
Santa Cruz Walking Tours
Hidden History, Culture, and Stories—Led by Local Guides


Trusted by travelers with 12+ five-star reviews
Choose Your Tour
"Tours are relaxed, entertaining, enlightening, and highly recommended for anyone seeking a bigger, more flavorful slice of Santa Cruz history."
Guests Love Our Tours!
⭐⭐⭐⭐⭐ 12+ five-star reviews on Google, Airbnb, TripAdvisor & Viator
Questions? Call or text us at 831-275-2566

Meet Your Guide
Matt O'Leary leads history and culture walks across Santa Cruz—from the coastline and Beach Hill to downtown, the old Mission site, and surrounding Victorian neighborhoods. Each walk explores a different layer of the city, from its surf heritage to its early development and architectural character.
A Santa Cruz surfer since the late 1970s, co-founder of The Juice surf magazine, and a competitor in the O'Neill Coldwater Classic, Matt pairs firsthand knowledge of the local surf scene with a deep interest in the people, places, and events that shaped the city both along the coast and in the downtown historic district.
"Matt has extensive local history to share and also invites hearing stories from other locals and visitors." — Alison, Google ReviewMore About Matt →
Ready to Book?
Pick a date to see available tours & times
Full refund if cancelled 24+ hours before tour start time
Calendar not loading? Book directly on FareHarbor →
Your Tour Includes Exclusive Local Perks
Enjoy discounts and special offers from favorite Santa Cruz shops, cafes, and downtown businesses. Each partner sets their own offer and redemption window.
Show your tour confirmation email to redeem.
Same-Day Perks

MyTOQUE
Free 100 ml olive oil with $25 purchase

Moon Kissed
10% off
Within 3 Days

Mythic Games
Free Magic: The Gathering welcome deck + 10% off

Super Silver
Free crystal gift with $10+ purchase
Within 7 Days

Hidden Peak Teahouse
15% off

Artisans & Agency
10% off

Nicely
10% off, including existing sales

Mission Hill Coffee & Creamery
10% off
Do you own a Santa Cruz business interested in getting more foot traffic?
Join our local partner network — fill out a quick form and we'll be in touch.
Apply to become a partner →Planning for a Group or Team?
Make Your Next Offsite Unforgettable
Walk Santa Cruz designs custom tours for startup retreats, corporate offsites, and remote teams meeting in person. Genuine exploration of a remarkable city — the kind of experience teams will reflect on and talk about for years to come.
Plan a Corporate TourWant the Full Experience, Your Way?
Fully custom walking tours for solo travelers, couples, families, groups, or teams. Your interests, your pace, your Santa Cruz.
Design your tour →




