visited on a Tuesday morning before our flight home and it was the perfect time.

The park wasn’t too busy and we could easily stroll from one end to the other. It was very cool to walk along this urban park and get another great view of New York City.

By going in the morning and on a weekday, we were able to enjoy the park with only a few other small groups of people. In fact, when I shared a photo I took from our morning on The High Line on Twitter, a local New Yorker remarked that she had never seen it without crowds!

7. NYC Win: Eating some really great food!

While we did waste a few meals in New York, we also had some absolutely incredible ones. Here were my favourite places we ate at in New York City:

• Empanada Mama: Incredibly delicious empanadas for only $4.50 each? Yes, please! The seafood and shredded chicken flavours were my favourite.
• Junior’s: They say they have the most fabulous cheesecake and they just might be right!
• Nom Wah Tea Parlor: The oldest dim sum restaurant in the United States (or at least, New York) served up some pretty tasty dishes. Don’t miss the rice rolls!
• Motorino: It might be sacrilege to eat Italian pizza in New York but it sure was delicious!
• Vanessa’s Dumplings: The perfect little snack for a picnic in Central Park!
• Liberty Bagels: You can’t come to New York and not get a bagel! The ones at Liberty were tasty with lots of flavours, cream cheeses and topics to choose from.

And from our 2026 trip I’ll add Valla Table for Thai food, SIMO Pizza and the popular banana pudding from Magnolia Bakery and cookies from Schmackary’s, because they live up to the hype!

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Okay, make me feel better: Am I the only one who made mistakes on a trip to New York City? Learn from my mistakes and plan your own awesome trip with my list of 21 things to do on your first NYC trip and how to stay connected in New York!

PS: If you enjoyed this style of post, you can also check out the mistakes I made in Vienna.

 

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