Meet Brian Benson: Educator, Explorer, and Travel Consultant

“Evolve with Intent” - BB

Brian Benson is a lifelong explorer, educator, and mentor whose career is rooted in experiential learning—whether he’s guiding travelers through Costa Rica’s rainforests, helping teens build confidence in Spanish, or drawing from his past as a professional BMX stunt rider, sponsored snowboarder, mountain biker, and skater. With over two decades of hands-on experience across Latin America and the U.S., Brian brings a rare combination of cultural fluency, educational creativity, and real-world perspective to everything he does.

His journey began in 1997 with a surf trip to Costa Rica—a trip that turned into a 15-year stay. Captivated by the country’s biodiversity, warm culture, and relaxed rhythm of life, Brian dove into the world of educational travel. He spent years developing and leading immersive programs for students, schools, families, and small groups. Today, as a travel consultant, he continues to design custom experiences rooted in connection, curiosity, and local insight—whether it’s a family vacation, a small-group adventure, or a guided expedition for a film crew.

Alongside his travel consulting work, Brian is a Spanish tutor where he specializes in helping pre-teens and teens build a strong foundation in Spanish. Drawing from his time as a high school Spanish teacher in San Francisco—and his years living and working in Latin America—he creates personalized lessons that connect with each student’s interests and learning style. His sessions are high-energy, creative, and relational—designed not only to teach the language, but to spark a lifelong love of learning.

Whether he’s mapping out a travel itinerary or helping a student master tricky verb conjugations, Brian brings the same values to his work: curiosity, authenticity, and a belief that growth happens when we lean into new experiences. Grounded, thoughtful, and endlessly curious, he helps others evolve with intent—and enjoy the journey along the way.

”All my life I’ve embraced adventure and taken on challenges that pushed my limits. These experiences, including my time as a professional BMX rider, sponsored snowboarder, and my ongoing love of surfing, have given me a deep understanding of personal growth through passion, resilience, and embracing the unknown.”

Career Summary & Highlights

  • Brian has spent nearly two decades designing and leading transformative outdoor education programs that combine adventure, personal growth, and academic relevance. His work spans high schools, educational tour companies, and private clients, reflecting a deep commitment to hands-on learning and meaningful travel.

    The Marin School (San Francisco) – Outdoor Educator & Trip Coordinator
    Led immersive wilderness experiences for high school students, integrating environmental education with leadership development. Designed and facilitated multi-day backcountry trips emphasizing resilience, teamwork, and ecological awareness.

    The Bay School of San Francisco – Outdoor Educator & Adventure Coordinator
    Created adventure-based learning programs tailored to a diverse student population. Prioritized safety, inclusivity, and connection to place through well-structured and engaging outdoor experiences.

    Sterne School (San Francisco) – Experiential Trip Coordinator
    Managed all aspects of experiential travel programming, including destination research, risk management, student preparation, and on-trip leadership. Aligned trips with academic goals and supported students with varying learning needs.

    Chill Expeditions (Costa Rica & Latin America)

    • Naturalist Guide / Outdoor Guide: Led student and adult groups through Costa Rica’s national parks, rainforests, and coastal ecosystems, delivering rich ecological and cultural experiences.

    • Costa Rican Branch Manager: Oversaw logistics and in-country operations, trained guide teams, and collaborated with schools to create custom learning journeys across Central America.

  • Sterne School (San Francisco)
    As a Spanish teacher at this private, student-centered high school, Brian brought language and culture to life. Drawing from years living in Latin America and leading bilingual trips, he created a vibrant classroom environment rooted in curiosity, empathy, and real-world relevance. His approach emphasized communication, trust, and creativity—earning the respect and engagement of diverse learners.

  • Beyond student-focused trips, Brian has provided personalized Costa Rica travel consulting for over a decade—planning and coordinating trips for couples, families, film crews, and small groups. His deep local knowledge and attention to detail allow him to create unforgettable experiences that balance adventure, comfort, and cultural authenticity. Whether it's navigating remote national parks, curating family-friendly itineraries, or guiding a film crew through protected rainforest terrain, Brian ensures every trip is seamless, immersive, and tailored to the travelers' goals.