First things first: don’t wear shorts. Yes, it’s California, but San Francisco is not Southern California, and does not have a shorts climate. The locals laugh at tourists, shivering in their shorts (even heathens from the East Bay, like me, laugh at the tourists in shorts). Your best bet is long pants and a short-sleeved shirt, with a lightweight jacket for when it gets cool (as it will at night).
Don’t eat at restaurants at Fisherman’s Wharf- they’re expensive and have mediocre food (at least the ones I’ve been to were like that). You’ll do much better in Chinatown or North Beach (the Italian neighborhood).
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3. What’s the best way to do wine country?
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Don’t do it on a weekend, if you can help it. That’s when it’s really busy.
I like Sonoma better than Napa. What I like to do is to go to downtown Sonoma. There are a lot of wineries within a short distance of the town square. But don’t try to park on the square- look for street parking a block or so away, it will be much easier to find.
If you’re planning to go back to SF that day, and you don’t have a designated driver, I’d recommend hitting only two or (max) three wineries.
If you do go to downtown Sonoma, be sure to go to the Basque Bakery. They have wonderful breads, and reasonably priced wines by the glass.
Probably my favorite wineries around Sonoma are Valley of the Moon and Ravenswood.
BART, Muni, and walking within the city. Don’t try to drive between two places in SF- you’ll have major trouble finding parking.
You’ll need to rent a car to go to the wine country, but you might consider renting a car only for that day (or for that day and the next, so you don’t have to worry if you get caught in traffic and can’t return the car by the time the car rental place closes). If you drive around the Bay Area, particularly on any of the bridges or through the Caldecott Tunnel, expect to get caught in traffic.