Walking across the Golden Gate Bridge with a backpack full of snacks feels strange only until you reach the Coastal Trail, the entrance to the Golden Gate National Recreation Area. A metropolitan backcountry that contains more than 200 miles of trails, GGNRA stretches along the Marin Headlands from the bridge to Point Reyes. Ascend the Coastal Trail to the ridge above Gerbode Valley and walk north on the SCA trail for nine miles along windswept, rock-studded hills. By late afternoon, you'll reconnect with the Coastal Trail, which runs along the bluffs between Tennessee Valley and Muir Beach. Stumble into Muir Beach's Pelican Inn and ask for Room 7, the only one with a king-size bed ($190; pelicaninn.com).
The flat walk for the first two miles from Muir Beach on the Redwood Creek Trail is forgiving. Then it isn't, as you ascend from the Frank Valley to a clearing with a broad view of the bay. Take the Dipsea Trail for five miles until you reach Stinson Beach. The trail ends 100 yards from the Live Water Surf Shop (rentals, $20; livewatersurfshop.com). Stay at the Sandpiper Inn (from $95; sandpiperstinsonbeach.com), and eat at the Sand Dollar Restaurant. The local barbecued oysters are worth the wait (stinsonbeachrestaurant.com).
Two blocks outside of town, the Matt Davis Trail quickly rises in a lush forest. After 1,000 vertical feet, the path levels and traverses the flanks of Mount Tamalpais. The Matt Davis continues toward U.S. 101, passing the Pantoll ranger station. Stop at the Mountain Home Inn (mtnhomeinn.com), which sits on a ridge dividing Mount Tamalpais State Park from the metropolitan area, and celebrate the homestretch with a Niman Ranch burger. Then follow the Tenderfoot Trail as it plunges into Mill Valley, where buses leave for San Francisco (goldengatetransit.org).