
386: Traveling Cuba Offline, Hiking Rainbow Mountain & Human Connection in Guatemala with Kylah Williams
From The Maverick Show: Global Travel Stories & Life Beyond Borders by Matt Bowles: Full-Time World Traveler Since 2013
April 27, 2026 · 1h 4m · Episode 386
About this episode
Kylah Williams discusses her experiences with solo travel, cultural immersion, and the impact of Spanish fluency on her global career.
Learn how solo travel, living abroad, Spanish fluency & cultural immersion unlock deeper connections around the world. ============================ Get the Monday Minute my weekly email with 3 personal recs for travel, culture, and living beyond borders you can read in 60 seconds. ============================ ON THIS EPISODE Kylah Williams shares how she transformed Spanish fluency into a global career and a deeper way of experiencing the world. From traveling through Cuba without data to forming meaningful human connections in Guatemala and pushing her limits on Peru’s Rainbow Mountain, she reflects on how solo travel and cultural immersion reshape the way we see people, identity, and belonging. Kylah shares stories from living in Mexico City and lessons from navigating cross-cultural marketing and the nuances of Spanish dialects around the world. She explains the evolution of her platform “That Bilingual Chick,” and shares her experiences connecting with Black traveler communities globally. She also reflects on how stepping outside her comfort zone—from everyday interactions to adrenaline-filled moments like paragliding in Colombia—can unlock deeper, more meaningful travel…
People in this episode
Host: Matt Bowles
Guest: Kylah Williams
Topics covered
- solo travel
- cultural immersion
- Spanish fluency
- human connection
- travel experiences
Keywords
- Cuba
- Guatemala
- Rainbow Mountain
- Spanish fluency
- cultural immersion
- travel
- human connection
- Kylah Williams
Mentioned in this episode
Organizations: That Bilingual Chick
Places: Cuba, Guatemala, Peru, Mexico City, Colombia
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