Surfers outside Cowell's Beach, Santa Cruz

Where Surfing Came to America

In 1885, Hawaiian princes rode waves here and changed the world. Walk the story with a local guide who knows it inside out.

★★★★★ 5.0 rating
Featured in Lookout Santa Cruz
Matt O'Leary, Walk Santa Cruz guide

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 Review
More About Matt →

Guests Love It

"Tours are relaxed, entertaining, enlightening, and highly recommended for anyone seeking a bigger, more flavorful slice of Santa Cruz history."
— Sophia  ·  March 2026  ·  Google Review

Reviewed on Google · Airbnb · TripAdvisor · Viator

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

MyTOQUE

Free 100 ml olive oil with $25 purchase

Moon Kissed

Moon Kissed

10% off

Within 3 Days

Mythic Games

Mythic Games

Free Magic: The Gathering welcome deck + 10% off

Super Silver

Super Silver

Free crystal gift with $10+ purchase

Within 7 Days

Hidden Peak Teahouse

Hidden Peak Teahouse

15% off

Artisans & Agency

Artisans & Agency

10% off

Nicely

Nicely

10% off, including existing sales

Mission Hill Coffee & Creamery

Mission Hill Coffee & Creamery

10% off

Do you own a Santa Cruz business interested in getting more foot traffic?

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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. No conference rooms. No trust falls. Just genuine exploration that teams actually talk about afterward.

Plan a Team Offsite

Want 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.

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Ready to Book? View All Tours & Availability

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

🎁 Gift Cards — the perfect Santa Cruz gift