5 Lessons on Travel Planning & Preparation
Prague, Czechia (2014)
Not to toot my own horn (okay, fine, precisely to do that), but I’m a bit of a pro when it comes to planning trips. I’ve figured out that sweet spot between over-planning and under-planning, and the result is that I tend to have pretty fantastic experiences every time I travel—wherever I go.
(As I’m writing this, I’m suddenly feeling a bit wary: you see, I have a trip to Georgia coming up in about a month, and I’m worried that by being too confident on this front, I’m going to somehow end up jinxing myself.)
Of course, that expertise comes from a wealth of experience—including plenty of hiccups, snafus, and mistakes. Not all of these so-called mistakes are things I regret: in fact, sometimes, being an idiot can make for great stories (which, if you’re a writer, are absolute gems).
Listen: my intention with this blog was never to be instructive. I don’t want to tell you how to plan your global adventures, because maybe you prefer to do things your own way; maybe, god forbid, you’d rather book a guided tour and call it a day. Maybe you need to make your own mistakes.
But if you’re willing to learn from mine, I can at least share a few of the lessons I’ve learned along the way—and, even if you learn nothing, perhaps you’ll find some kind of inspiration to glean from them (or at least you’ll get to laugh at my stupidity… so there’s always that).
Lesson One: Learn to love your own company.
Enjoying my own company at Parcul Herăstrău in Bucharest, Romania (2014)
I took my first big solo trip across Europe when I was 20. It was the winter holiday between my semester abroad in Morocco and my semester abroad in Jordan, and traveling back across the ocean for a month just seemed like a wasted opportunity for adventure.
That, of course, isn’t the full story, but it’s the one I use for expediency and because the more honest version is less comfortable. But if we’re going to really get to know one another, dear reader, I suppose I should be fully transparent: you see, it was also the first holiday season after my brother’s unexpected death the previous spring, and the thought of spending a Christmas at home without him was an excruciating kind of pain that I couldn’t even bear to reckon with mentally, let alone endure in actuality. (It would take over a decade before I would spend the holidays with family again—before the holidays became something I could enjoy again. It still smarts, but you learn to forge new traditions and experiences out of the rubble. You learn to carry on.)
Instead of flying home, I packed up my dorm room in Ifrane, took a train to Tangier, a boat to Algeciras, Spain, and the most expensive taxi ride of my life to Málaga, where I dropped my large suitcases off at a friend’s apartment (this friend had agreed to let me store my things with her for the month, but had then been completely unreachable the day of, and it was only through a stroke of utter coincidence and fortune that I’d managed to leave my things with her two frosty roommates).
Exhausted, and frankly a little pissed off that my so-called friend had gone AWOL, I found a cheap hotel and collapsed. I awoke in the evening in a daze, stomach rumbling, having not eaten a thing in about 24 hours. I wandered out into the city and found a small holiday street market, where I bought a baked potato stuffed with a medley of fillings, then made my way to a small park bench and devoured it.
The next morning, I jetted off to Milan and my trip officially began. In those early days, I struggled to know what to do with myself. Wandering alone around foreign cities was disorienting and uncomfortable; dining alone even more so—though, by the time I’d made my way down to Rome, I had gotten better at both, but especially the latter, and to this day, one of the dinners I enjoyed during those days in Rome stands among the most memorable dining experiences I’ve ever had, and perhaps the moment when it all really clicked—the love of solo travel, the love of food, the genuine appreciation for life’s simplest and most exquisite pleasures.
Siena, Italy (December 2007)—somewhere around here, I started to feel comfortable in my solitude
That’s not to say it was smooth sailing from there on out: the boat I took to Tunisia (an effort to bah-humbug myself away from Italy’s Christmas spirit) made me terribly ill, and my first day in Tunis was miserable (and, to be honest, the rest of my days there weren’t much better). But then I flew to Paris to meet a friend, and after showing her around the city, ringing in the New Year at Trocadéro (and winding up at a raucous house party later that night near Gare du Nord), then spending some time in the south of Spain, she departed back to the States, and I was off to Prague, Vienna, Bratislava, and Budapest—once again by myself.
View from a rooftop in Tunis (December 2007). I’d spent the previous day feeling miserably ill, and I lacked the self-confidence to navigate the city solo. That said, I would love to return some day, now that I’m older and wiser
That trip was the start of a steady, gradual shift in my life (one that honestly didn’t fully crystalize until my 30s)—from being an anxious, insecure teen, constantly seeking the approval and validation of her peers, to being a young woman fully ready to embrace the world on her own terms, not needing anyone’s buy-in but my own.
Lesson Two: Do some research, at least. But don’t overdo it.
Florence, Italy, 2007. Not pictured anywhere in my photos or memories: the bloody Uffizi Gallery (and yes, I’m still mad about it)
There are several things that I still, to this day, regret from that first solo trip. The biggest one? When I visited Florence, I failed to go to the Uffizi Gallery. The f*cking Uffizi Gallery! I’ve been back to Italy once or twice since, but I have yet to return to Florence, and I can already tell you the first item on my agenda when I do finally get back there: the motherf*cking Uffizi Gallery. (Over the last decade or so, I’ve developed an obsession with seeing every da Vinci painting I can, and the Uffizi Gallery has three, including one of my favorites: the Annunciation. My all-time favorite can be found in Krakow, Poland: Lady with an Ermine.)
In Vienna, the only places I can vividly remember from that first trip are the Museum of Military History (I’ve since returned, because it’s one of my favorite museums of all time) and Griechenbeisel (a delightful restaurant founded way back in 1447). In Budapest, I visited lots of beautiful places and knew the significance of none of them. I spent a lot of time wandering aimlessly, passing by lots of hidden and not-so-hidden gems, unaware of what I was missing.
The Museum of Military History in Vienna is such an under-the-radar gem—had my parents not urged me to visit that first time back in 2008, I never would have known about it
Of course, these were pre-smartphone days, so my research capabilities were limited to whatever brief time I spent on my laptop while resting in hostels, but that first solo trip taught me that good research is essential if you want to make the most of your time in a place.
That said, there’s a fine line between doing enough research and doing too much, and I think the boundary falls somewhere between knowing what a destination offers and planning precisely what you want to do at every hour of every day. There is nothing drearier and more unexciting than a rigid itinerary—even (especially) the kind that has ‘free time’ penciled in between other fixed and immovable plans. When you’re traveling, all your time should be at your disposal.
These days, I have a trick that works well for me (one that would’ve been unavailable to me back in those pre-smartphone days, but hooray for technology): any time I’m planning to visit a city or town, I create a ‘List’ on Google Maps and start haphazardly adding places of interest: restaurants, museums, cool sites, parks, cute little shops, markets… anything that may or may not be a place I’d like to visit. And then I just play it by ear: I’ll start wandering and occasionally check the map to see what’s nearby.
My Prague list on Google Maps comes in handy every time I visit. Also, Kantýna is an amazing restaurant, and their Dinner from the Butcher is a must for meat-lovers
The map is not an instruction manual: it’s simply there for suggestions. Often, I’ll just stumble upon some interesting place and dive in to check it out. If I like it, I’ll add it to the list on the map (so that I can remember it, either for future visits or to recommend it to others). If a local recommends a particular spot, I’ll add it to the list.
When doing research, I have a few go-to tricks: first, and perhaps this is clichéd, but I’ll check if Anthony Bourdain (RIP) ever featured the destination on an episode of No Reservations or Parts Unknown—and I’ll go watch it.
Fun fact/brag: In 2018, on my first trip to Luang Prabang, I had the opportunity to take a cooking class with a family featured on the Laos episode of “Parts Unknown”
Then, I’ll look for blogs written by immigrants or expatriates living in the destination. I prefer these to the travel bloggers who have simply passed through (LOL, don’t worry, I haven’t missed the irony of me writing this) because they can strike a nice balance between total outsider (who knows nothing) and total insider (who’s like the fish in David Foster Wallace’s “This is Water” speech).
I’ve also been known to peruse books from local authors—either fiction or narrative nonfiction—because literature can be an insightful lens into the soul of a place.
Lesson Three: If you’re going to over-research anything, make it transportation.
Al Hejaz Railway Station in Damascus, Syria (2009)—no, it’s not operational (don’t worry, of all the logistical errors I’ve made over the years, I was at least educated enough not to make that one)
Remember when I said that I took the most expensive taxi ride of my life from Algeciras to Málaga?
Yeah, that’s what happens when you don’t research your transportation options.
Or you wind up wasting a bunch of time trying to navigate foreign subways. Or you have to beg a security guard to let you crash on the floor of a train station in Madrid because the next train doesn’t depart until early the following morning. Or you waste a day at the airport in Phnom Penh because you failed to realize that your dumb American ass needs a visa to enter Vietnam (not to mention having to buy a new plane ticket and spending a bunch of extra money on an expedited visa).
I did eventually make it to Ho Chi Minh City, Vietnam—just in time to catch this gorgeous sunset from the top of Bitexco Financial Tower
Logistics matter, and there’s nothing worse than wasting unnecessary time or money because you failed to educate yourself on the details of getting from Point A to Point B. Also, if you’re like me and you like to avoid standing out as an obvious tourist, understanding the local transportation systems can make you look more local (and thus less likely to be a target for scammers and pickpockets and the like). I can’t tell you how often I get asked for directions or bus/train schedules in foreign countries when I’m standing at a bus stop or in the metro or in a train station. You don’t necessarily need to know where you’re going, but it’s good to know how to get around.
Lesson Four: “Hello” and “thank you” can get you pretty far in any language.
As much as I love Oscar Wilde, I must disagree (quote found on the menu at phil, a great café and bookstore and all-around cool hangout in Vienna, Austria)
It doesn’t matter if the place I’m visiting is a popular tourist destination where English is universally understood: I will always learn at least a few words and phrases in the local language. Most important is “thank you,” because you’d be amazed at how useful a bit of politeness can be. All your encounters will vastly improve if you learn how to say “hello,” “good morning,” and “good day.” And learning a few basic numbers can’t hurt, either—at least one through five.
I do happen to have a bit of a knack for imitating accents, and learning just a few words in the local language means that—at least for interactions that don’t require much depth or follow-up—I can fly right under the radar and blend in a bit. But even if you suck at languages and accents, locals will usually appreciate the effort. Risk the mispronunciations and reap the rewards.
Lesson Five: Spontaneity is where the magic happens.
I owe this gorgeous sunset to the spontaneous decision to spend some extra time on the island of Don Khon in Laos (2018/2019)
On that first solo trip around Europe, I met a group of British-Pakistani guys in my hostel in Budapest; they were in town for a stag party. One night, after I’d already returned from an amazing dinner across town, I got to chatting with them once more, and they invited me to join them on a hunt around town for a halal restaurant. (In Budapest, in early 2008, that was no simple quest.) As I said, I’d already eaten dinner, and could very well have headed off to bed right then and there, but I liked the idea of wandering the streets at night (which is something I tend not to do solo—though, these days, that’s mostly because I’m a morning person) with this lively group of lads. (Worth noting: I’m a fairly good judge of character, and these guys seemed like stand-up gents—and they were.) It took hours to find a halal restaurant, but in the meantime, we got to see a great deal of the city, streets glistening under lamplights, everyone joking and laughing all the while. The restaurant we found was terrible, and I was thankful I’d already eaten my dinner earlier, but it was an evening I’ll never forget.
The food was sub-par, but the company was great (Budapest, Hungary, 2008)
Once, in Marrakech (while I was still a student), I jumped on the back of a stranger’s scooter after he invited me to have ftoor (i.e. iftar, i.e. to break the fast during Ramadan) with his family. Admittedly, on the entire drive out to his family’s flat, I couldn’t help but wonder if I was about to be murdered, but to my delight and relief, I was welcomed warmly and graciously by his family. The next day, on the first day of Eid Al-Fitr, his mother and sister invited me back for lunch, and we spent the afternoon chatting, laughing, and trying on a variety of djellaba.
On the island of Don Khon, in southern Laos, I was beckoned over to have lunch with a family on the first day of the New Year. Despite the fact that I was still overcoming a serious bout of food poisoning, I accepted the pork, roasted peppers, sticky rice, and beer they offered me. I ended up extending my time on Don Khon, and every time I would cross paths with the patriarch of that family, he would invite me to have a beer with whomever he was sitting with at the time.
An unforgettable afternoon with a lovely family on the island of Don Khon (Laos, New Year’s Day, 2019)
Most recently, a spontaneous excursion to Dubrovnik allowed me to indulge in one of the best meals I’ve had in ages (which you can read about in my previous blog post). On my upcoming trip to Georgia, I’ve booked hotels for the first five nights of my trip (two in Tbilisi and three in Stepantsminda), but not for the last two: I’d prefer to see, in the moment, where I want to go and what I want to do.
On this point, I can’t help but think of a quote from Oscar Wilde’s De Profundis: “People whose desire is solely for self-realization never know where they are going. They can’t know. In one sense of the word it is of course necessary, as the Greek oracle once said, to know oneself: that is the first achievement of knowledge. But to recognize that the soul of man is unknowable, is the ultimate achievement of wisdom.”
I don’t mean to imply that travel is solely for the purpose of self-realization: this is, after all, how we end up with throngs of self-centered white women running off and ‘finding themselves’ through Eastern spiritual traditions, all while wearing tight-fitting yoga pants and completely disregarding local customs and sensibilities and, ultimately, the true spirit of the traditions and religions they claim to embrace. But just as trying to know oneself requires being open to anything, getting to know a place requires the same.
When I embrace spontaneity, when I choose to live in the moment, that is when I feel most alive, most connected to where I am, and most connected to myself. That is what travel is all about.
“When one has weighed the sun in the balance, and measured the steps of the moon, and mapped out the seven heavens star by star, there still remains oneself. Who can calculate the orbit of his own soul?”