[J.A.Sucker]

Go to Testarossa for wine tasting in Los Gatos (about 15 minutes from SJ). Los Gatos is a very nice little town - have a lunch at a place called the Wine Cellar - very good food, excellent by the glass wine list, and very mellow. I like hanging out down there.

Downtown Palo Alto - University Ave (20 minutes north) is a really nice town, as Zee said. Lots of great restaurants there - I like Osteria (home-cooked Italian), Evvia's (Greek), La Strada (Northern Italian). There's several nice cafes to just hang out and and relax. On California Ave there is a great resaturant/bar called La Bodeguita Del Medio. Cuban joint - great rums (get the Zacapa 23 year), outstanding wine list, great beer on tap (Chimay!). You can have a cigar and relax (either inside or out). Restaurant there is a must-do as well.

There's some great Asian food of all kinds around SJ, of course, but specific likes would be needed.

I also agree with Zee's suggestions about Santa Cruz, et al. I also like going to Capitola (next to Santa Cruz) to sit on the beach and have cocktails at Zelda's. There's also some good food to be had on the pier at Santa Cruz (I forget the name of this Italian/seafood place, which is a shame because it's excellent).