The first sizable coastal town south of San Francisco, Half Moon Bay (pop. 11,324) is 28 miles from the city but seems much more distant. A quiet farming community that’s slowly but surely changing into a Silicon Valley exurb, Half Moon Bay still has an all-American Main Street lined by hardware stores, cafés, bakeries, and the inevitable art galleries and B&Bs. The main event hereabouts is the annual Art & Pumpkin Festival, held mid-October, which celebrates the coming of Halloween with a competition to determine the world’s largest pumpkin—winning gourds weigh more than 1,500 pounds!

Until the construction of the $550-a-night beachfront Ritz-Carlton golf resort, the coastline of Half Moon Bay was almost completely undeveloped, but it’s still pretty nice and accessible, with a four-mile-long string of state park beaches at the foot of bluff-top vegetable farms and horse ranches. The town also retains its rural feel. But thanks to the presence of so many Silicon Valley billionaires just over the hills, it has significantly better restaurants. The best fish tacos (and great fish ’n’ chips) can be had at the Flying Fish Bar & Grill (211 San Mateo Rd., 650/712-1125), off Hwy-92 at the north end of Main Street. Excellent and not outrageously expensive Italian specialties are on the menu at Pasta Moon (315 Main St., 650/726-5125).

Map of Pacific Coast through San Francisco.
Map of Pacific Coast through San Francisco.