Why every twenty-something should travel to a new city alone

This month, I took a big venture and accepted the opportunity of a lifetime. With just three weeks to plan, I decided to travel solo to NEW YORK CITY for an affordable, future-related offer I could not resist (more details on that, in an upcoming post). I’ll admit, in the busy weeks leading up to the trip, I was entirely stressed and freaked out. I booked my flights from LA at 1am, anxious. I’d always wanted to visit the Big Apple, but I knew this surprise business trip would be the deciding factor if I could see myself actually living in the city sometime in my 20’s or not. Obvs I had to make it big, and attempt to do/see as much as possible in the single week I’d be there.

Camera: Fujifilm X30, a gift from my sweet Ian

I got disastrously sick in the days leading up to my departure, and life. kept. happening. By the time I arrived in Manhattan at the end of March, I was exhausted and without a plan. I found myself at the nearest Starbucks by the place I was staying, luggage in hand, trying to understand NYC’s web of subways and figure out what to do on the precious few days I had off.

Sandra, my super rad girlfriend from college whom I stayed with in the evenings, gave me some travel tips to work around my busy schedule, and explained the basics of transportation. Suddenly, I had the whole city at my feet (literally).

The thing with traveling alone is, you have to be open to everything. Every experience, every darkened subway stop, every random eatery or bar in weird neighborhoods… I’m not saying to try everything, because I certainly didn’t. But be open to the spontaneity of it all. No one is guiding you but your own two feet (and perhaps the Internet; ALWAYS have access to the Internet). Be okay with being alone. It might feel lonely at first (and you get a lot of weird looks, wandering around by yourself), but there is something undeniably wonderful about the independence, especially when you’re as sheltered as I am. So, with my feet flying and Google Maps to guide me, I took a leap of faith.

After a week, here are few places I stumbled upon:

Taylor Swift?
Taylor Swift in the subway?
Big Apple, little girl.
Big Apple, little girl.
Absolutely thrilled with Grand Central Station.
Absolutely thrilled with Grand Central Station.
Washington Square Park aka. NYU aka. DREAM SCHOOL
Washington Square Park aka. NYU aka. DREAM SCHOOL

(Proof that I wasn’t entirely alone in NYC – ladies of the Executive Leadership Program, class of 2016!)
Saw the iconic Broadway musical Les Miserables alone--and bawled my eyes out--for $45!
Saw the iconic Broadway musical Les Miserables alone–and bawled my eyes out–for $45! (Thanks TodayTix!)
concrete jungle
Concrete jungle.
Top of the Rockefeller
Top of the Rockefeller Center
King Kong.
The High Line in Chelsea (second favorite!)


Beautiful rainy day in empty Central Park
A beautiful rainy Monday spent wandering empty Central Park
Allyson wonderland
(Fact: will sell both upper limbs to get into this show.)
Inside the special collections of the New York Public Library.


St. Patrick’s Cathedral, after Sunday Mass
It’s amazing when you can step into a church, any church in the world, and feel instantly at home. Definitely my favorite place in NYC.
Iconic. (Taken from Staten Island Ferry)
Also iconic. Check out the OG cart on 53rd and 6th St!
Bouquet of Sunflowers, by Claude Monet, on display at the Metropolitan Museum of Art.
Museums are PERFECT for a rainy day.
Not-so-wooly MAMMOTHS! at the Museum of Natural History
Not-so-wooly MAMMOTHS! at the Museum of Natural History.
Mornings spent listening to my favorite busker, in front of the John Lennon “Imagine” memorial in Strawberry Fields, Central Park.
Cheesin' on top of Belvedere Castle, Central Park.
Cheesin’ on top of Belvedere Castle.

(And those were just the highlights.)

Most of these stops were spontaneous, squeezed in between classes and networking events, with just two and a half days I had completely free before my afternoon flight home. Without an official itinerary or agenda, I was able to experience at least four main parks, four fancy restaurants, three trendy bars in trendy neighborhoods, three islands (Ellis and Liberty, and yes, Manhattan is an island), two schools (CUNY and NYU), two museums, two churches, two Broadway shows, and one gorgeous NYC view (on top of the Rockefeller Center! Go early in the morning when it’s practically empty). And I somehow accomplished all of this in a week.

(Do I know yet if I’m going to live there? We shall see 😉

If you’re not yet convinced, there are many benefits and reasons to exploring solo, including:


Even if you have a busy schedule or places you want to see, being solo means being flexible. You’re able to make your own decisions, wander onwards, and literally stumble upon places without relying on others’ decisions/opinions or having to change course. For my two totally free days, I made it a point to visit at least TWO big sights on my list, and explored between stops (plus navigating the subway, or randomly going somewhere nearby) that were close in distance. I didn’t have to worry about being late somewhere or anyone else’s agenda; I was able to take my time and fully be immersed.

You meet people.

Especially when traveling in big cities, you either purposely stand out, or fit in. You get to meet the most interesting people in your solo travels; people who will genuinely help you, families with their parade of kids, millennials also traveling solo and living in the moment. And in a place like the Big Apple, it’s easy to get lost and caught up in the rush, but as long as you can read basic signs and are street-smart, communicating isn’t bad. Taxi/Uber drivers were not big jerks like everyone thinks, and the locals (building doormen, city students, longtime New Yorkers) are generally willing to point you in the right direction. Ask nicely, be friendly, and they won’t judge you. Just don’t ask them to take your pictures–the other billions of tourists around will do that! (Pro-photo tip: Always ask the guy with the HUGE DSLR CAMERA around his neck.)


I sort of touched upon this earlier with flexibility, but being on your own also requires you to think, act, and make quick decisions on your own. When suddenly thrown into the deep end, you’ve got no other choice but to swallow your fears and figure it all out. (Pro-NYC subway tip: Know your stop before you board, especially the difference between “uptown” and “downtown.”) I struggle with this a lot in my own life and at home, but when traveling solo I felt my instincts kick in, and I’ve had plenty of city commuter experience before. Survival mode can take you to the craziest (and most wonderful) of places: be prepared for pleasant surprises along the way.

Finding yourself.

They say travel is about “getting lost and finding yourself.” The truth is, finding yourself is an ongoing journey. It takes trial and error, rejection, and plenty of mistakes that will occur along the way–but it also takes courage, strength, and willingness to persevere. It takes work and being open: openness to experiences good and bad, and to getting “lost” on occasion. But above all things, it takes courage. You don’t have to be the strongest, most expert person to travel alone, and you don’t have to know everybody along the way. (Sure it helps, but so does simply talking to people! Like I said, the right people will help you.) Stepping out of your comfort zone and into the unknown is scary, and it might feel a little like drowning. But with faith, the right mindset, network of support, and a map or general plan to guide you, you can get lost anywhere and find yourself along the way. It’s all about taking that first step.

To a lifetime of endeavors and adventures,

Screen Shot 2015-09-12 at 1.27.39 PM

(PS: For similar travel reads like this, check out my friend Agnes’ post on Backyard Destinations! She also saw a Broadway show alone and lived to tell the tale)

One thought on “Why every twenty-something should travel to a new city alone

  1. ❤️❤️❤️❤️. Every detail and experience of your journey has been nothing but wonderful. It felt like I was actually there doing the things, exploring the different places you went to. Thankful to God for another blessing! Love you Ally! May God continue to reward you with more blessings and take you to places and new adventures

Leave a Reply