290 Wine Shuttle was great for us! We just hopped off where we wanted and then when we decided to head somewhere else it was a short wait to hop back on and go to another winery.
We've also used them for a private van shuttle and it was less than stellar. The van was falling apart and about 1/2 of us got motion sick. Not sure if all of their private shuttles are like that but we all decided we would not be doing that again.
And we've also used Reserve Tours - they were great!
As far as wineries go, we really enjoyed Grape Creek for a bigger more grandiose winery(try their Serendipity, its one of the best wines I've had, we joined their club just because of this wine) and then Hilmy Cellars for a smaller, boutique type place. I love the property of Becker Vineyards and their wine is good, the Reserve Cabernet is one of my top favorite wines.
We also have been to William Chris and weren't super impressed, the wine was good but the servers and employees just spent all their time trying to force us to buy bottles when we just wanted to enjoy the scenery and wine.
Torre di Pietra was just ok, not a great place for a larger group, we all had to separate to do our tastings and the wine was just sub-par.
I have not been but have heard Narrow Path Winery & Four Point Cellars are really nice.
As far as restaurants, we usually go to Auslander -- they are really great about accommodating a large group and the food is good. Crosswoods is really good too, hard to get in with a large group but it can happen.