Wandering Thoughts #1: Would You Travel Without an Itinerary?

our lives are unmapped journeys

A good traveler has no fixed plans, and is not intent on arriving.

—Lao Tzu 

Hi friends, and welcome to the first iteration of Wandering Thoughts, a monthly series for paid subscribers with inspiration for living an adventurous, net-positive life. These are mini-guides and musings for all you fellow seekers, wanderlust junkies, and soulful explorers who want to leave this world a little better—a place where we can discuss the ways our journeys help us grow. This inaugural edition is free to give you a taste of what’s to come, and the theme is what happens when we ditch our itineraries, maps, and digital devices.

Nick and I are going on a big road trip this fall. We’re starting in Bulgaria to attend a wedding and will meander the countryside before flying to Vienna and driving south through Slovenia and Croatia.

Neither of us has been to the Balkans before, and we’re so excited to explore the region (please drop any recommendations in the comments!). We don’t have much of a plan other than the main stops, and the feeling that we need a packed itinerary is gnawing at me. My usual method of trip-planning includes a fair amount of research, plotting out restaurants and coffee shops on Google Maps, and deciding more or less what we want to do each day of the trip…but something keeps stopping me. Maybe it’s the free-wheeling high of quitting my job, or maybe it’s that I don’t have many preconceived notions about the region and therefore don’t have things I’m dying to see and plan around, but I keep looking at the blank spaces of our itinerary asking to be filled in and thinking, what if I just…didn’t?

After all, the beauty of a roadtrip is the ability to travel on your own timeline and according to your whims. There are no planes to catch, no trains whose tracks keep you on a pre-ordained path. The thought is both freeing and terrifying. We could drift however we please, stopping and staying awhile whenever and wherever we find something that interests us; what we’d sacrifice in the comfort of having known plans, we might gain in discoveries we wouldn’t have otherwise made. On the other hand, not doing our research means we could miss incredible things that were right under our nose, or get hopelessly lost, or arrive somewhere and find there is no place to stay (a thought that scares the bejeezus out of me).

So friends, I’m wondering: have you ever traveled without a plan or without knowing exactly where you were going (or jumped blindly into some other unknown)? How was the experience for you? If you haven’t, would you try it?

I recently read this New York Times travelogue penned by a man who trekked through Switzerland without a phone or an itinerary. The author relied on the generosity of others to find his way, using hand-scrawled maps from locals and occasionally crashing in barns. I found it to be equal parts inspiring and comforting—I tend to forget that things can be done the old fashioned way, and this story is proof that we don’t actually need a detailed plan or digital aids to get by (in Switzerland and elsewhere; people are people no matter where you roam).

Of course, traveling without planning ahead or the comfort of Google maps means accepting a lot more uncertainty that we’re used to in today’s uber-connected world. But that uncertainty has its virtues. In this CN Traveler piece (which just so happens to be written by Caravanserai community member

Narina Exelby

of Travel: NE Where!), women tell stories of traveling solo before the era of iPhones and ubiquitous wifi. The lack of instant access to information forced them to be flexible, to trust their instincts, and to be present in the moment.

As Hilary Exelby tells Narina, “[t]here were no deadlines or expectations, and getting lost was never a problem—we’d just go a different way.”

In other words, these brave women just kept diving into the unknown over and over again, a concept that feels somewhat foreign to me. While travel is always a journey into the unknown to some degree, the computer in my pocket gives me at least some knowns—far more than past generations had—and that, to me, makes the world feel much less scary. There is good and bad in this. I love that the globe feels small and accessible, because I want to see as much of it as I can; on the other hand, I can’t remember the last time I truly felt challenged on the road, and part of me longs for those growth experiences that have become fewer and farther between in this world where we can arrange so much at the click of a button.

“When you’re not leaning on this device, you’re more vulnerable,” a traveler tells Hannah Docter-Loeb in Slate. “But in a certain way, that’s a good thing, because it does push you to ask people for help or directions. And built into that was this patience. You always kind of had to wait. That instant gratification, that instant need for an answer, wasn’t there. You knew things would take time.”

I think this waiting—this absence of a clear plan telling us what to do and where to go next—forces us to dig deep inside ourselves. What do I want to do right now, with no one else directing me? Can I figure this out on my own? These are useful questions not only in our travels, but in our lives writ large, because we never really know where we’re going, or how, or when; at best, we can see the few steps in front of us.

As for my own trip, I don’t plan on chucking my iPhone, but these stories have given me the urge to let the road unfold in front of me without expectations or too much research. I’m craving a solid balance between predictability and openness—enough planning to have a general idea of where we’re headed, with enough unscheduled time to allow for organic discovery and maybe getting a little lost.

And if that minimal itinerary doesn’t serve us, we’ll take a note from Hilary’s page and just go a different way.

good stuff from around the world (wide web)

Here are some reads that have captured my imagination lately.

1. Cup of Jo recently did mini interviews with seven women who have moved abroad. It’s full of humor and wisdom, but I especially love this passage (emphasis mine):

   During my wedding vows, I promised to learn German. Now living here, I’m finally making good on that. My German class has people from all over, including Ukraine, Yemen, Lebanon and Turkey. At first, we were strangers stumbling over introductions. But over time, I’ve been fascinated to see all our personalities shine through while speaking our new language. I think everyone should experience being a foreigner at some point in life. It is completely humbling and makes you more compassionate.

2. Much ink has been spilled on debating the issue of overtourism lately. I have mixed feelings. I do believe overtourism is a problem (especially in cities like Florence where the tourist industry is encroaching on residents’ right to live peacefully—Emiko Davies wrote a great piece on this). Yet I also feel that asking people not to visit certain popular places smacks of elitism and exclusivity, especially when the folks doing the asking are the very ones who have been traveling to and promoting those destinations themselves. Andrew Tuck of Monocle is right on the money in this op-ed (h/t

   Erica Firpo
   of
   Ciao Bella
   for finding and sharing it!):

   Ordinary people, I have a message for you: please desist from booking a foreign holiday. To be blunt, you are cluttering up the world’s cities and beaches, and incensing some locals and a lot of newspaper journalists. While tourism is undoubtedly exacerbating numerous social issues, the reporting of the issue this summer has often been a mixture of naivety and extreme snobbery.

   Do you have thoughts on overtourism? I’d love to hear them.

3. I am a huge fan of Atavist Magazine’s long form reporting and extraordinary storytelling. They recently ran the gut-wrenching story of Layan Albaz, a 14-year-old who traveled from Gaza to the U.S. for medical treatment after losing both her legs in an airstrike. I think I loved it so much because it’s a view of the Gaza crisis that we rarely get to see—this is not trauma porn or a tragedy reduced to statistics, it is the deeply researched story of a girl who wants nothing more than to be a normal teenager, and to have agency in a world that is falling to pieces. This quote will stick with me for a long time:

   In Arabic, the root of the word for “amputated,” mabtur, can mean “incomplete.” This feels like a nod to the idea that it’s possible to sever something so essential to a person that they can no longer be considered whole. Someone who has lost a limb has experienced a deviation from the blueprint of the body; like a novel with chapters ripped out, something crucial is missing.

   In Gaza, all we have to go by are amputated stories, fragments of the whole truth.

I’d love to hear what you think about any of the above articles, and of course, any stories or advice on traveling without a phone or a set itinerary would be very welcome!

See you for our next adventure,
Sam