Why You Should Get Lost in a New City

Before I head to a new city, I love doing research. I think many people would agree that it might even be the best part of your vacation. The food, the sights, the history, all feeding the insatiable wanderlust within you. This anticipation and excitement all wrapped into the weeks leading up to your trip can be exhilarating. Though a majority of this site is designed to help you plan your trip, we also think you should budget some time to get lost and appreciate the moment.

Why Would I Ever Want to Get Lost?

I know what you’re thinking, “isn’t this a travel blog?”. Well, yeah. And though it might sound a little ironic for this blog to start talking about the inundation of “best of” lists that flood the internet nowadays, the fact is it’s true. In the age of optimization and life hacks, we are continually looking to optimize for the “best” experience possible, whether that’s eating/drinking at the right spots or seeing what you’re supposed to see in each city. Personally, I know I’ve fallen into the trap of front loading too much research of my destination and trying to make sure I hit the “right” places for my Instagram fodder. In doing so, you end up rushing from place to place without taking the time to appreciate the city for what it has to offer. Another truth is that those “best of” lists are not exhaustive. They are a collection of places that bloggers (ahem, yours truly) thought were worth a look, but those lists are far from perfect for everyone.

The Basic Tenants

The fact that getting lost could be an “art” may be a strange concept. But there are a few tenants that will make your experience more meaningful:

• Leave the smartphone behind. It’s becoming cliché at this point, but we rely on our smartphones way too much these days. Whether it is looking up things to do or talking to distant friends, they’ve become a crutch and prevent us from existing in the moment.
• Get a physical map. We think Google Maps is fantastic, I mean our Maps section is built on them. But using a physical map can be just as easy and even stretch your brain a bit.
• Talk to random people. For some, including myself, this can be the most challenging. But it’s also the most impactful. I can’t tell you how many recommendations I’ve gotten from talking to random strangers while on the road. Some of the gems in this blog are from conversations I’ve had with people at a coffee shop, liquor store, bar. You name it.
• Bring a pen and notepad. Since you won’t have a smartphone to jot things down, do it the old-fashioned way!

Don’t Forget to Plan Ahead

Just because you’re going to wander in a city doesn’t mean that your pre-trip preparation can’t come in handy. When looking through those “best of” lists (insert plug for my City Guides), you’ll find patterns of which neighborhoods are worth visiting based on your interests. All you need to do is plop yourself in those neighborhoods and let your feet do the work. Figure out which sights you want to check out, write down the streets, and use your physical map to navigate.

Now What?

You’re ready to book your trip to hit the streets! At this point, all you need to do is pick a direction and see where your feet take you. Listen to the sounds of a strange and foreign city. Go to a coffee shop. Talk to the barista and see if they have any recommendations for the area. Go outside of your comfort zone. Get lost. The goal is to invite a little randomness into your trip.

Final Thoughts

In the age of social media, we are too obsessed with making sure our trip checks all the boxes that other people think it should. In reality, the only thing that matters is the experiences you have and the people you’re with. Years later, you’ll remember the little art exhibit or hole-in-the-wall burrito place you stumbled on. You’ll remember struggling your way through the confusing public transportation system. You’ll remember that fleeting conversation you had with a person you just met. You’ll remember getting caught in the rain completely unprepared. In the end, it won’t matter if what you did was on some list or not. What will matter is how those experiences, even if seemingly insignificant, changed how you view the world.