How (and Why) to Travel Solo

Illustration by Giacomo Bagnara

One time on a business trip to Stockholm, I had a day to kill. I didn’t know what the hell to do so I just started walking around the city’s interconnected islands — over this bridge past some cartoonishly perfect old buildings, over that bridge to a green expanse that put Central Park to shame. After my hours-long aimless stroll, I got hungry. I binged a few cinnamon buns, browsed vintage stores for home goods and records, had a leisurely dinner and, some time, after midnight ended up at a club where I met a few criminally attractive blondes and a Skarsgård spilled a drink on me. My point is I did whatever I wanted — something that’s near impossible to do if you’re traveling with someone (and not a complete ass).

These days, I’ve come to prefer traveling alone. I’ve stayed up ‘til five playing video games in Japanese arcades. I’ve splurged on extravagant meals but also ate nothing but baguette and local cheese. I’ve bought rail passes and blindly pointed at maps because why not? When you’re rolling one deep, any ridiculous whim is yours to follow.

Of course, not all solo destinations are created equal. Unless you’re looking to search and destroy some personal demons, don’t plan a solo romp somewhere remote. You want a city that is large enough to get lost in with incredible food (hello, 9 million residents of Mexico City) or one that is novelly offbeat (think midnight sunlit adventures in Reykjavik) or one full of rowdy, chatty locals who might strike up conversation and buy a round of shots (just say g’day to anyone in Melbourne). The addictive thrill of traveling alone is being reminded at every turn that life is full of infinite possibilities, so go in with a curious mind.

Daytime is easy — just wander and pack a book — but if you’re unsure where to start a night, do this. Get dressed up in an outfit that can go any which way (say, a blazer, tee, and dark jeans), head down to the bar of the local cool hotel, and chat up the bartender for some food and drink recommendations. These folks are usually suspiciously clued in. Make sure to dine somewhere with bar seating, made for those who want to sit alone with a phone and battery pack and not feel like a goon. If you’re really stumped, book a ticket to a local show — an over-the-top opera, a film festival screening, a rock concert at whatever cool-kid venue. There’s plenty to enjoy on your own and you’re surrounded by locals, who are likely drunk and chill, so much so that they may strike up a conversation and adopt you into their clan.

Or just head to any other drunken space where people have let their hair down. You’re alone and therefore more likely to attract casual conversation. One time in Sydney, I overheard two guys at a pub debating American politics and weighed in. Fast-forward five hours later and they, off-duty bartenders, had taken me to a Texan-Australian honky tonk, a speakeasy with outrageous cocktails, and a punk venue with killer pizza. They’re still some of those folks who pop up every year on Facebook on my happy birthday, which is to say I have a place to crash next time I’m in town.

If talking to a stranger IRL sprouts hives though, just do what you do at home and get out your phone. Swipe, chat, and explain to the human on the other side you’re only there for a short window of time. You’ll probably find most souls enjoy helping out a stranger passing through and will freely pass along recommendations, even without the expectation of meeting. Or, if the vibe is right, well, you know what to do from there.

Andrew Richdale