A Semi-Comprehensive Breakdown of My Biggest Travel Regrets

If you’ve read any of my other posts, you know my (somewhat accidental) journey into this lifestyle has been wrought with regret and rookie mistakes. Behind every humble-brag Instagram photo is perhaps a sleepless night, a bout of food poisoning, a lonely cry with my hostel bunk curtain closed, or some narrow death-escape that sounds way cooler after the fact.

Every year pre-pandemic, I’d come back to the US for the holidays and scratch off another few countries on the basic AF (but secretly appreciated Christmas gift) scratch map hung on my childhood bedroom wall, maybe make an emergency hospital visit, begrudgingly throw away all of my gear in order to appease my bedbug-paranoid parents (or hide it all in the bushes down the street), and cry over some sort of whirlwind travel fling.

The routine gets old just like any other, but it keeps me entertained while I pretend my entire life isn’t built around 9-5 existential dread. I began drafting this post ten months into 2020, restlessly hiding out in Guanajuato, Mexico and anxious about the future of humanity/the safety of my family/my canceled-until-at-least-mid-2021 career. I couldn’t help but think back on all those adventures in the ever-distant past and fully prepare myself for the post-vaccine world where I right every wrong I’ve ever made and #LIVE #LIFE #TO #THE #FULLEST. Really though.

With that in mind, here’s a semi-comprehensive list of my worst travel mistakes and biggest regrets, more or less in order of increasing consequence. I hope my lessons learned the hard way help you avoid the some of the growing pains of your own. Also, Content Warning: TMI.

And without further ado let’s talk about

Swallowing Lake Water

While volunteering in San Marcos La Laguna, Guatemala, I developed a massive crush on this French dude with a buzzcut and obsession with old motorcycles. Aside from our penchant for Type 2 Fun, we had nothing in common outside of our mutual disdain for all the hippie gringos swarming the village. One morning, he fashioned a wooden paddle with his ~mad carpentry skills~ and took me on a romantic paddle board ride on Lake Atitlán, where I proceeded to immediately crash into the water and swallowed a cesspool of protozoa while gasping for air. I got a classic Guatemalan parasite and spent the next two months with dysentery, completely forgetting I’d brought along a course of antibiotics in my first aid kit, prescribed by my doctor as a safety measure against…this exact situation.

I ended up with a few souvenirs: a several-thousand-dollar ER bill (which I spent all of 2020 fighting for my insurance to cover), ten pounds of muscular atrophy, and, well, my fully-stocked first aid kit for next time. But all those months of hyper-vigilance against getting even a drop of tap water near my mouth? As usual, anxiety was a waste of energy. (You might see a pattern emerge in this post.)

Not Using Legit Bug Spray

Hear me out—

1) DEET is banned in several countries. If I’m going to be in the tropics every day for months, that’s a lot of neurotoxicity in my bloodstream.

2) Before my first solo backpacking trip, I’d doused all my belongings in DEET out of fear I’d get bed bugs in the hostels. DOUSED. Like actually unscrewed the spray cap and POURED it all over my sleeping bag, backpack, jacket and boots. And at my second hostel in Europe, not only did I get bed bug bites on every inch of my body, but I woke up to a dozen of them crawling all over my sleeping bag like little death-resistant mutants (They are). So, you know, maybe not worth the health risks.

So here’s what I did in Central America instead: I bought overpriced, all-natural bug spray made with no more than a few essential oils. It smelled amazing and did absolutely nothing. My mistake became utterly apparent after a short hike to a waterfall one morning, and the subsequent three weeks I spent unable to sleep because the bites covering my legs like chicken pox from this particular species of tiny blue Guatemalan mosquito kept me up all night, every night. I came back to the US with little white scars all over my calves, and a resolve to listen to locals next time.

Not Splurging on Top Priorities

When I started backpacking regularly, it was more out of necessity than anything else.

I’m a performer. I work in theatre, which means in order to maintain anything resembling a career, I need to post up in a major city—and not just any major city, but a city with a considerable professional theatre scene (cheaper art hubs like Portland and Atlanta don’t make the cut).

Do you know how much it costs to live in a theatre hub in the US? A lot more than I typically make. You know what costs a lot less than Trying to Make It? Getting to peace out between gigs. Let’s take a look at the math:

Rent: roughly $1000/month (a little more for the San Francisco Bay Area, a little less for Chicago, but that’s about average for a US city where theatre exists substantially enough to sustain a livelihood).

vs.

Housing + food + sightseeing + adventures abroad on a backpacker’s budget: roughly $1000/month total (sometimes slightly more, sometimes a lot less).

See my logic? I can spend my year hustling, staring at lists of audition notices and submitting cheesy pictures of my face, singing to strangers and once and a while booking work that actually pays the bills for a few months, all the while working other jobs to make ends meet…or I can take work as it comes, leisurely submit to projects that actually interest me, focus my energy on strengthening relationships with specific companies I admire, and travel the world in the meantime.

But what does all this mean for the experience of actually traveling? It means I have a strict budget. Just like any other life setup, there are sacrifices involved. I don’t always get to do and see everything I want, and that fact especially sucks when I’ve made it all the way across the world to some ~*amazing*~ location. But alas, long-term travel is not one continuous honeymoon, and I’ve compiled a pretty long list of poor choices over the years as I’ve gotten to know myself and my values through these experiences. Most of my regrets may be unrelated to finances, but sometimes I secretly wish I weren’t—to quote my ex—such a Capricorn.

Here are a few things I wish I hadn’t been so $avvy about:

- Not taking free walking tours in several cities with fascinating histories I knew nothing about just because I was afraid I couldn’t afford to tip the guide.

- Not going inside anything in Vienna except two churches and a single art museum. I know I’m an ignorant plebeian but I still could have appreciated melodramatic world events with 15 € and an audioguide.

- A Frida Kahlo exhibit in Prague for which I giddily waited in line for an hour before checking the ticket price ($30) and leaving. Easily spent $30 on good-but-not-great restaurants within the next few days.

- Not bringing more cash to the Kite Festival in Sumpango, Guatemala so I wouldn’t splurge on food. Instead, I chose to pack a free brownie and a dry Spanish tortilla from the hostel where I was staying and passed up all the most mouthwatering, cheap as shit dishes during this once-in-a-lifetime experience.

Which directly leads to my next regret:

Ever Spending Money in the US

That’s it. Pretty self-explanatory. You get used to 20¢ avocados and then never want to buy another avocado at home ever again.

And fine, if my friends back home want to grab dinner once in a while, I’ll oblige. But if I’m given the choice between a $20 sandwich in the Bay Area and delayed gratification for the novelty of delicious (and almost always cheaper) food from a cuisine I’ve never tried? Come on.

The same goes for any form of entertainment. Outside of seeing my friends’ performances, I can usually forgo that movie or cover charge if it means entry into Dorne or a cathedral so beautiful I’m crying through the entire audioguide or a fancy meal in Bellagio after three days of protein bars. It all depends on your interests, of course. A gentrifier making my coffee does not interest me.

I know this bullet point in the list is a big privilege yikes, and I fully acknowledge the financial benefits that come from not owning a car, being able-bodied enough to easily walk 20,000 steps a day to cut down on public transportation costs, and not having a consistent roommate or partner or kids or other family members who rely on my presence and income. As long as this all remains the case, I’ll stick with my rent-controlled studio sublet with shitty water pressure and get out of the US as soon as possible.

Country Counting

For my legendarily sophomoric second solo backpacking trip, I decided to squish eleven countries into a span of two months. My itinerary was as follows:

• Iceland - 8 days

• England - 3 days

• Ireland - 4 days

• Czech Republic - 4 days

• Poland - 5 days

• Greece - 4 days

• Turkey - 7 days

• Hungary - 7 days

• Czech Republic Again - 3 days

• Austria - 3 days

• Belgium - 1 day

• France - 2 days

Needless to say a few unforeseen circumstances interfered with this ten-years-delayed gap year. There’s nothing quite like planning a whole day of sightseeing in Athens and then spending the entire time drowning bed bugs in a laundromat again before rushing to catch a plane.

This 600-countries-in-6-days backpacking habit came to a head when I impulsively quit my volunteer position in Guatemala to jump on the back of a motorcycle for a “dream” road trip. We spent only two days in each Central American country while some of the most beautiful places I have ever seen in my life flashed before my eyes as we sped past them; some days too time-crunched even to stop for pictures (aka evidence of my cool life for Instagram).

Should I have declined the offer to See! The! World! simply because it wasn’t my ideal timeframe? Of course not. But the "torture" of beauty dangled just out of reach certainly shifted my priorities. Travel is still real life, and real life comes with inevitable compromise.

I do think there’s a way to avoid compromising too much, though: a one-way ticket and a commitment to exploring wherever you are slowly enough to really appreciate it.

I know slow travel rarely a viable option for us Americans and our nonexistent PTO, and I’ve frequently fallen into the trap of overbooking my short break from work and watching my mental health unravel on ~vacation~, but if you’re lucky enough to have time at all, use it wisely.

Stop country counting (Leah) and treat your first time in a new place like a first date—dive in too quickly and it implodes, but let it slowly burn and the foreplay is nothing short of magic. Allow your infatuation to transform into something deeper. Your photos/stories/battle scars will be better for it.

(After spending months in a COVID hideout Airbnb in Guanajuato, Mexico, I can confidently say slow travel has won me over. Well…stagnant travel, to be more accurate. Huge accommodation discounts for long-term reservations is only one of the many perks. Getting way better at the language is another. Making more than passing friendships, feeling safe and comfortable wherever I am in the city, finding tons of great food outside the tourist areas, actually getting to live a calm and low-drama life…all more upsides to not having a chaotic itinerary with no time to spare.)

Not Examining My Internalized Racism and

Almost Getting Deliberately Poisoned

For my 30th birthday at the beginning of 2020 (the Before Times), I gifted myself a two-week, four-country backpacking trip inspired by an impulsive nonstop ticket purchase to Oslo for $159 (Thank you, Kiwi.com). At the end of those two weeks, I crashed at a friend’s apartment in Paris and spent a few days stuffing my face with croissants while walking from one end of the city to the other, without making much of an effort to avoid the tourist traps. One night walking through the 1st arrondissement, I noticed how strange it was to see the plaza of the Louvre nearly empty (again: pre-COVID universe). I stopped and took a picture. I now regret that choice.

A tall white man in a cardigan walked past me carrying a briefcase. Mid-thirties, nice haircut, scarf around his neck. Nothing out of the ordinary in this area, minus the sight of a local walking through the Louvre plaza at all. He did a double take and stopped, said something to me in Spanish with a thick Parisian accent, and I thought, Hey, why not? I’m losing my Spanish anyway. Maybe he’ll even be patient enough to let me practice French.

After chatting for a few minutes in a mishmash of the two languages, he invited me to a wine bar, and the fourth red flag popped up when I politely declined because I don’t drink. (The second: his alleged age being exactly what I told him mine was and the third: his alleged occupation as a boulanger—because sure, who doesn’t wear slacks and carry a briefcase to and from the bakery?)

He immediately jumped into peer pressure mode like we were in a D.A.R.E. commercial. I remember thinking to myself, Dude…aren’t you a grownup? But after a few harsh shutdowns he pivoted and offered a late-night coffee date instead.

I hesitated, and he felt it. But as I’ve spent the last couple of decades regularly navigating creepy strangers, I knew it would be safer to walk somewhere with more people and more light. So I said yes, and we headed toward the Seine.

“This is a shortcut,” He mumbled in French, heading down the stairs straight to the river.

Great, I thought. This is how I die.

Then he sat down on a bench overlooking the water and pulled out a pair of bulky headphones, patted the seat next to him and said, “So beautiful. I want to show you my new favorite song. It’s perfect for a night like this.”

Feel free to judge me when I say I put the headphones around my ears and sat there for an entire four minutes while a sweeping Italian aria drowned out my deafening heartbeat.

When it was over, he pulled out a bottle of rosé from his leather briefcase, the contents glistening as he held it up to the beam of streetlight at our feet. His pitch:

It’s my favorite.

Look at the year.

It’s from le Rhône.

You can drink just once.

It would be such a shame to let this go to waste.

Look how beautiful the Seine is.

You’re so beautiful.

You can’t come to Paris and not have the full Parisian experience.

But I’m a boulanger!

Just a sip. I’ll even have some, too.

Who knows what would have happened if I hadn’t seen Season 1 of Game of Thrones.

Finally I stopped him—

“If I speak English right now, will you understand?”

“…Yes.”

And with a momentary utter disregard for my safety, I bitched him out like a killjoy grandma, all the while speaking as if I had no assumption of anything sketchier than a regular dude who just doesn’t know how to quit.

At the end of my manifesto I stood up to leave and he jumped to his feet to apologize. Then he wrapped his arms around me and tried to…dance? I pushed him away and he held tighter, apologizing again before leaning in for an open-mouthed kiss.

Noticing a couple heading toward us with their dog, I gave my best WHAT THE FUCK IS WRONG WITH YOU scream, as loud as I could manage with his arms still squeezed around my ribcage.

He released me, pulled back, and ran—up the stairs away from the river, straight toward the street, clutching his briefcase and the bottle of wine(?) inside. When I made it up to the top of the stairs, he glanced back toward me before checking all sides, and ran across the street and into the dark plaza of the Louvre.

Now, here’s the thing—If he hadn’t been a white boy in business casual, I wouldn’t have humored him for so long, or maybe even to begin with. I still have no idea what was in the wine—if he was just a creepy guy trying to roofie me or if it was something even more insidious. Either way, it was a big wake up call not only to avoid complacence around my biases and instincts, but to research social norms of the countries I’m visiting instead of assuming America is the norm. I found out later that Parisienne women literally ignore men accosting them in public in nearly all contexts because the level of sexual harassment is so extreme that no stranger is worth anyone’s time. An outsider might see this as one stereotypical example of aloof Parisian culture, but it’s a great reminder that every cultural practice has a reason and context often invisible to visitors. I can’t assume I know what’s up or what’s best or let my well-traveled pretentiousness cloud my sense of wonder and basic observation skills.

Only Speaking English

Flashback to 2004—Mid-argument with my mother in the living room of our house behind the Oakland Zoo. I’m holding up a schedule request form for my freshman year of high school, shouting that I should be allowed to learn whatever language I want. She’s forbidding me from taking anything other than Spanish. My family has already failed me once—it would be racist to let me take French.

But I don’t want to take Spanish, and I’m afraid to tell her it’s because I’m so ashamed of not already speaking the language that I’m paralyzed by fear of outing myself as a “fraud.” So I erase 'French' through tears and spend the rest of high school acing the written homework while cutting class every time conversation practice is listed on the syllabus.

By the end of those four years, I got nothing. No language skills of any kind. In college, I was secretly grateful to pursue a degree jam-packed with other studies that didn’t leave room for the two-year language requirement of other majors. I swallowed my guilt every other day when someone spoke Spanish to me on the street. And when I went to Mexico with my bilingual white boyfriend, I gladly drank the feelings away as I watched the debauchery and cleavage-tequila trick from the safe distance of Cabo Wabo’s top deck.

And then I started traveling on my own, and lost opportunity quickly became necessity, and necessity became desire. Not because of my ongoing identity crisis, but because of other backpacking strangers who I wished I could get to know if only I wasn’t bound by the glass window of my unsurprising American Exceptionalism.

But the fact that the greatest driving factor in my relationship with language-learning was my own childhood baggage reveals that I come from a country privileged enough for me to center myself at all. I felt no urgency to learn any other major world language because I didn’t have to. And, to be fair, I still don’t. As an anglophone, it is absolutely possible to get by in almost every tourist destination in the world without even learning how to say thank you.

And yet, it is the people I meet when traveling who make this chaotic life consistently worth it. Above sightseeing and volcano selfies and sometimes even above street food. Every memory in my private list of top travel highlights involves a new friend. And while I may never get so good at any new language that I can rival the depth of conversation possible with a native speaker, I have butchered my way through enough Spanish and French over the last couple of years to have had innumerable profound interactions with people from whom I would have otherwise been cut off entirely and who have, quite literally, changed my life.

And that’s enough motivation to get past the baggage most days.

Not Learning and/or Following Social Etiquette

You know how after you do something wildly thrilling a million times, it starts to lose its magic?

Example:

On opening night of my first international tour (of a Netflix kids’ show-turned-musical), it felt like just another day at the office. From all my previous ~national~ tours with the same company, I had grown so accustomed to the cacophony of thousands of children simultaneously erupting in giggles at my improvised jokes that I couldn’t even muster enough adrenaline to wake up as the curtain opened. The sound of applause did nothing. A sea of wide-eyed kindergarteners dressed up as mini-versions of us exploding with joy gave me a jaded smile at best.

That’s sort of what traveling is like when it goes from being a spontaneous, brand new and kind of scary one-off endeavor to your primary means of general life avoidance. A week in Panama City becomes an inconvenience. Vienna is...fine. By this point you really just go to Paris for the people (oxymoron?).

But once in a while you find the thing that takes your breath away again. For me—as a quintessentially-shitty American who unintentionally internalized the exoticization of the second-most popular religion in the world—that place was Istanbul. For better and [mostly] worse, I pranced around the city like a jackass for an entire week, falling completely in love with everything ~strange~ and ~foreign~ and ~wow so incredible that this world is so vast and encompasses so many manifestations of the human spirit!~ But do you know what I didn’t do?

Actually muster up some semblance of earnest respect for the culture.

Nor did I give a second thought to what that respect meant. I thought of myself and my Instagram alone.

Example:

Oh? I’m not supposed to wear yoga pants or ripped jeans? But that’s all I brought. Fine. I’ll tie a sweater around my waist, but not because it’s the respectful thing to do, but because if I don’t, I’ll spend the whole week feeling naked as strangers burn holes into my clothing with their eyes.

And fine, that’s fair. As a woman who has lived her entire life on Earth, of course I’m going to be primarily concerned with how not to get leered at or groped in a crowd. It would probably be absurd to expect any other priorities, or to think I wouldn’t have a knee-jerk reaction against the inherent sexism within…hold on let’s count…every major culture on the planet.

But there was no internal sense of reverence for the sacred components of these social contracts, nor was there any sort of nuance to my understanding or my desire to understand. I assumed my values were the objectively correct ones, and therefore didn’t concern myself much with actually learning about the dominant cultures of the area. I simply (resentfully) abided by the rules as they were brought to my attention.

So—with nothing but the best of intentions—I embarrassed strangers, unintentionally hit on waiters, barged in on male spaces, insulted new friends, and took up a lot of public space in that iconic American way. In other words, I tokenized a culture I knew essentially nothing about for the sake of my infatuation with it.

What could I have done instead? More research prior to the trip, with a focus toward how to move through the country gracefully rather than as a gawking ✨experience✨ consumer.

Relying on Others

On Easter Sunday 2019, my are we or aren’t we…seriously let’s not again ex and I sat on the grass of Milan’s Parco Sempione recovering from a huge Italian brunch and a long night of petty arguments when a little blue notification popped up on my phone announcing that our Blablacar driver had canceled last minute.

I did the math and realized that if we didn’t make this seven-hour drive back to France, we’d miss our flight to Morocco which would domino effect and screw over our Airbnb reservations in several cities as we made our way through the country to visit my friend in Taroudant. We’d lose a ton of money, and all my months of Morocco-obsession and research would be for nothing.

On the other hand, I thought, this might be the universe doing me a solid. Just as I’d relied on a stranger through the Blablacar app to get us to Marseille from Italy in a timely fashion, I’d invited my moody ex along to Morocco because my French still didn’t come close to his native fluency and, well, I was afraid of traveling alone in a country where women regularly get groped in crowds. My whole setup only worked if we didn’t ditch each other.

In the end, we failed to find another way to catch our flight without spending far more than our budget allowed, so we cut our losses and picked the cheapest Flixbus ride we could find—arriving at 5am in Ljubljana, Slovenia. It ended up being the highlight of our trip, but the whole stress-filled experience leading up to that decision taught me a few things:

1. Don’t rely on strangers for important deadlines.

2. Don’t rely on unstable people to provide stability.

3. If I’m not going the spontaneity route, I better leave room for error.

And, really, it may have been the best mistake I ever made.

Letting My Ego Get the Best of Me

Let’s review:

There was the time I got a parasite in Guatemala and thought I could cure it with kombucha and chewed up papaya seeds and ended up with a $2000 ER bill.

The time I thought I could camp at high elevation during a European spring with nothing but a windbreaker, hoodie and hammock and nearly lost my toes.

The time I didn’t train whatsoever before scaling 5000 ft in 20 miles in 8 hours with 30 extra pounds on my back.

The time I didn’t think to research road signs in Iceland before embarking on a solo road trip.

…Then there was the time I thought I could bring an active alcoholic to a Muslim country for a picture-perfect vacation.

…The time I thought it would be fun to tag along on a trip to Mexico with my boyfriend while he was mid-opiate withdrawal and smuggling a 5 oz bag of weed past Border Patrol dogs.

…The time I got lost by myself in the Costa Rican jungle during a thunderstorm.

And my favorite: the time I thought I could master a new language in a few months with no more than Duolingo and French rap.

You get the picture. My ego is a liability. I have learned how to survive this lifestyle purely through trial, error, and a shit ton of luck. It may sound absurd considering my utter lack of common sense, but I am a hardcore pre-trip researcher. And yet if you don’t know what questions to ask, you can still get into trouble whether or not you’ve mentally prepared for a handful of possible scenarios.

Traveling is like any other life skill—people who don’t understand what it takes to learn how to do it well will assume it comes naturally. In all my humbling (re: humiliating) experiences, this idea couldn’t be further from the truth. Whether you’re flirting with the notion of throwing your life away in lieu of a 9-5 rebellion, figuring out how to do the whole digital nomad thing, or simply want to strengthen your skillset when it comes to spontaneity, get comfortable with the idea that no adventure—even the most meticulously-planned one—goes 100% smoothly. Your limits will be pushed, the space outside your comfort zone will feel both exhilarating and awful, and your ego will do whatever it can to ruin your trip.

That’s all I got. Get vaxed, go forth and compile your own list, and don’t forget to report back.