Find your way to the historic Castro Theater in San Francisco's Castro district for your moderate 5-mile (8-km) urban hike. Be sure to wear proper hiking shoes to tackle the city's famous hills and bring some drinking water.
Start with a trek up to the top of Kite Hill, a green space that's easy to see but hard to find and is popular with the neighborhood residents. After pausing at the top of the hill for great views and some photo ops, continue to the Seward Street Slides, a hidden gem that has brought delight to kids and adults alike over the years. Make like a local: grab a piece of cardboard and let 'er rip down the curved, cement slides, clearly built in an era before playground safety was a concern.
Walk through a hidden eucalyptus forest behind Sutro Tower, one of the city's unmistakable landmarks. Follow your guide to an unmarked hiking trail, less of an official trail and more of a path worn by residents over the years, to the summit of Twin Peaks. Catch your breath and some truly magnificent views of the San Francisco waterfront and the East Bay Hills beyond.
Conquer Tank Hill next, another popular neighborhood park for views and dog walking. This 650-foot (198-km) high summit gives views of the northern side of the city, the Golden Gate Bridge and Golden Gate Park.
Descend via the 211-step Pemberton Place Stairway, winding through the beautiful neighborhood houses and private gardens. Return to the Castro Theater to end your 3-hour tour, having seen a part of San Francisco that many travelers never witness.
