For my first wine tasting experience, my friends and I visited
Costello di Amorosa in Napa Valley. It's a large, Tuscan-style castle with animals roaming in the front lawn. We did the basic general admission, where we can freely roam the halls and sample 5 different wines. Despite my unfamiliarity of wine, I actually enjoyed each one I tasted.
The placement of the castle really makes it seem like we're in a different country... while just a half-hour South, is downtown Napa.