On exploring a city. Well, I am not necessarily against traveling with the Lonely Planet in your hands, against spending weeks preparing your city trip, against visiting each and every one of the top-10 things you found in that influencer blog post. I just think there are more fun ways to travel. When you’re not overly prepared, when you have an open mind, you’re more open to new impressions, to making new memories. When you let your high expectations go, everything that happens is better than expected. It’s the reason I often travel on my own, why I often let the chef choose my food and why I started this blog. But when talking about it, whether it is on a conference or with friends, people often ask – so how to explore a city?

Several tactics I use when exploring a city:

  1. Ask a local
  2. Ask someone cooler than you
  3. The chain of asking
  4. Don’t ask, just follow
  5. Live like a local
  6. Go left when you need to turn right
  7. The street behind the street
  8. Use data

1) Ask a local to explore a city

This is the easiest. Whether it is the best place to go, the best place to eat or even what to eat, just ask a local. Pretty much any local. Whether it is a local friend, a local friend of a friend, your Airbnb host or someone on the street. Rather than asking them for tips (which would normally make them inclined to come up with tips for tourists), ask for their favorite places or the places where they are/would be going that day.  Sometimes the conversation will actually end up in them inviting you over or joining you for parts of the day.

Amazing Tokyo food experience with the legend Chieko Ogawa
Amazing Tokyo food experience with the legend Chieko Ogawa

I had such an experience when I asked a friend of my mother’s for some tips in Tokyo. We ended up in a super small 9-person restaurant that would only serve eel and different eel preparation. After that, we ended up in an amazing sake place that was situated in a non-distinct tower near one of the big Tokyo stations. It was amazing.

Omakase in Kanteki in Tanabe in Japan
Omakase in Kanteki in Tanabe in Japan

And most notably, I had my first true Japanese omakase (お任せ) this way. When visiting a small coastal town (Tanabe) just before hiking the Kumano Kodo, I ended up in a small restaurant that was super hard to find. Because I did not speak Japanese and the owners clearly didn’t speak English, I turned to omakase. It pretty much means, “I’ll leave it up to you”, inviting the chef to be innovative and surprising in the selection of dishes.

2) Ask someone cooler than you to explore a city

This is closely related to point 1, ask a local, but might give some more specifics to asking locals. Spotted a really cool clothing store? A super hipster barista? That cool dude in the co-working space? Ask the person cooler than you for some tips.

The manager of the breakfast place we visited during our recent Madrid trip, was clearly cooler than me. In all ways possible. Not that it’s super difficult to be cooler than me (most people are), but he clearly was. So we asked him what would be his favorite places to get dinner. Although his tips were mainly skewed towards more touristic places, he advised us to go to Fismuler, which turned our to be an amazing place for dinner.

3) The chain of asking to explore a city

I usually start by asking one local for some tips, then go to that place/these places and repeat the same question. This creates a chain of asking, a chain of tips so you will that will lead you from that one nice restaurant to a great bar after to some ideas to visit the city the next day to some amazing lunch place to … well, you get the idea.

4) Don’t ask, just follow to explore a city

When I was visiting Kyoto a few years ago, I almost bumped into a bunch of people queueing up in the middle of the street. I had no clue what it was, so guessed I would just queue up. Locals usually know what’s good, so if you find something a local deems worth queueing for, it might very well be worth queueing for.

Queueing up on the street in Kyoto
Queueing up on the street in Kyoto

That place where is everyone is queueing for coffee.
The place where everybody runs to during lunch time.
The place where everybody is queueing up for pizza (we had some amazing lunch pizza in Naples this way).

Ah and yes, it might very well not be worth queueing for, but at least then you’ll have an amazing story on how you waited 30 minutes just to have some free horrible soup or entrance to a crapy bar.

5) Live like a local to explore a city

This is pretty much the hardcore version of ‘don’t ask, just follow’. Try to truly adapt to the pace of a city and its inhabitants by following their daily rhytm. Explore a city or a part of the city by doing what the locals do. Browse the street, have a coffee on the same corner where they’re having a coffee. Get a newspaper in the same store. Have lunch like them. Spend the afternoon playing checkers or petanque. Just eat, breathe, live like they do.

6) Go left when you need to turn right to explore a city

I actually used this to get to know both Amsterdam and Gent when I moved to the city. Often, you’ll have a rough idea of how to navigate through a city. What the shortest route is. And this is actually a great opportunity to exactly go the other way, to explore a street, alley or part of the city you wouldn’t normally cross.

So go left when you know the shortest route is right.

Take the detour.

Rooftop view in Gent
Rooftop view in Gent

7) The street behind the street to explore a cit

This is similar to going left when you have to turn right. Often the best places are ‘hidden’ in a street just next to the main shopping street. So take the time to explore these hidden streets and find the hidden gems.

8) Use data to explore a city

I wrote a separate blog post on how I find running routes in cities I don’t know. Much of it is merely based on smart use of data, in this case, Strava data. Using the most popular running segments in a city and a heat map of the city, I get quite a good idea where the popular (and presumably good) running routes are.

Same goes for using Foursquare/Swarm (popular check-ins or popular places overall) or even Google data (busy times of stores and restaurants).

So, that’s it. What are your tactics to explore a city?

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