Iconic Highway 1 does not end in San Francisco, though most travelers only make it that far. Beyond the Golden Gate Bridge the road gets decidedly more lonesome, winding through rocky headlands and ancient redwood forests—the old stomping grounds of John Muir. In a place where a still-wild West meets a wilder Pacific, strange things emerge from the coastal fog, like tule elk on Point Reyes, or Boonville, a town with its own language, called Boontling. San Franciscan Brad Day, a 21st-century Muir, was so taken with the wilderness north of his home that he quit his job in sales two years ago to explore the region full-time, sharing his favorite trips on www.weekendsherpa.com. "In March the wild poppies start to bloom," says Day, 29. "That should be reason enough to visit." Muir would agree: "The attractions of California were yet stronger than all others," he once wrote, describing the place as "the floweriest part of the continent."
Day 1
Surf in Bolinas—with south-facing beaches and calm waters, it's the best place in NorCal to learn. Hike Point Reyes National Seashore's remote Tomales Point Trail, a 9.5-mile (15-kilometer) traverse leading to expansive ocean views. At nightfall, bunk in a cozy cottage with a private garden.
Day 2
Kayak Tomales Bay to spot seals and otters, then pluck and shuck oysters from its sands. Go north and hit a long, spectacular stretch of Highway 1. Stop for grub at the Highpockety Ox in Boonville; bonus points if you order in the local lingo (try: "It's bahl hornin'"—"good drinking"). Sleep in Upper Lake at the Tallman Hotel.
Day 3
Grab a free map at the trailheads of Boggs Mountain; BYO bike for 15 miles (24 kilometers) of singletrack, zigzagging through ponderosa pines. Afterward head to Buster's in Calistoga for the best BBQ west of the Mississippi. Then sip the Zin in St. Helena and watch the hills turn gold in Napa Valley.
Day 4
On a clear day atop Mount Tamalpais you can see as far as the snowcapped Sierra Nevada. Fly off the peak with instructor Paris Williams, a four-time U.S. National Hang Gliding champ. Come eve, hike in to Mill Valley's West Point Inn.
THE VITALS
Do: Bolinas Surf Lessons ($50; www.surfbolinas.com); Point Reyes National Seashore (free; nps.gov/pore); Blue Waters Kayak ($88 for a four-hour tour; www.bwkayak.com); Hog Island Oyster Company for shucking, then eating ($8; www.hogislandoysters.com); Highpockety Ox restaurant (www.highpocketyox.com); Buster's Southern Barbeque (www.busterssouthernbbq.com); California Hang Gliding ($325; www.californiahg.com)
Sleep: Point Reyes Station Jasmine Cottage ($220; www.oldpointreyesschoolhouse.com); Tallman Hotel ($149; tallmanhotel.com); West Point Inn ($35; westpointinn.com)
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