What’s the best way to explore a new city?
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Apparently, we’re back to the travelog.
I suppose the responsible answer is that you should research the city ahead of time, make a list of the important landmarks, buy tickets in advance, map out your route and carefully schedule every hour so you don’t waste a minute.
That sounds exhausting.
When I visit a new city, I certainly want to see some of the things I’m supposed to see. If I’m somewhere with a famous landmark, I’m probably going to go look at it. There’s a reason people visit those places. But I don’t think you really discover a city by spending the entire trip moving from one item on somebody else’s Top 10 list to another.
The best way I’ve found to explore a place is to give yourself enough of a plan that you don’t spend half the day wondering what to do, but leave enough holes in that plan to wander a little. Walk when you can. Drive through neighborhoods that aren’t part of the tourist district. Find a local restaurant instead of eating somewhere you could have eaten back home. If you see an interesting store, bar, museum, church, historic marker or giant roadside chicken, stop and investigate.
The giant roadside chicken may end up being the highlight of the trip.
And talk to people. Bartenders, servers, shop owners and people sitting next to you often know far more about what you should see than whatever list popped up first on Google. Ask them where they eat. Ask them what part of town visitors overlook. Ask them what they’d show somebody who had never been there before.
Some of my favorite travel memories haven’t come from the thing we planned months ahead of time. They’ve come from the place we stumbled across because we took a wrong turn, changed our minds or decided we weren’t quite ready to go back to the hotel.
So I guess my answer is: have a plan, but don’t become a prisoner to it.
See the landmarks. Eat the food. Walk around. Talk to people. Take the wrong turn every now and then.
And if there’s a bourbon distillery nearby, I consider that an important cultural and historical site.
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Copyright © 2026 Doug DeBolt.
