About Your Guide

Hi! I'm Matt O'Leary, and I grew up in Santa Cruz and have spent countless hours exploring the beaches, redwoods, and neighborhoods that make this area so special.

Over the years, I've developed a deep appreciation for studying the history, architecture, and natural surroundings of the Santa Cruz area. What began as casual walks with friends has grown into a passion for sharing what I've learned — helping visitors and locals alike discover the hidden gems and stories that make this place unique.

My background in design and writing informs every Walk Santa Cruz tour — the pacing, the details, the story arc. I've also taught surf lessons both casually and professionally, and I enjoy spending time outdoors with family and friends — whether it's hiking to waterfalls and ocean views or urban exploration. That same spirit of sharing what I love inspired me to start Walk Santa Cruz.

I believe the best way to experience this place is on foot — it's a healthy, fun way to slow down, take in the scenery, and connect with the stories and landscapes that define Santa Cruz.

We look forward to walking with you soon! Feel free to reach out if you're interested in private tours or team offsites.