How to Do Debauchery Without Dying: Solo Travel and the Art of Finding Trouble

Now, I’m a very femme woman. I’m 5’3”. I wear four-inch heels to the airport (which is smart, because they’re heavy and take up a lot of space in luggage, so of course, I wear them to the airport). And I have a habit of walking in places where people like me could easily disappear. I have a face that makes taxi drivers ask if I’m “sure I should be out this late,” in the same tone that hotel concierges use before they write their personal number on the back of the city map “just in case,” and I can fit into luggage with shocking ease. I’ve got my privileges, to be sure—but I have been told many times, by many people, in many languages that I am inexplicably “kidnappable.”

This was not news to me. In fact, I had been wondering for years how I’d made it this long in life without ending up in a basement. It’s a miracle no one pulled up next to me in a van in 2003 offering candy because I was so happy, round, and naive, my only question would’ve been: “What flavor?”

And still— I travel alone, walk home alone late at night, and listen to music on the subway. Am I fearless? No, I’m stupid, but still, I can count on one hand the number of times I’ve genuinely felt unsafe. There’s a difference between brave and reckless, and baby, the sweet spot lives somewhere between doing Molly you bought from a cab driver in Ibiza with a group from the hostel (brave) and crossing against the light in Rome without checking for Gay tourists on Vespas (reckless).

Ciao, bella— straight to il hospital.

Before I went on my first trip alone, I was at my office job, luggage stuffed under my desk so I could leave at 4:45 and head straight to JFK. I went around and told everyone I wouldn’t be back—to their relief. There are only so many times you can misprint a PDF before people start to wonder where your parents went wrong. They all wished me well and hoped I’d have a good trip, and when they asked me what I hoped I’d get to do while abroad, I’d shrug and say:

“I don’t know. Have good food. Buy a hat. Maybe get a little kidnapped— but in a fun way.”

They’d all balked at this, and I’d had to explain that I thought it might happen anyway, so I may as well preempt it. Besides, my father had told me that the one thing I was not allowed to do was get into any stranger’s car, boat, or plane, which immediately made it the #1 thing I was aiming to do. This explanation didn’t seem to help much besides perhaps making them grateful for whatever stage of life their daughters were at and the fact that they weren’t where I was yet (I didn’t have the heart to tell them that someday, they would be). Yes, the day I left, I think they were very relieved indeed.

I’ve never been one to shy away from an adventure— one day I’ll write about the 19 months my family refers to as “Electra’s Year of Living Dangerously” — but adventure at home and adventure abroad have two different tastes. And I have to admit taking a liking to trouble across the pond relatively quickly.

So there are certain things to bookmark when you’re alone in a foreign country, and there’s a perfect amount of risk to take. But if I had to shortlist the things I learned, here’s what I know:

  1. Learn how to search for bathrooms on the go. You only have to almost-shit-yourself-in-front-of-la-segrada-famigila once before you bookmark that search in maps. You’re traveling, you’re trying wonderful foods you’ve never had before. Most people see God in the church. I saw her in the porta-potty just beside it. You could say my prayers were answered, but I’m pretty sure at that point I’d abandoned all faith. I wish I could say the street food wasn’t worth it, but sadly, I’d still do it all over again if you gave me the option. Some sausages are worth the sacrifice, and read that with whatever entendre you will. Don’t be a diva, pack Imodium, and remember there are no heroes after adventurous eating.

  2. Prepare to break your shoes, or your feet, or both. Walking shoes this, and walking shoes that— look, a walking shoe is a state of mind. A Wedge is a walking shoe with the right attitude— which is my attitude. There is no excuse for tennis shoes unless the excuse is plantar fasciitis, a hot-butch kind of vibe, or sneakers that serve cunt. Diana got away with it, so I can’t speak in totality, but if you’re ruining a perfectly good outfit with a flat and citing “cobblestone streets” as your out— I’m afraid you’ve misread the handbook. That said, don’t overplay your hand. When my walking heels broke and I was forced — forced—to spend four straight days in 5-inch platform gladiator heels that laced all the way up, I realized that maybe, just maybe, I’d made an error in judgment by bringing “solely” (pun) less than sensible shoes. So don’t be afraid to wear a heel (it’ll blow the American off you for sure), but pack a pair of comfort shoes… just in case.

  3. Bring a Performative Purse Book to dinner. Not to read. God, no. Everyone knows you can’t read. You’re going to set it gently on the table, next to the Aperol Spritz you’re still learning to like (the Hugo Spritz is better, it took me too long to learn that), where it catches the light just enough that someone passing by thinks she’s mysterious and well-read and possibly French— oh! an exposed nipple! She’s definitely French! It should be something slim but literary, like Joan Didion if you’re wearing black, or After Leaving Mr. MacKenzie if you’re wearing red, or The Fountainhead if you’re trying to repair a broken relationship with your father. Suppose it has dog-eared corners, even better— it should look like it’s been handed to and back from a lover who didn’t understand it or you. The book becomes your companion, and it makes dining alone feel less like a date with Elijah and more like a scene from a black and white movie.

  4. Accept the favors. The other benefit of a purse book? You’re 1000% more approachable than when you’re buried in your phone— but you still have an escape for any skeevy joiners. “What are you reading?” can be a ten-second or ten-minute conversation, and it’s entirely up to you. I’ve had lovely older couples buy me several rounds at outdoor bars because they remembered their days of traveling alone, and wanted to hear my stories. Ask the waiters what their favorite bar is, and when they tell you their friend works there, drop their name at the door. Get the free drink (when you’ve witnessed its making). The concierge giving you her number for a midnight drink after her shift? Save it. The middle-aged couple at the café inviting you on their boat tour? Accept, and stay on for as long as you can swim to shore. You are allowed to be gracious and elusive. One woman’s “taking candy from strangers” is another’s “learning to trust the kindness of humanity.” And besides, saying yes is how the good stories start. But for the love of god, trust your gut. Mine was well tuned from years of city-living, people-watching, subway-surfing. I was raised to count the risks and the exits. If the vibes are off, abort. If not? Get on the yacht.

  5. Have people to call. Bother them. Solo travel does not mean radio silence. It means you now have a rotating cast of friends to wake up at 3AM New York time so you can narrate your grocery store adventure in London. They will be annoyed. They will get over it. People secretly love being your lifeline when you're far away—it makes them feel like the “person back home.” And anyway, when you’re traveling solo, you’ll need someone to verify you’re not hallucinating when you almost shit yourself in front of the Sagrada Familia for the first time. If all else fails, call your parents; they’ll be thrilled to know you aren’t dead. Or vlog. Anything to fill the void and cocktail hour.

  6. Get Home Safe. There’s no hard and fast handbook for this. You’ll hear stories of people who got on boats with random strangers in foreign countries with dead phones and absent sobriety who made it out with nothing but new friends and a great story (guilty). And you’ll hear stories of people who were just walking home and just didn’t make it. The times I have felt the most unsafe have always been the times I had been taking the least risk. Checking into hotels. Trying to leave cabs. Oftentimes because it was when I least expected something to go wrong. Keep your wits about you, and stay safe.

Now, I know this all sounds contradictory. Wear the heel, but pack the sneaker. Be spontaneous, but smart. Flirt, but only in two languages or less. And maybe that’s the real lesson here— solo travel forces you to be more than one person at once. Which is probably why it sits so firmly in my core beliefs of Doable-Debauchery. There were days I felt absolutely uninhibited and 1000% alone in the world… until the second I felt an ounce of uncertainty, and— my god— I was shocked at how quickly I was able to snap back to attention. It was as if my better half was monitoring the whole time without me even knowing it. You develop a sixth sense for exit signs, sketchy men, and whether the wifi at a restaurant is going to ruin your night (and it almost did, but the paella saved it).

You’ve started to realize this isn’t advice so much as a diary— or maybe a confession. Your Honor, I rest my case for the nearly long-gone and, yes, the evidence is heavily redacted. But in my efforts to— what was it I said before? Oh yes, “preempt” the danger I knew I was meant for by trying to go out and find it on my own terms— I learned less about how to find it than I did about my ability to survive it if I ever did.

Traveling alone drastically changed my belief in my ability to survive and thrive in any one of the different lives I could choose to live. Whether I was standing on the subway platform in New York, or at the top of a hill in Florence, or on a beach in Cyprus, or alone in the shadow of the Acropolis with my broken shoes and my fake book and my too-heavy heels, I felt absolutely in control of the chaos I was causing.

I never did tell the office I left before that trip that I achieved my goal of getting (lightly) kidnapped. But I think the mystery of it is half the fun.

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