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An Oh-So-Seasoned Traveler’s Guide to Flying Solo

BY liz 04/20/2017

Jennifer Stilwell is an old hat at traveling alone—like, she’s been at it since childhood. Her parents separated when she was a kid, and she would regularly go back and forth between her mom’s home in Argentina and her dad’s place in the States. “One parent would take me to the airport and deposit me on the plane, and the other parent would pick me up on the other end. These were never direct flights—once I had a 15-hour layover in Chile,” she remembers. Those formative early days shaped her lone-wolf approach to the international jaunts she plans to places like Oaxaca whenever she can get away from her L.A. studio, where she hand-sews sturdy and striking leather and canvas bags. Here, her seven tips for joining her in going at it on your own.



“As an adult, I have realized that I do horribly in groups. I want to do what I want to do, when I want to do it, and I don’t really want to compromise with my time when I am on vacation. In an ideal world, you meet someone who has the same travel goals, and then you end up having an awesome time—but more times then not, I have not had success traveling with other people. For this reason, I fly solo.”



“One of the huge pros of being alone is that you get to organize your own time. If you want to sleep in and do nothing, no one is going to give you any shit. If you want to be a weirdo and wander the streets until 3 a.m., you can. I have so much energy when I am traveling and want to see so much everyday that I end up walking eight to ten miles a day, which is not for everyone. At the end of the day, my feet always hurt, and I am truly exhausted but have a giant sense of accomplishment. I feel like I always discover so much about the town that I am in in a way I don’t if I’m taking cabs or hotel shuttles everywhere. I ask a ton of questions, I dip into all the stores, and I take pictures of everything.”



“One of the drawbacks of traveling alone is the need to self-motivate and plan. Sometimes two heads are better than one, especially when it comes to coming up with ideas of things to do. Someone else you’re with may have done more research than you, or may have been tipped off to something really cool that maybe you wouldn’t have known about otherwise. I try to work around this by doing a ton of research before I leave and then talking to anyone I can find once I get there—whether it’s in the local bar or the grocery store.”



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“I think solo travelers are more likely to stay in hostels where they can bounce ideas off other people, but I always prefer stay alone so I’m not at the mercy of anyone else. My preference is also to have an apartment instead of a hotel room, so I mostly use Airbnb—but sometimes you can get really lucky by asking on Facebook if anyone knows of good spots to rent.”



“When I travel, I travel really light. I know that if I run out of toothpaste, I can buy it. If I need an extra pair of socks, I can buy them. I view it as sort of a treasure hunt because if I have to find something simple, looking for it is a great way to see a bit of people’s everyday lives. I love stopping inside hardware stores, pharmacies, kitchen-supply stores—almost everywhere except for the tourist shops. But I do always bring a few essentials that are very personal, like a bathing suit. It doesn't take up much space, and you never know when an opportunity to take a dip might present itself. And I'm not a huge runner, but sometimes it’s the best way to get the adrenaline of being alone in a new place out—and you can do it anywhere. So I always take a throwaway pair of shoes—plus I like to be prepared for a forest walk or a hike!”



“One thing I always do is find my local bar. After a full day of being on a nature tour or climbing to temples or running around in the waves, I like to unwind with a drink. I love looking at people’s fashion and the way they interact and flirt with each other, and I’ve found it also allows me understand the place I am visiting a little better. Nightlife observations are really helpful!”



“When I get to big cities, I usually spend the first day feeling utterly alone and somewhat panicky, like a total outsider. Those are times I wish I was with someone. But generally, once I power through that first day, I am happy being on my own again. It’s a great way to get to know yourself better! I just wrapped up a trip to Chiapas and Oaxaca, Mexico, and I met so many people because I was alone and just ready to start convos with anyone. And being alone in Chiapas, I found myself just staring up at the trees a ton and discovering all the different bromeliads that grow there. I didn't really care about bromeliads until this trip, I don't think I would have taken that time just study them if I had been with someone—it’s hard to talk if you are constantly staring up at the sky.”

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