If you like edgy, windswept, impossibly romantic vistas, here’s your wild card: you and yours tramping along Wilbur's Watch Trail in search of the lone bench at the end of the continent. The coastal drive down Highway 1 provides an engine-revving preview. Near Pigeon Point Light Station, park and hike the one-mile (one-way) trail, thanking the Peninsula Open Space Trust for saving these pristine hills from hotel development. When you reach that sweet seat at the end, break out the Cab, cheese, and chocolate and have a feast. Devour the scenery too: those whales are spouting just for you.
To reach Wilbur’s Watch, head south on Hwy. 1 to Pescadero, then six miles past Pescadero Rd., turn left onto the southern of the two Pigeon Point Rd. exits (not the first one leading to the lighthouse). The parking lot and trailhead are immediately on the right.
TIP: Speaking of Cabernet, pick up a bottle and some dark chocolate at the San Gregorio General Store, a nearby grocery located on the corner of Highway 84 and Stage Road. It's an eccentric, lively spot where you can purchase anything from raccoon traps to 18 flavors of tequila. It features live music—Irish R&B, anyone?—on the weekends and is guaranteed to send you off with a smile.
San Gregorio General Store, Highway 84 and Stage Road, San Gregorio; 650-726-0565.