Hillsborough, CA

Hillsborough is an upscale residential enclave in San Mateo County, about 20 miles south of San Francisco via Highway 101 or the scenic Interstate 280. The town sits among rolling hills with a Mediterranean climate, connected by Route 92 to Half Moon Bay and easily accessed from SFO Airport 12 miles away. Notably, it's one of California's few cities that actually prohibits sidewalks to maintain its rural feel.