Duration: 4 hours

Every couple of blocks, San Francisco transitions from Shanghai to Rome, Hanoi to San Salvador. For many, the beating heart of San Francisco is the legacies that lie within the generations of people - artists and activists, inventors, and survivors. On this three-hour walking tour (paired with an hour-long cruise) journey through some of San Francisco's most distinct neighborhoods, including North Beach and Fisherman's Wharf then depart on an hour-long cruise getting up close and personal with her most iconic structure, the Golden Gate Bridge.

In the 1960s, Beat poets like Allen Ginsberg and Jack Kerouac mingled with little Italian grandmothers on the streets of North Beach. Follow along on a dive into the city’s artistic roots starting from Jack Kerouac Alley. Move up Columbus Avenue - the main strip through the predominantly Italian neighborhood where your guide will uncover the hidden gems lying just beneath the usual hotspots. Further north, climb two blocks to "The Crookedest Street in the World", before heading to the chocolate empire of Ghirardelli Square. Savor a piece of chocolate, then wander on down to Fisherman's Wharf. It may be one of the city’s busiest tourist areas, but your guide will show you how to navigate the popular area before heading to Pier 39 to meet the real stars of the city: San Francisco’s resident sea lions.

You’ll round out the afternoon with a cruise across the bay, taking in some of the city’s best sights from the water. Your boat sails past the waterfront neighborhood of the Marina District, onto the Presidio, and travels under the Golden Gate Bridge. A loop of Alcatraz Island is a welcome addition to the hour-long jaunt - the closest you can get without Alcatraz tickets. Afterward, you’ll return to Pier 39 where you can spend the evening exploring the area for yourself and musing over everything you learned on your tour.