Goodbye to the Decade – My 2014 Birthday Trip to New York City and Why I Like Traveling with My Friends

This post is part 5 of my 10 week retrospective looking back at a specific trip from each year of the 2010s. Read more about the series here. Today I’m talking about the 2014 collective birthday trip my friends did in New York City. Previous editions of this series include


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, and myself and another friend were still 29, but April worked best for everyone.

Washington Square Arch in Washington Square Park in New York City.

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 of. 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).

Bright lights and billboards of Times Square in New York City at night.

One of the things my friends and I did on our trip was 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 we never felt any pressure 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 chill at the hotel). My two friends who hadn’t been to New York City went up to the Empire State Building, but my friend and I who had been to New York (and did the Empire State Building on previous trips) 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 to, but no one was dragged along to anything. I never felt like I had to do something or another. And in the back of my mind I knew two things

1. You can never see and do everything in New York City and

2. You can always come back. Things might be different, but you can come back.

View of the Upper East Side of Manhattan and the East River from the Roosevelt Tram

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 (worst thing was my shoes were crap and hurt my feet, and it rained really hard one night and my umbrella broke). And 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. I am someone who likes to have hope and so 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. And 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. 

Check Out More Posts About New York City on Take on the World

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