The peripatetic Airbnb co-founder talks about where his travels have taken him: estuary destinations, jiu-jitsu academies, Japanese Buddhist temples, and Disneyworld.
Let’s play spin the globe—name the one place you’ve always wanted to go.
I’d hope it lands on an “estuary destination,” or one-of-a-kind environments that don’t exist anywhere else. These places, located where two different cultures converge, are fascinating and inspiring to me—cities like Chuy, which sits between Uruguay and Brazil, or areas like Andorra, between Spain and France.
What’s your spirit city?
Tokyo. As a designer, the city speaks to me. It has a culture of refinement of form over embellishments, integrity of materials instead of superficial ostentation.
Do you have a travel ritual?
When I travel, I usually look for an anchor, a physical object that reminds me of a feeling or emotion I experienced during that visit. They can be anything from incense to sketches.
Do you maintain any routines from home while traveling or does it all go out the window?
While traveling, I do make time to keep up with my jiu-jitsu. I’ve been lucky to train around the world in Cuba, Rio de Janeiro, Miami, and Beijing.
Sorry, you only get to eat one regional cuisine for the rest of your life. What is it?
I can’t choose just one, but I could eat grilled cheese and tomato bisque forever.
Describe your travel personality in three words.
Curious, adventurous, off-piste.
Are your trips very planned, or very spontaneous?
Very spontaneous. I love moments of discovery that are found by getting lost or letting a local be your guide.
What’s the one travel souvenir you’d save in a fire?
The monk I stayed with in Japan gave me a meditation cushion from his Buddhist temple, which I cherish. Buddhism teaches you to not be attached to material objects like this, but I still think I’d grab that because it reminds me to sit and just be each day.
What book/movie most inspired you to travel?
I don’t know if there’s a specific movie or book that sparked my travel bug, but I do know I was inspired by my dad. Growing up, I heard stories of his adventures hitchhiking from England to the Middle East. I specifically remember him showing me foreign coins and thinking for the first time that there were other places in the world besides home.
Who’s your ideal travel partner?
The sun.
Which travel experience do you prefer: plugged in or unplugged?
As a founder, it’s difficult to be completely unplugged while traveling. However, one of my favorite travel experiences was when I stayed at a Zen Temple in Oita-shi, Japan. During the stay, I took on the monastic lifestyle, including morning prayers and meditations, exploring nature and enjoyed the simplistic pleasures of the remote temple.
What’s a custom from another culture that you’d love to implement in your life back home?
In Japan, it is customary to take your street shoes off at the door and put on slippers for the house. I loved the custom so much that I adopted it in my own home. In fact, I’m wearing some now.
What’s the first thing you seek out in a new place?
I like to go to the local market to experience what people from the area really eat, and jiu-jitsu academy so I can train with locals.
What’s the one thing you indulge in on a trip that you don’t at home?
I draw more. Without my phone and computer on hand as easily, I find myself using pen and paper much more, which I love.
What’s your first travel memory?
Funnily enough, it was Disneyworld. My parents took me there when I was really young and recall the warm air, the grandeur of the park, and the sound of Space Mountain.
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