This three-hour urban hiking adventure starts off at Levi’s Plaza Park, where your guide will be waiting (be sure you’re sporting your most comfortable shoes). Once there, get immediately into your workout with a heart-pumping climb up the Filbert Street steps along Telegraph Hill. The steps are separated into three sections, providing great excuses to stop, take in the incredible panoramic views and snap a few picks. Along the way, keep your eyes and ears open for the wild parrots of Telegraph Hill. You’ll usually hear these beloved birds before you see them.
Atop Telegraph Hill is the 210-foot-tall Coit Tower, an art deco monument and one of San Francisco’s most iconic landmarks. Climb to the top, savoring unprecedented views of the city itself, the Golden Gate and Bay bridges and Alcatraz Island.
Next, ascend a hidden staircase to Jack Early Park—a tiny lookout offering superb views of Alcatraz and Pier 39—before heading toward San Francisco’s Russian Hill neighborhood. Getting here requires a steep walk up Lombard Street, one of the city’s best known streets due to its unusual crooked section.
As you hike, climb and take in the views, your tour guide will share bits of local history and take you past some fun pop culture landmarks such as Macondray Lane, author Armistead Maupin’s inspiration for Barbary Lane in his Tales of the City novels.
Lastly it’s off to North Beach, San Francisco’s lively Italian neighborhood. Explore its alleyways and learn about its interesting past before returning to your starting point via a stroll down the Greenwich Street Stairs.