Is there a strategy for knowing which countries and cities you’ll enjoy visiting?

Apart from these monkeys (at the botanical garden), all our Penang photos are of us pulling silly faces

We had a bit of a not-so-great experience this week.

It all started because we’re idiots and booked a 66-day trip on a 60-day Thai visa. Then, because we can’t just be like any normal people and get the bus to hop over the border and back, we decided to make a week of it.

We ended up (after a few days in Bangkok) in Georgetown in Penang, Malaysia – a place that Wikitravel states “does not offer that much to the adventurous tourist”. Great! We’re the last people to self-identify as “adventurous tourists”. It went on to talk about the beautiful old town and the unbeatable food, and we were sold.

Turned out that we and Penang didn’t get along. The food was fine (although massively overhyped), but the coffee – our main vice – sucked. The architecture was nice, but as it’s colonial British style we’re kinda used to it. Walking anywhere was terrifying, the people were moody, and coffee shops with wifi just weren’t happening.

We still had a good time, because we always do. But landing back in Chiang Mai and being “wai”‘d at by the girl in the 7-11 felt like coming home.

This is weird for us. This past year we’ve lived in a lot of different places, and we’ve always felt at home – so we assumed that as long as we had our laptops and each other, we’d be sorted.

Now that we’ve found somewhere we couldn’t imagine staying for more than a week, it’s clear we must’ve just got lucky so far.

So this raises a question: how do you work out in advance whether somewhere will be right for you? Is there a framework for making decisions about where to live? It doesn’t matter so much for us because we have plenty of time to try everywhere (especially if we keep cocking up our travel dates and need to make visa runs every five minutes), but what if you need to choose just one of several competing places to settle in for a year or more?

It’s clear you can’t rely too much on other people’s opinions, because everyone has their own priorities. But more troublingly, we’ve now realised it’s not always possible to know your own priorities.

For example, we thought we were so unadventurous we’d want to live somewhere where English was widely understood. But really, we get sniffy about hearing too much English around us and always seek out the most “local” spots where we can point and smile our way through. We also thought we’d only be happy in bustling, dynamic cities, but it turns out we loved laid-back places just as much.

After thinking about it a lot, we’ve isolated a few things that do seem to matter to us:

  • Interesting daily life to observe. We like walking around and being amused by an entire family – including pets – on a moped (Chiang Mai) and spontaneous sidewalk dance parties (New York).
  • Prettiness. Both architectural (Chiang Mai) and natural (Vancouver).
  • People who make us feel welcome. Hence loving Berlin, Vancouver, and…Paris (yep, the stereotype has gone wrong there).
  • Cafe culture. We like to sit and work, or read our books, or just chat. When we’ve got lots of options to do that (Boulder, Colorado, New York), we’re happy.

Now we think we’ve got a handle on what matters, we’re going to use these criteria when choosing where to go on our Eastern European trip this spring – so there’ll be less relying on the general impression we get on Wikitravel, and more reading between the lines to see whether it’ll tick our personal, slightly strange boxes.

But we’re still none the wiser about how you can know what matters to you in advance, and make more permanent choices with confidence (or even just decide where to go for your annual two weeks off). If you’ve got any tips that work for you, reply and let us know.

So screw you Penang and your massive holes in the pavement for no reason, yourcoffee shops that aren’t and your “eclectic” food which is all basically noodles in soup. But thank you for making us realise how lucky we’ve been.

  • Sally

    Sorry to hear you didn’t like Penang! I actually really enjoyed it. But this could be because I spent the two months prior to Penang living in a rice farm, wading through rice paddies. So maybe this is the key to liking a place? Spend two months wading through rice paddies before you go there & you’re bound to LOVE the place… just as long as there are no rice paddies there.

    • Rob @ Making It Anywhere

      That sounds like the basis of a good rule for life to me!

      On the basis that it’s all relative, maybe we should aim to spend half of our time in really shitty places and the other half in mediocre places. We’ll save a damn fortune, and be happier than if we try to maximise for awesomeness all the time.

      Then it’s just a case of getting the length of each cycle right. It’s like after you’ve been ill and you think “Wow, this is awesome – I’m never going to take my health for granted again!”…then 10 minutes later you’re losing your shit because Vimeo’s buffering slightly too slowly than you’d like. Habituation is a bitch.

      I’m possibly over-thinking this now.