Born on St. Thomas, Kimmoy Matthews was raised visiting families on neighboring islands, including St. Kitts. While some people dream of resettling to a tropical island to spend the rest of their lives, Kimmoy decided the world was too big to spend in paradise forever, so she booked a ticket to Spain as soon as she graduated and has lived a life traveling the world ever since.

“My love for traveling grew as my interest in the Spanish language grew while in high school. I loved it so much, I spent four years studying Spanish and even became a part of the Spanish Honor Society.” In Spain, she studied for a semester and had the time of her life.

Fast-forward a few years and many travel experiences later, Kimmoy is now a part of the Remote Year Program. “For a very long time, I wanted to take a year off to travel the world, but for the most part I only saw college guys doing it. I started learning about travel hacking and was obsessively reading about people who pursued their travel dreams. I started a savings account so I could do the same too. Once I saw the Remote Year Program on Twitter, I jumped on the opportunity right away. Out of 50,000 applicants, I was selected to join, so I couldn’t pass it up!”

This unique program sets up arrangements for its members to spend a month in different cities so that they can experience twelve different cultures for a year long adventure. “It’s a lot of fun, crazy, insightful, liberating, humbling, mind-blowing, tiring, frustrating, inspiring, unforgettable, all those wrapped into one.” These month long stays have seemed too long, too short, and just perfect depending on where. Kimmoy thought Cavtat, Croatia, a beach town, was a little too long; Istanbul, Turkey, bursting with culture, was not enough, and Ljubljana, Slovenia was a perfect balance. She’s currently in Kyoto, Japan.

Of all her experiences abroad, it’s difficult for Kimmoy to pick just one favorite, but if she had to choose one… “I would have to say Istanbul because there was so much to do there, lots of sightseeing, great nightlife, lovely cafes to work from, boat rides to the Asian side of the country, the culture, food, the hot guys, the Turkish delights!”


Out of this Remote Year, Kimmoy’s newest venture was formed, Lingo Travelers. “[It] is an immersion program designed to get you conversational in a new language while traveling. You spend one month learning to actually speak the language, which is completely different from just reading and writing it. In this program, we take the lessons outside the program and apply them to real-world and fun, cultural activities. For example, before a sultry tango lesson, you’re going to learn how to say ‘step to the right, turn to the left, etc’ in Spanish so that your experience is that much more rich.”

“I came up with the idea because I knew I wasn’t the only one who enjoyed learning the language of the country I’m visiting. It’s really hard to become conversational from apps, Google Translate, and even video courses. I wanted to create a hands-on program that fostered and inspired actual conversations…”

In conjunction with where she’ll be in the last four months of her Remote Year, Lingo Travelers will take place in Buenos Aires, Montevideo, Santiago, and Lima so that Kimmoy can be hands on in establishing the programs. This passion project hearkens way back to her high school days studying Spanish in St. Thomas. She describes it as the stars aligning.

And considering Kimmoy has had quite the experience living and traveling abroad, she has some awesome tips for your next trip. It seemed criminal to not pass all of them on or to try and break them up, so here they ALL are:

  • It’s perfectly fine to book a spontaneous trip, but take it just 1 step further and book your stay for the 1st night. You don’t want to be scrambling trying to find a safe place to lay your head and your belongings. Give, yourself some time to regroup for whatever adventures you’re going after.
  • Definitely learn how to read maps especially if you don’t have access to wi-fi. Getting lost is part of the fun, telling taxi drivers exactly where to go is the annoying part of your job, unfortunately. 
  • Lastly, plug into communities of interest (i.e., fellow solo travelers, study abroad students) so that you can connect with more locals. For example, each month I have been connecting with fellow digital nomads at co-working spaces each country so I stay inspired to achieve my entrepreneurial dreams.
  • Stay aware of the cultural differences and nuances of where you are: everything from crossing a scooter-laced street in Vietnam to separating your own trash in Kyoto to drinking beer anytime of day in Prague. At times it may be strange or annoying, but respect it and soon you’ll learn to see the beauty in it.
  • Don’t expect everyone to speak the language that you speak or have a menu in your language or have the same customs as you.
  • Instead of running through a travel checklist, try to engage and meet with as many locals as you can, whatever experience you share with them will stay with you forever.
  • Downsize your luggage to less than 20kg. It makes traveling that much more easier, cheaper, and faster. Trust me on that one.

What do you think of Kimmoy?! Check her and Lingo Travelers out here:

Personal Website | Lingo Travelers | Facebook | Twitter | Instagram

Interview by Samantha, Photographs by Kimmoy

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