Santa Cruz
Walking Tours
with Local Guides
Hidden history, culture, and local stories
Trusted by travelers with 12+ five-star reviews
Choose Your Tour
UCSC Digital Archives / Herry Mayo Collection
Surfing & Beach Culture Walk
Discover the exact spot where mainland surfing began in 1885. Led by a surf magazine co-founder with 45 years in the water — and designed to be unforgettable.
- Best for: surfers, ocean lovers, first-time visitors, and anyone who wants a story they'll always remember
- Duration: 90 minutes
- Schedule: Thu–Sun, 10am
- Price: $45 adult · $30 child · Kids 5 & under free
Heart of Downtown Santa Cruz
The original Walk Santa Cruz tour. A story-rich journey through downtown streets, local architecture, and the history and character of the city locals love.
- Best for: first-time visitors and shorter outings
- Duration: 90 minutes
- Schedule: Sat–Sun, 1pm
- Price: $45 adult · $30 child · Kids 5 & under free
Beach Hill to Downtown Santa Cruz Loop
Beach Hill's grand historic estates plus the Victorian, Craftsman, and Art Deco streets of downtown — neighborhoods worth experiencing in a whole new way.
- Best for: deeper exploration and history lovers
- Duration: 90 minutes
- Schedule: Thu–Fri, 1pm
- Price: $45 adult · $30 child · Kids 5 & under free
"Tours are relaxed, entertaining, enlightening, and highly recommended for anyone seeking a bigger, more flavorful slice of Santa Cruz history."
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? View All Tours & Availability
Pick a date, then choose from available tours and times.
Adult (18+): $45 · Child (6-17): $30 · Kids 5 and under are FREE with adult ticket
Full refund if cancelled 24+ hours before tour start time
Tour Details
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 within the timeframe listed 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 Team OffsiteWant the Full Experience, Your Way?
Private tours for families, couples, and groups. Your schedule, your pace, your interests. Starting from $250 for up to 6 guests.
Explore Private ToursGuests Love Our Tours!
"What an informative and interesting perspective of Santa Cruz! Matt was very personable and it was a lovely walk from the Boardwalk to downtown. As a local, I thought I knew the history of the area, but turns out there is more to learn! Fun tour!"
"This tour was a fun way to learn about SC while also moving and connecting. Definitely recommend!"
"My wife, baby, and I had such a great time on this tour with Matthew! We've lived here for 5 years and learned so much about the history of the town. We could ask Matthew anything and he always had an informed answer. It was also the perfect morning walk/workout!"
"Great knowledge of his hometown history. Enjoyed learning about Santa Cruz from someone very familiar with it. Great downtown and mission choice of route."
Reviewed on Google · Airbnb · TripAdvisor · Viator
⭐⭐⭐⭐⭐ 12+ five-star reviews
Questions? Call or text us at 831-275-2566