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Where to stay:
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About the area:
San Francisco is about 50 miles north of San Jose. Cupertino is about 5 miles north of San Jose. The beach is about a 40-minute drive "over the hill" to Santa Cruz from San Jose on Highway 17. Public transportation can be hit and miss. Your best bets are CalTrain if you're staying in the South Bay and want to spend a day in San Francisco.

Things you may want to see:
In the South Bay:
The Tech Museum
The restaurant where we had our first date.
Willow Glen
Los Gatos
Stanford University

San Francisco:
Golden Gate Bridge
The Presido
Golden Gate Park
Chinatown and North Beach
Alcatraz and Fisherman's Wharf.
A Giants game in Pac Bell Park

Wine Country:
Napa and the wine country are about an hour north of San Francisco.

Santa Cruz:
The Boardwalk, the lighthouse, the surfers at Steamers.