No Maps, No Mercy: The Gospel of Solo Travel

There is a certain grim suspicion that follows the solo traveler. The pitying glances from airport bartenders, the raised eyebrows from desk clerks, the unspoken yet palpable curiosity from couples who wonder if you have been recently divorced, fired, or otherwise cast adrift from the safe confines of polite society. The assumption, of course, is that solitude is a symptom of failure—that if you were truly worth a damn, you’d have a wife, a posse, or at the very least, a misanthropic travel companion to endure your quirks and proclivities for the sake of camaraderie.

This, of course, is pure horseshit.

To travel alone is to rid yourself of the chains of compromise. To move without the molasses-like drag of obligation, of one person’s need for midmorning coffee clashing with another’s appetite for a 7 a.m. hike, of an art freak and a pub-crawler playing passive-aggressive chess with the itinerary until both wind up miserable. Traveling with one other person is a negotiation; traveling with a group is a hostage situation. The dream of perfect travel chemistry is just that—a mirage. Even your best friend will eventually grate on your nerves, and by day three, you’ll be fantasizing about shoving them into the nearest canal.

Let’s talk about fitness: some like to storm through a city like they’re being chased, racking up 15 miles a day on foot, relentlessly pursuing some half-baked ideal of adventure. Others prefer the languid pace of a cafe philosopher, nursing an espresso and a cigarette, watching the world pass by in a haze of caffeinated enlightenment. Mix these two species and what you get is a misery parade, one person exasperated by the endless sitting, the other cursing their burning calves, both silently wishing the other would die in their sleep.

Patience, compromise, and tolerance—the pillars of group travel—are also the wet sand that buries your trip in the suffocating weight of forced politeness. A single weak link in the chain—a whiner, a control freak, a delicate constitution incapable of stomaching the local cuisine—can transform a dream vacation into an exercise in diplomatic restraint. You will bite your tongue, swallow your frustration, and spend the bulk of your expensive, hard-earned getaway ensuring that someone else’s experience is going exactly as they wish, while yours drifts into a pile of unfulfilled ambitions. You will return home exhausted, frustrated, and unable to remember why you even wanted to go in the first place. The photos you took from the trip will inspire only rage.

Which is why, one Monday morning in the halcyon days of the late-1990s, with my brain still soaked in the cheap liquor of the weekend, I found myself clicking a link for a Net SAAver fare from Chicago to Stockholm. American Airlines had just unleashed this beautiful experiment: last-minute international flights at grotesquely low prices. The catch? You had to leave within a few days. Every Monday, a fresh menu of absurdly cheap destinations would arrive in my inbox like a dare, and on this particular morning, I took the bait. I knew absolutely nothing about Sweden—less than nothing, really. On my way home from work, I stopped into a bookstore and grabbed two travel guides, skimming their pages like a man cramming for an exam for which he hadn’t attended a single lecture.

By Friday morning, I stood in Stockholm’s T-Centralen station, blinking in the early autumn sunlight, wondering what in the name of God had just happened.

What happened was freedom. Real, uncompromising, untethered movement. No debates over where to eat, no agonizing over whether we should do the tourist thing or hunt for something “authentic.” Just me, the city, and an unspoken agreement to figure it out as we went. I walked until my feet burned, wandered into bars with no plan, ate strange foods without a translator, and absorbed the raw, electric pulse of an unfamiliar place without the filter of a fellow traveler’s expectations. I was hooked.

Since then, I’ve prowled solo across Europe, through Canada, and all over the U.S. with no real blueprint beyond a plane ticket and a place to sleep. I’ll glance at TripAdvisor or Reddit for the basics—don’t walk down this street at night, eat here, avoid there—but beyond that, I prefer to let the city unfold on its own terms. Every place has its own scent, its own rhythm, from the buttery warmth of morning bakeries to the acrid bite of exhaust curling through the streets. You don’t get that from a neatly planned itinerary. You don’t get that from haggling over dinner choices or from cramming into an Uber because someone in your group refuses to walk another step. You get it by sinking into the flow, letting the city take you where it wants, one impulse at a time.

Something else happens when you travel alone—you meet people. Whether it’s out of necessity or some strange magnetism that solo travelers possess, the world tends to open up in unexpected ways. When you’re the only one responsible for every interaction, you engage more. Locals notice, they ask questions, they offer advice, sometimes a drink, sometimes an invitation to something that isn’t in any guidebook. I’ve been lucky enough to forge friendships that have lasted well beyond the confines of a trip—people who now rank among my closest, dearest friends. There is something about meeting someone in a foreign land, unburdened by the assumptions of home, that allows for an honesty and depth rarely found in the everyday shuffle of life. It’s never the goal, but it’s damn near impossible to finish a good solo run without a fistful of phone numbers, email addresses, and a string of photos capturing moments that wouldn’t have existed if I hadn’t gone it alone.

That’s not to say I’m against traveling with a partner. A well-matched companion—particularly a romantic one—can add a dimension of joy that solo travel can’t touch. There is something undeniably satisfying about sharing a dish so exquisite that you both stop mid-chew, eyes widening in mutual revelation. And when the chemistry is right, the dance of discovery is even richer, each new experience magnified by shared wonder.

And yes, there are group trips that work—Formula 1 weekends with a crew of like-minded degenerates, where the chaos is the point. But these are exceptions, rare alignments of attitude and energy that make the collective experience worth the sacrifice of autonomy.

But give me a week, a dog sitter I trust, a valid passport, and the scent of adventure in the air, and I am out the door. No plans, no negotiations, no dead weight. Just me, the road, and whatever madness lies beyond the horizon.

The friends we meet along the way. Stockholm, 1997.