There are many small, very good wineries that you will encounter driving the roads of Chianti Classico. Nearly everyone speaks a little English - enough to get by. It wouldn't hurt to learn a few words, though. Just look for a Venditta Diretta sign and drive on in. Keep in mind that nearly everything except restaurants are closed from Noon to 3 every day. The big wineries are fun, but it would be a shame to miss the charm of some of the small places. Buy most of your wine in the USA - good Italians are widely available. Do however bring back some cheese - no problem bringing back any firm to hard cheese. Some of these you cannot get at home. I wish I had brought back more Pecorino Di Pienze. Wonderful.