Before November 2025
The idea to do a multi-country—or perhaps world-tour—motorcycle trip began during my first time backpacking in Asia in the autumn of 2024. I learned how to ride a scooter, falling in love with the freedom it allowed. I would rent a scooter in every town I stayed in to do day trips and give myself the freedom to do what I wanted.
After three months traveling by bus and train in Vietnam and Thailand and renting scooters by the day, I wanted a different experience for my final stop, Cambodia—to travel with all of my things by motorcycle. I first considered renting, but no one would let me pick up and drop off in two different cities. The idea of buying a bike crossed my mind. What began as a search for advice on how to buy one quickly became my first purchase.
Over the next two weeks, I traveled from Battambang to Phnom Penh. It was thrilling—on my own in a new country, following roads I found on satellite view in Google Maps. I explored small towns, met locals, and got off the beaten path. I had the time of my life but was quickly called back to my corporate job in New York, which had just secured an office. This adventurous side of me was put on pause.
Fast-forward a year: after more time working my corporate job, we were again without an office, giving me the space to finally bring my love of motorcycles and riding to America. In September of 2025, I decided to get a license and buy my first motorcycle in New York. I told myself this would let me practice my riding so that one day I could take a long trip. After getting my permit and completing an exam and a rider's course, I was fully licensed. Now, to buy my first bike.
I wanted something that would build my on- and off-road capabilities and allow for weekend trips out of New York City. Browsing Craigslist for a bike that was cheap and not too large or powerful—a starter bike—I stumbled upon a few listings for Royal Enfield Himalayans. I had never heard of Royal Enfield, but they were better priced than Hondas and seemed to have everything I wanted in a bike. With help from ChatGPT and research on forums, it seemed to be a great beginner bike at a great price.
I reached out to one of the listings on Craigslist and managed to meet up with Peter in Great Neck, Long Island. When I arrived, I saw a beautifully maintained 2018 Royal Enfield Himalayan in Snow (gloss white). After not riding for a year—and having used a clutch-based manual motorcycle only once before—I was very nervous that I would be unable to ride away. In the words of The Alchemist, the universe finds a way to help you when you are following your personal legend. Peter turned out to be a motorcycle riding instructor and stayed with me late into the night in the parking lot by his house until I was comfortable enough to ride away on my own!
With a license and now a bike, I was ready to practice and ready for what came next. In November, my job needed to reduce headcount, and the operations team—myself and one other person—was being cut to a single seat. I felt this was my opportunity to get out. To get out of what seemed like a life I would not enjoy: office life, operations work, the slog of New York. In that moment, I looked toward greener pastures.
During my last week of work, I began to plan what would become a crazy idea: riding my Himalayan through Mexico, Central America, and South America to Ushuaia, the southern tip of South America.
And just like that, I was off…
