Episode #386: Traveling Cuba Offline, Hiking Rainbow Mountain & Human Connection in Guatemala with Kylah Williams

Episode Summary

Learn how solo travel, living abroad, Spanish fluency & cultural immersion unlock deeper connections around the world. 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 experiences.

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Kylah Williams

Kylah Williams (“That Bilingual Chick”) is a bi-lingual world traveler and cross-cultural marketing expert. After getting a Masters Degree in Marketing, a Fulbright, and working for the New York Times, she now specializes in the cultural nuances of advertising to different Hispanic and Latino communities.  Originally from Sacramento, California she grew up in an African-American home, became fluent in Spanish through immersion, and has lived in Chile, Mexico, and Spain.  She now runs immersive trips to Spanish speaking countries, creates bilingual content that teaches Spanish through bite sized lessons, and she is launching the Convo Club—a language learning community where virtual sessions are centered around a trending TV show, album, or book—making practice fun, engaging, and culturally rich.

What You'll Learn
  • How to turn language skills into a global career
  • Why intentional travel experiences create deeper human connection
  • How to navigate solo travel across cultures with confidence
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Time Stamped Show Notes

**Click the time stamp to jump directly to that point in the episode.

[1:20] Getting a Fulbright to Live in Mexico City

[4:22] Living in Mexico after Being Immersed in Mexican Immigrant Culture in the U.S.

[6:19] Deepening Her Interest in Cross-Cultural Marketing

[7:39] Learning Different Dialects Across Spanish Speaking Countries

[9:49] Sao Paulo, Brazil

[13:35] Hiking the Rainbow Mountain in Peru

[19:12] Kylah’s 2027 Group Trip to Peru

[20:51] Visiting Guatape and Paragliding in Medellin, Colombia

[27:32] The Dominican Republic

[30:09] Visiting Cuba with No Data Plan

[33:54] Connecting with a Local People in Guatemala

[36:24] Connecting with Marginalized Communities Around the World

[39:00] Building Her Brand as “That Bilingual Chick”

[42:04] Language Learning Tips

[47:14] The “Convo Club” Language Learning Community

[49:15] How Travel Has Impacted Kylah

[50:17] Connecting with other Black Travelers

[51:37] What Travel means to Kylah

[53:40] The Lightning Round

[57:59] Follow and Connect with Kylah