OK, I'll take this one... I live in San Jose so here are the places I go on a somewhat frequent basis:
1. West Coast Cigars - 1650 Almaden Road, San Jose -
www.westcoastcigars.net I really like this place. Probably has the best prices of any B&M in the area with a large selection. The people are friendly and you can bring your own drinks to enjoy with your cigar. It is a blue collar crowd for the most part and the place actually looks a bit like a frat house, but this is the environment I prefer over a more pretentious crowd. There is a small lounge area inside with a big screen tv and large comfy leather chairs and couches (kind of like a living room, but with more seating than walking space). The outdoor area is very large and has a bunch of patio furniture to use also. The special events/guests that they bring here are top notch also so check their website before you come to see if you can make any of them. Next week is Don Pepin and a few weeks ago was Eddie Ortega.
2. Mission Pipe and Cigars - 1205 The Alameda #20, San Jose -
www.missionpipe.com This place is really good too, but a little pricier and a little more exclusive group of patrons. They also have a huge selection of good smokes. The indoor lounge is fairly small and you might get strange looks as an outsider if you choose to sit down in there. When I'm here, I tend to move to the small outdoor area at the back of the store.
3. If you are looking for places to bring your own cigars, I would recommend the Hedley Club Lounge in the Hotel De Anza in Downtown. They have an outdoor area that is covered with heaters where you can sit down and puff away on a good cigar that you brought yourself.
www.hoteldeanza.com/hedley_club.asp 4. Finally, if you want a little more pub type atmosphere, the Downtown Britannia Arms is a good place to go. They also have a large covered outdoor area with heat lamps. More informal than the hedley club, but still cigar friendly.
Hope this helps. Let me know if you want to herf with a couple of CG's while you're in the area.