Down the California coast sits this small, touristy town along the Bay. Although Monterey is a bit campy and untidy, its patronage is perfect for Busking. Many Califonians come here for a quick weekend getaway, which makes the town a nice little hot spot for busking-friendly crowds. The tips haven't always been huge for me here, but spending some time in the Monterey sun can be quite enjoyable.
My friend and I, both bicycle touring enthusiasts, took a trip from San Jose through Santa Cruz and around the Monterrey Bay- about 120 miles. If long-distance biking is not for you, you can always get there with a regional bus from San Jose or by Amtrak. When you do, go to the main walking/biking strip next to the aquarium and multiple restaurants. And as a bonus, there are no requirements for permits in Monterey, to my knowledge, so have at it!