We have been doing some more thinking since I posted this and are looking at Los Gatos now. Your favorites there?
Thanks so much.
Los Gatos has some very expensive, supposedly really good restaurants like Manresa, Dio Deka, Forbes Mill and other places like Los Gatos Brewing Co but I can't speak as to how they'd work for a reservation for 10. Parking could be all over the place.
In my opinion, nothing beats Paolo's in San Jose for a special occasion. It's my go-to spot. Very nice decor, top notch (not snooty) service, and the food is positively sublime (high end Italian, grilled meats, etc). Parking is a breeze, they take reservations, and can accomodate a party your size. Check it out at http://paolos.com/ It is more upscale than either Maggiano's (loud and crowded) or Il Fornaio (personally I do not care for the food at the Il Fornaio in San Jose, although the one in Palo Alto is good.)
The only catch might be if there is a performance at the CPA next door night you want to go. Then it is very crowded, but all the chaos subsides by 7:45 pm.
Oh, and I left out 71 St. Peter at 71 San Pedro Square in downtown San Jose. Nice atmosphere and the food is very good quality. Pastas and grilled items, etc. They have a private room that would be great for a party your size. There is a large parking structure across the street.
As for Los Gatos, most of the nicer places are VERY expensive, more so than even Paolo's, or aren't good for groups. The food at Los Gatos Brewing Company is excellent and they can definitely handle 10, but it's usually crowded and loud. Lots of kids. You know, brew pub (although upscale). Parking is usually not a problem in the evenings as there is a bank pretty close and you can park in that area. Forbes Mill Steak House could also take 10, I found it okay but nothing too great although it gets good reviews on Yelp. Parking may be a bit more tricky there but probably do-able.
Good luck and let us know what you pick!
I thought I should report back on this thread since I have now posted another different question about Saturday lunch the next day. We decided to book a group reservation at Campo di Bocce in Los Gatos on the recommendation of a friend. We will do a family style Italian dinner followed by 1.5 hrs of bocce ball. It sounds like lots of fun for our group of about 13.
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