Northern California. That’s where we are.
I don’t have to tell you why you love San Francisco. It’s a cheap and easy CalTrain run up to San Francisco from Downtown San Jose, and that’s the best way to get there. San Francisco’s steep hills make driving interesting, particularly if you’ve got a manual transmission. But driving isn’t the problem, parking is the problem. Take the train, and then cab or MUNI around the city.
If you’re planning to use mass transit to get around, check out the Bay Area Clipper Card. Much like London’s Oyster card, Dublin’s Leap card and the Carte Orange of Paris, Clipper is a contactless transit payment card that makes navigating the different transit agencies and services a breeze.
People think “Napa” but Santa Clara County, Santa Cruz Mountains and Livermore are all closer, cheaper, and top-notch. I’m not telling you not to go to Napa, but you can save yourself a few hours of travel if you take a chance on more local wine regions.
The Pacific is pretty cold up here, but you can get some good surfing in around Santa Cruz, and it’s less than an hour drive (unless traffic over the hill is bad).