How I Got Into Solo Traveling

I was 21, living in Chicago, and had finally formed a little crew of adult friends in my new city. It felt like a grown-up milestone — group chats, brunch plans, spontaneous nights out — although looking back, the friendship was definitely rooted in partying and bottomless mimosas more than meaningful connection.

At one point, I brought up taking a trip together — I think it was New York Pride. Everyone was hyped in the group chat. “Let’s do it!” “I’m in!” We planned to book together, make it a whole experience. But as the date crept closer, one by one, people started backing out. Setbacks. Excuses. You know the drill. In the end, the trip fizzled out completely.

I remember sitting there thinking, "I should’ve just booked it by myself and invited them after." That way, if they flaked, I’d still be going. Still having my experience. Even if it meant doing it alone.

So that’s what I did next time. I booked the trip solo. And what started as a workaround became a core part of my lifestyle.

Solo travel hit different. Each trip became its own little mystery — no script, no safety net, just me figuring it out as I went. I talked to more strangers. I tried things I never would’ve if I had the comfort of friends by my side. I was more open, more present. And I started building friendships with locals that gave me real insight into their cultures.

Traveling alone taught me that you don’t always need a squad to have a good time. Sometimes, the best stories start when the group chat fails and you go anyway.