Wind your way through the historic heart of San Francisco, tracing the “ghost” of the original 1849 waterline and the chaotic birth of a global metropolis. Starting where the bay once met the shore at the Transamerica Redwood Park, this tour takes trekkers through the preserved brick alleys of Jackson Square, the lawless echoes of the Barbary Coast, and the cultural crossroads of Portsmouth Square and North Beach.

We’ll stop at several famous points of interest and hidden markers, including the site of the First U.S. Mint, Old St. Mary’s Cathedral, Portsmouth Square, and Hotaling Place. You’ll learn about the legendary figures who defined early SF—from the eccentric Emperor Norton and his faithful dogs to the “Demon in the Belfry” and the rebellious Beatniks of Columbus Avenue. Along the way, we’ll point out the best secret photo ops, like the perfectly framed “urban canyon” view of the Transamerica Pyramid.