I missed this post while I was in Vegas ad JWIntosh told me about it. I dont drink but the central coast is one of our favorite places. We stay in Avila Beach and hit the wineries as the wife really loves the Pinots from that area.
I am going to give this a hard look anyway as it is close. The chef sounds awesome. Where is your winery?
As far as cigar dinners, I go all the time. $100 to $150 is usually the ticket for a premium meal and cigars so this is not out of whack.