Adventuring Alone: The Case for A Solo Weekend Trip

I pulled open the door to the dimly lit sushi joint, smiled, and walked up to the hostess. She looked at me, then beyond me, then at me again. “How many?” she asked. I answered the same way I had answered for the past two days: “Just one. Only me.” From my table for four, I stared out the window at a city now mostly asleep. This dinner, the whole evening, was secretly a celebration. I had taken on a challenge, a dare-to-self, and succeeded: the past two days in Chicago had marked my first real solo trip.

Let’s begin with definitions. By solo trip, I mean a deliberate choice to enjoy a journey and destination without traveling with anyone or scheduling any meetups with friends. Of course, you might make new friends in the process, which is part of the fun. Traveling alone doesn’t have to be for the broken-hearted, melancholy, or anti-social. And it doesn’t have to always be a statement about independent womanhood either. When done well and for the right reasons, braving the mountains, a new city, or the seaside alone can be a healthy part of a holistic, well-centered life. (And you can even do it if married.) 

Pulling off a solo trip is easy. Set a budget, pick a place, and write a basic list of diversions, both new and familiar. Research events and attractions ahead of time so you can buy tickets if necessary. Pack lightly, leaving enough room for shopping if you’d like. Tell friends and family where you’re headed and where you’ll stay. Once you arrive, take a walk, rent a bike, or jump on the train and explore. Tourist attractions are fun, but try also to explore neighborhoodsthere’s nothing more rewarding than stumbling upon a lesser-known local haunt. Set goals for each day: reach the lake, hike a mountain, attend a workshop. Tuck in a few personal goals also like journaling, writing a new song, or taking a handful of unique film photos. Notice when the solitude “gets to you,” and instead of running from or resenting it, try to lean deeper into it.

Traveling alone isn’t meant to be the same as traveling with friends. You might feel odd at first, a bit as though you’re drifting at sea. You might panic at the thought of ordering food or a drink alone or discover that you don’t quite have the courage to enter as many cute boutiques without your trusty partner-in-style. That is okay. Traveling alone isn’t about proving anything to anyone. It isn’t about making a political or social statement. It isn’t about forcing yourself to do things out of your comfort zone. It’s about taking the time to meet yourself, challenge yourself, love yourself, and then offer that centered self in service to others.  

I took a solo trip to Chicago for the 4th of July weekend. At 2:00 p.m., I pulled open the door to Urban Holiday Lofts and rushed up a narrow flight of stairs. The lobby is decorated moderately, in a subdued post-industrial aesthetic, with just the right combination of warmth and austerity. I spent less than $50 on lodging and spent two nights in one of the best hostels I’ve ever seen. Eight women can stay in the “deluxe female dorm” with a private bathroom, a fridge, cute flannel blankets, and exposed brick walls. There’s always someone at the front desk and several coffee shops, grocery stores, and drugstores just a quick walk away.

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To start things off, I left Room 201 and wandered for hours, peeking inside half a dozen thrift stores on Milwaukee Avenue. Three or four hours later, I stopped for dinner at Penny’s Noodles where I grabbed a window seat and worked through another chapter in The Kings of Nonfiction. The Basil Fried Rice, friendly staff, and casual seating area made Penny’s the perfect first solo-dinner stop. I changed outfits and moseyed Downtown to visit The Bean and a free Portland Youth Orchestra performance in Millennium Park. It was the perfect combination of something new and something touristy!

Saturday’s goal was to reach Lake Michigan, but first: coffee. I walked slowly through a very quiet neighborhood, listening to the Lucy Rose album. I read this article on De Blasio’s wife over coffee and an egg sandwich at Red June. On my way out, I stopped at a public bike rack and pleasantly discovered that, for $7.00, I could use a bike for the next 24 hours, in 30-minute installments. I grinned idiotically, chugged down the rest of my coffee, and strapped my bag to the front. For the next six hours, I swerved around town: over the river to Old Town, to the Lake where I listened to a sermon, to  the Zoo (hey monkeys), and to the Natural Museum, which is more for children, but butterfly rooms and live tarantulas never get old.  

Traveling alone is mostly fun, but sometimes sad. Sunday evening, I had made plans with a writer I met at the Symphony, but they fell through. There I was, 7:00 p.m., sitting at a taco shop eating the world’s saddest tacos in an adorable outfit with no one to talk to except a homeless guy who was suggesting I read The Old Man and the Sea. I ignored him at first, but then decided his advice was the best option so far. I found a copy at Myopic Books then turned the corner and decided sushi at the aforementioned dimly lit café was in order. I decided being alone wasn’t so bad after all.

The point of a solo trip is to intentionally enjoy something alone. It’s a chance to wander without a map, eat whenever (and whatever) you’d like, take as many photos as your heart desires (or none at all), and meet new people. Solo travel also has deeper awards. It gives you an opportunity to contemplate, to celebrate personal inner growth, to endure loneliness, fear, and unsureness on your own two feet. It’s a strengthening rite of passage that can help us discover a sense of self that doesn’t depend on the presence or opinions of other people.

I didn’t mind being alone at the sushi restaurant and I didn’t mind it the next morning either when I boarded a boat for the Wendella Architecture Tour. Or when I strolled up and down Miracle Mile and through the J. J. Audubon gallery inside the Wrigley Building. I didn’t even mind it when I decided to order and enjoy a beer alone for the first time. I sat by the window, opened my book, and took slow sips, people watching, thinking, telling all the boys who thought I was sad that I wasn’t. That I was perfectly happy and content. And when they asked if I was alone, I said yes.

And that’s exactly how I liked it.

—Tiffany Owens is a fellow with the Fund for American Studies. As a journalist, she’s currently living on the road, writing about creative economies in four American cities. She favors New York City, coffee (black with sugar), and having friends all around the country.