April 21, 2021

9 tips & tricks for exploring a new place.

9 tips & tricks for exploring a new place.

As you’ve heard me mention on the podcast several times, I absolutely adore exploring. Few things make me feel more alive than strapping on a pair of sneakers and going somewhere I’ve never been. 

Nearly every free weekend in the past four years, I’ve ventured away from home. On any given Saturday, I’ll visit a new city, small town, mountain, bike trail, park, restaurant, museum, mall, etc. 

Whichever vibe I’m feeling on a given day.

This curiosity harkens to my childhood. As a kid, my family and I vacationed in Hyannis, Massachusetts, for 11 years in a row. We stayed in the same hotel every summer, eating at the same restaurants and playing the same miniature golf courses. In the moment, I enjoyed the familiarity, the routine. 

A mysterious dome structure sat at the top of the hotel. When I first saw it, I imagined climbing all the way to the top. From there, I thought I might be able to see the ocean. Or another continent. Maybe my favorite planet, Jupiter.

I climbed every staircase in the hotel. I walked up and down the vacant hallways, peering inside the custodial closets and entering rooms purposefully marked as “temporarily closed.” Something, anything, just to find the doorway to the dome.

I repeated this process for the next 10 years, hoping some new piece of information might surface, that the secret passage would reveal itself as I grew older. I even began bringing my dad with me, hoping his wisdom could help me uncover details I’d possibly overlooked.

I never succeeded.

Fourteen years after that first Cape Cod vacation, I studied abroad in Scotland. A far cry from the seagull-filled beaches of Hyannis and Barnstable, I fell in love with the bonnie lochs, hills and Scottish coos.

My entire worldview opened up. I realized how little I’d seen up to that point, and how much learning I could do about myself and the world if I just rekindled the same curiosity that swept over me as a child in Cape Cod. Failed journeys to the hotel dome morphed into successful journeys to the summit of Ben Nevis and Brunelleschi’s dome in Florence. 

From that point on, I committed to leading a life of adventure. 

The good news? I don’t have to book flights and hotels to do all of this. Sometimes, I can learn new things by driving 20 minutes away. Adventure is everywhere; we just have to find it.

With all of that said, I want to share some of my methods for exploring, things I make sure to do every time I head out on a day trip to a new city, such as Denver, or a small town, like Manchester, Connecticut. 

Remember: This is MY approach, so it might not work for everyone. But it’s my hope you can extract a few key points so that you can get the most out of the next time you take a day of exploration, whether it’s with friends or by yourself.

But first, what should you bring? You’re a millennial/Gen Z’er, so of course you’re rocking a backpack. You’ll want to pack lightly since you’ll be on foot all day.

  • Journal
  • Book for reading
  • Pen
  • Sunscreen (if the weather calls for it)
  • Raincoat (any time the forecast calls for below 70 degrees, I bring my coat just in case. If I don’t wear it, I loop it through my backpack or tie it around my waist)
  • Mouthwash (I drink lots of coffee on my adventures, and no one wants afternoon coffee breath)
  • Protein bars (I hope to not eat them, but I always prepare for the possibility that I’ll end up desperately lost)
  • Water bottle(s)
  • Phone charger
  • Headphones (It can get scary walking alone at night, so I like to listen to music or a podcast to drown out the occasional eerie silence)

Now you’re ready to explore.

1. Do your presearch (yes, I made up this word)

Traveling is all about finding the right balance between having an itinerary and not having an itinerary. You don’t want to completely pack your schedule because if so, you’ll leave no time for exploring that curious cobblestone street or stopping to watch that street performer. 

On the other hand, if you head in with no plans, you risk aimlessly wandering and not getting the most out of your experience.

Beforehand, I usually identify a couple of coffee shops, breweries, restaurants, botanical gardens, museums and/or parks that I wouldn’t mind seeing. I usually walk to these places, but along the way, I leave myself open for window shopping (especially bookstores) and checking out anything that sticks out to me.

You’ll also want to research the area beforehand because you’ll want to have a greater appreciation for the place in the moment. If there’s a famous monument in the city, you’ll want to know about it so that when you come across it, you’ll have a little background info on it. You can point to it and say, “Wow! That statue came up in my TripAdvisor search!”, rather than look at it and not know why it’s significant.

2. Wear the proper footwear

If you’re exploring the way I do, you’ll spend your entire day on foot. I usually log between 25,000 and 35,000 steps on a solo exploration day, so you need to make sure you’re prepared with the right footwear. Wear comfortable running sneakers and a pair of athletic socks to help you power through the day’s adventures.

3. Make time for reading and writing

If you know me, you know I don’t care much for other people’s opinions of me. I do what I want, when I want. But I’m beginning to realize that some people may view some of the things I do as … odd.

At a coffee shop, after some good people-watching from the seat next to the window, I love to break out my journal. Or my book. That’s fairly normal.

But … I also bring those books to the bar.

Why? Few things relax me more than an IPA and a good book. Since these solo travel days are my designated times for slowing down, I really take the time here to examine my life and what’s going right and wrong, and the things I can do better. Plus, when your mind is slightly altered, you begin to view things in a different light.

I don’t care if you think it’s weird.

4. Fill your water bottle at any moment you can

You’ll burn thousands of calories on foot all day, so it’s critically important to stay hydrated.

Before leaving any coffee shop, restaurant or bar, I ask the wonderful employees there if they could fill my bottle with tap water. Or I ask for a pitcher of water at my table, and then I fill my bottle with the remaining water.

If you ever stumble across those filtered water fountains on your journeys, you need to take the opportunity to fill up with that water. It’s immaculate; not quite on Fiji level, though (link).

5. Go to the bathroom at any moment you can

I learned this lesson the hard way in Milan when I had to PAY to use the bathroom at the train station. Since then, I take any opportunity I can to use the restroom, even if I don’t need to.

When I explore, I consume a lot of coffee and water, practices that require regular maintenance. If that means entering a public place where I don’t intend to buy anything, then so be it. I’ll go into a shop, use the bathroom and then browse afterward to give the impression I came in to purchase an item.

6. Charge your phone at any moment you can

Obviously, none of us can rely on our intelligence or intuition to get us places. So we let our smartphones navigate us when we need to get somewhere. The Maps app can eat battery life, so any time I’m seated inside, I try to sit near an outlet so I can plug in and charge. I live in constant fear that I’ll never make it back home, so I want to extend battery life for as long as I can.

7. People watch

If you don’t have to be anywhere at a specific time, I encourage you to stop and rest every once in a while. Find a park bench, take a seat and observe your surroundings. Watch other people. You can learn a lot about the world by temporarily removing yourself and focusing on the actions of others.

Last year, when I was in Copenhagen, I sat on a bench at a public ice rink. I watched couples young and old holding hands, keeping each other upright on the ice. I distinctly recall a young couple that fascinated me. So I took out my notebook and wrote a short story about them, conjuring all the details about how they had met and fallen in love.

Try something like that. It’s really fun writing other people’s stories.

8. Keep your wallet/phone/keys in front pockets

Ah yes, the famous wallet/phone/keys pat-down we all do before entering and exiting public places (this process now includes the mask as well). 

Unfortunately, mean people exist in the world. Depending on where you are, sometimes the streets are lined with nefarious folks just waiting to steal from an innocent young person walking around.

I always put my valuables in the front pockets of my jeans. That way, if someone attempts to pickpocket me, I’ll notice because it means they’re reaching for … you know. 

For further protection, I also tend to walk with my hands in my front pockets so that I can keep my paws on my phone, keys and wallet at all times. Obviously without any of those, we’re screwed.

9. Eat lightly

Since our time in these places is limited, we of course want to sample as many different local flavors as we can. So it’s key to eat fairly lightly throughout the day. Plus, because of all the walking, we’re guaranteed a consistent appetite.

I always begin the day with a big breakfast at home. I need the fuel for my adventures.

But a few hours after that, once I’ve arrived at my desired city/town, I like to nibble throughout the day. A sandwich at this place. A pastry at that place. Something small at a street cart. Perhaps an appetizer (pita chips and hummus, anyone?) in the late afternoon and then dinner not too long after that. It’s not uncommon for me to eat at maybe four or five different establishments in a given day, whether by sit-down or takeaway.

Voila! Those are my nine tips and tricks for successfully exploring a new place in your free time. If you’ve found this helpful, please contact us and let us know! We’d love to hear about your explorations.

Happy adventuring!