Goodbye 2010s | My 2014 NYC Birthday Trip and Why I Like Traveling with Friends -

Update for 2025. This post references visiting somewhere in the United States. While I’ve had great visits to the U.S. in the past I don’t recommend travelling there at this time. This post is my current stance on U.S. travel. Information regarding prices, operating hours, or other details in may have changed since the original publication.

This post is part of my 10-week retrospective looking back at a specific trip from each year of the 2010s. Read more about the series here. Below are links to every post in this series.

In 2014 three friends and I decided to go to New York City to celebrate our collective 30th birthdays. We went in April. Two of my friends had already turned 30 as of that trip, (myself and another friend were still 29), but April worked best for everyone.

Washington Square Arch in Washington Square Park in New York City. We knew the weather in April might be a bit rainy, but it was generally pretty nice for our trip (minus one torrential downpour that ruined several umbrellas).

This was my third trip to New York City, one of my friends had also been before. It was the first time in New York City for the other two. We decided to go to New York City because we knew there would be lots to do. We all love theatre and musicals, and there are so many sites to see. New York City is a place I could visit again and again and not get bored. I’ve written about the interactive experience of Sleep No More that I did during that trip (one of the coolest theatre experiences I’ve had) and seeing the musical If/Then (now closed, such is the life of most Broadway musicals). We went on a Food Walking Tour and a Broadway Walking Tour. We did some touristy things like eat at Ellen’s Stardust Diner and we went on the Ferris wheel at Toys R Us in Times Square (while it was still there).

One of the things my friends and I did on our trip was to visit Times Square. I’d been before, but I actually enjoy going there and wandering around. I’m sure if I lived in New York City the novelty would wear off pretty quickly.

One of the great things about that trip was that we didn’t feel pressured to do everything together. My friends went on the Staten Island Ferry (to get photos of the Statue of Liberty), but I skipped out because I’d done it before (and more pressingly my feet were killing me and I just wanted to relax at the hotel). My two friends who hadn’t been to New York City before went up to the Empire State Building. My friend and I who had been to the Empire State Building on previous trips went and had dinner and drinks instead. One afternoon I took off on my own and wandered around Brooklyn. Don’t get me wrong we did lots of stuff together, but no one was dragged along to anything. I never felt like I had to do something or another. In the back of my mind, I knew two things.

You can never see and do everything in New York City and
You can always come back. Things might be different, but you can come back.

One of my friends and I decided to take the tram to Roosevelt Island. This is the view of the Upper East Side of Manhattan and the East River on the way back. Then we got a cupcake from an ATM, because what else are ATMs for? Money? Pshaw, I say.

My 2014 Birthday Trip to New York City was a pretty stress-free event. The worst thing about the trip was that my shoes were crap and hurt my feet, and it rained really hard one night and my umbrella broke. Perhaps my attitude was a bit lackadaisical because I had been to New York City twice before. I didn’t have this pressure of thinking, “Aaah I have to see and do everything!!” I believe that’s a problem a lot of people can get into when they first travel. You want to see and do it all, but you have to make peace with the fact that you just can’t. As someone who likes to have hope I don’t ever tell myself “this is the only time I can ever visit this place” because that just leads to more anxiety. And there are many places I’ve visited several times. I have no doubt in my mind that I’ll end up back in New York City at some point again in the future. Whether I go back to some of the same places or see something new I’ll have an enjoyable time, but it won’t be quite the same as that 30th birthday trip with my friends.

Have you taken a trip with your friends?