Vacationer of the Week: Courtney Vondran

Courtney Vondran will quickly tell you that they are a proud Midwesterner born in Davenport, Iowa, and raised in the suburbs of Chicago. Currently, a resident of the LGBTQ+-friendly Windy City, they are on a mission to find the queerest neighborhoods in the world!  

It will come as no surprise to fellow vacationers why we jumped at a chance to connect with the successful genderqueer content creator, who offers a few pearls of wisdom to solo lesbian and queer travelers, who enjoy slow travel. 

Vondran provides insight into how a transformative trip to Brazil completely changed the trajectory of her life and explains why you should be open to visiting places that may not be on your radar as LGBTQ+ friendly.

Vacationer Magazine: At what age did you receive your first passport? What was your first trip? 

Courtney Vondran: I got my first passport when I was 18 for a trip to Cancun, Mexico with my best friend and her parents. I just remember there being buffets, unlimited alcohol, and a twerking contest at Senior Frogs.

What trip or travel experience sparked your passion for travel? 

I studied abroad during my last year of college in Florianopolis, Brazil for three months. We got a week break in the middle and I decided I wanted to take my first solo trip. My friend helped me book a hostel for the first time on hostelworld.com. 

I remember it was a 14-bed dorm for $7/night in Copacabana, Rio de Janeiro. It was a quick walk from the beach. What really sparked my travel bug was the people I met in that hostel. I met a middle-aged Israeli woman who quit her job to travel the world for “I don’t know how long” and an Irish woman who traveled the continent of Africa from the southern to the northern tip by herself. 

I know it’s a bit cliché, but that experience 100000000% changed my life. My Midwestern, middle America reality was altered forever, and no one could tell me that travel was expensive or that you had to have a 9 to 5 job. I saw with my own eyes ordinary people who were doing something different.

Before that trip, I planned to graduate with a business management degree and work in human resources, perhaps recruiting. After my trip, I called my parents and told them I was going to backpack the world. About a year later, I quit my job and took my first solo trip which led to an eight-year ‘anti-sabbatical’.

Please tell us how you identify yourself on the LGBTQIA spectrum. Tell us if how you identify influences the way you travel. If so, how? 

I identify as a genderqueer lesbian. Before I came out, I was broke in my 20s, looking for a way to travel in the cheapest possible way. I came out at 29 (almost three years ago) as a lesbian.

Now, I prioritize traveling to “extra” LGBTQ-friendly destinations. Destinations that go above and beyond to make queer locals and travelers feel safe and celebrated. Places with gayborhoods, lesbian bars, queer-owned businesses, queer events, and queer people. One of my most recent trips with my partner was to Campit, an inclusive LGBTQ+ outdoor resort in Michigan. I felt relaxed and at ease. All the feelings everyone wants to feel when they take a vacation. My fiance, Liz (they/them), is trans nonbinary and masc presenting—looks very queer. Their safety is something I consider as well.

Is there a travel destination that most queer travelers would think isn’t safe to visit, but you’ve visited and enjoyed it? If so, where? 

Liz and I just took a road trip from Chicago to Chattanooga, Tennessee to visit their sibling who just moved there. We stopped in six cities on the way there and back. I was nervous going to the South, but it was so gay! The highlights for me were the gayborhood in Indianapolis, Gay Street in Knoxville, and the lesbian bar in Nashville, the Lipstick Lounge. It was a necessary reminder for me that everywhere is queer. Queer pockets are sprinkled around the world even in Tennessee.

You’ve done quite a bit of traveling on your own backpacking through Central and South America. What advice would you give to lesbian or queer travelers who may be considering exploring the world solo? 

Solo traveling is one of the best gifts you can give yourself. Don’t let your great aunt who has never traveled to other states tell you that Guatemala is too dangerous. It’s beautiful. Just trust your gut and go where you are pulled to go.

You’ve created a community of explorers. How long did it take to build up a strong following, and how would you describe the travel style of this community? 

It took years and years and years. I started my blog nearly 10 years ago with three readers; my mom, my dad, and my best friend. My community has grown exponentially since coming out and focusing on LGBTQ+ travel. So much so, that a year ago I was able to go full-time as a travel creator. 

I would say my community’s travel style is the kind of traveler who will eat at a hole-in-the-wall and stay at a boutique hostel in Vietnam or enjoy a highly rated 5-star meal downtown Chicago for the experience. We prioritize queer-owned, local businesses. We’re also excited about finding a lesbian bar or a local queer event while traveling. Think of us as the bed and breakfast traveler who enjoys slow travel more than seeing everything.

You talk about “pivots as signs from spirit” on your blog. What does that mean to you? Is it the guiding force for navigating the world? 

To me, it just means following your gut. Everything always works out somehow, some way. I never in a million years thought I’d be engaged living in Chicago’s gayborhood with two cats and a dog, getting paid to travel and talk about gay stuff. There are rainbows on the other end of life’s shifts and pivots.

What are three things LGBTQ+ travelers should do when visiting your hometown or the place where you currently live, which I believe is Chicago, correct? 

Yes. Go to the Gerber Hart Library, our queer library (tell them Courtney sent you). Explore thrift and local shops in Andersonville aka Lesbianville. Grab a drink at Dorothy, the lesbian bar. If you have time, check out the Leather Archives and Museum. If you like to party, go out in Northalsted aka Boystown, or at least go for a meal at the Chicago Diner at the Northalsted location. 

Looking for more to do in Chicago, check out Courtney’s blog post of 101+ gay things to do in Chicago. Her website also has a free gay Chicago map with 170+ queer-owned businesses in Chicago for travelers to use. A link to the map is located in the blog article mentioned above.

What are your top three favorite places to visit? Why? 

Colombia for its music, dancing, and colorful culture. Puerto Vallarta, Mexico for its beauty, queer scene, and food. And Spain for its food, people, and gorgeous architecture. 

What three places are still on your bucket list to visit? Why? 

I’m on a mission to visit all the gayborhoods in the US. The three that I would love to visit next are all the gayborhoods in New York City, San Diego’s Hillcrest neighborhood, and Provincetown, Massachusetts. Internationally, I’d love to go to South Africa, Argentina, and Amsterdam. I’ve heard good things about all of them from fellow queer travelers.

What’s one thing you never forget to pack in your suitcase?

I have this oversized thrifted Harley Davidson t-shirt that is my “comfort t-shirt” that I always travel with. Nothing is better than slipping into comfy, familiar clothes at the end of the day or on hard travel days. As a neurodivergent traveler, I try to pack a couple of different comfort items in my suitcase that ground me.

You’re going on a road trip or a long-haul flight. What singer or band is always on your playlist? 

Neither. I’m usually listening to podcasts about cults and scammers.

You can keep up with Courtney Vondran’s travels by following them on TikTok, Instagram, YouTube, Facebook, and X (Twitter).