Travel: How to Decide What Cities to Visit

The eagle is landing
The eagle is landing

We’re going to the US for a month in April!

Amidst our slow preparation for the trip—finding friends to take care of our Airbnb apartment, to look after and love Brownie while we’re away—we’ve been asking each other where we’d go.

And we never came to any conclusion. We don’t know which cities to visit.

The US is huge, especially for someone from Singapore, and it’s impractical to stopover at more than 6 cities in a month (5 days per city). That’s pretty much what we know.

Aside from the occasional American drama series that we binge watch together (Friends, The Mentalist, Suits, Big Bang Theory), and the famous cities like San Francisco and Los Angeles that we’ve been before, we really don’t know much about American cities and the people who live in them.

So we’re in a rut, albeit a good kind: we have a potentially awesome trip planned, but if we don’t know much about the cities we’d like to visit, it wouldn’t mean much to visit them at all!

Being the millennials that we are, we Googled. Various search terms…

  • articles to read before going to united states
  • how to choose/decide on cities to visit in united states
  • how to prepare for a roadtrip to the united states

The results we got were a combination of the following, which are not useful to us one month before a big trip:

  • Literary works, like de Tocqueville’ Democracy in America
  • Travelogues, like Heat-Moon’s Blue Highways and Steinbeck’s Travels with Charley
  • Fact list-icles, like “18 Things Everyone Should Know Before Visiting The USA”
  • Categorical list-icles, like “10 Best US Cities to Visit on a Budget”
  • Other list-icles, like “20 Best Cities for 20-Somethings”, and preposterously widely casted list-icles like “10 Best Cities to Visit in the United States!” (with the exclamation mark)

Can’t recommend any of these as articles to base a true travel trip on.

If you have at least 2 months before a trip, however, I’d recommend Lonely Planet’s comprehensive list of “travel books to read before you go”, which covers practically any country anyone cares to visit. Reading books like travelogues or travel fiction is admittedly still the best way to dig deep into the idiosyncracies of a place and its people.

Truth be told, my gripe here is a little luxurious, but not one that’s unwarranted. Remember a time when travelling overseas was a big (big) deal? That was before online ticket bookings and budget airlines.

My wife and I—and I imagine, you—live in a world where it’s possible to be in New York one night for a meeting, and be Sydney the very next for a friend’s wedding – all without having to rob a bank.

What that means is that there hasn’t been a whole lot of build-up prior to us buying those tickets. We’ve always had the confidence that we’d one day go to the US and do an across-America trip, so we didn’t think much before today.

And because of this confidence and how accessible flights are to middle-income people like us, we book flights to places more sporadically, sometimes on an impulse. And why not? It certainly adds to its memorableness. (I remember fondly a trip to London and Paris with a friend in 2011 where we booked our flights in university campus without thinking twice, after realising the prices were really low and that we’d be on winter break. It is particularly unforgettable because of how we decided to travel on a whim.)

The problem with booking trips one or two months before the adventure is that there’s very little time to read up appropriately to decide where to visit. That is, after all, not a decision to made arbitrarily since… well, since the world is so freaking big.

So What Now?

I’ve started doing some research, which will probably involve a lot of reading to determine which cities fit our broadly-defined aims for the trip, which are really quite simple:

  • To observe people in different cities and see how different people can be in their unique environments
  • Learn history by seeing monuments and reenacting (in our heads) what happened in the past at which places
  • For the cheap-thrill in us, to see places often portrayed in TV shows that we spend a lot of time watching

Your aims will likely differ from ours, but probably not drastically. Unless you’re on a pilgrimage with a specific objective, the overarching reasons you like travelling are probably generic:

  • See the different parts of America with your own eyes
  • Observe the life of Americans in their homeground
  • Synchronise impressions of America with reality

I’d add one last point, which is to “see if we like a particular city”, because the truth is, it’s now easy (and exciting) to move abroad and start a new chapter of life. Well, easier than ever before, that is. And it could be for just a couple of years.

Wanderlost
Wanderlost

Cities to Visit (Not Go Blind)

I’d hate to go to the US—in fact, any foreign country—without first knowing more than a little about its history and culture. To me that’s like travelling as a blind person: I won’t know what I’m (not) seeing. A trip like that offers only a vague sense of the places we visit, which is not much at all.

So I’ll be posting updates on my blog on the research I’d have done. My approach is to use Wikipedia as the springboard to dive into specific cities and learn more about them along the way, which probably involves reading blogs, old and new news, as well as short travelogues.

We’re stoked that we’re going to (/across) America. But now’s the time to sink some teeth into articles that explain just what the US has been and currently is, and prepare for a(nother) trip of a lifetime. Do it now or risk going blind.

Photos by various photographers under CC Zero license found on Unsplash.