Been to Tuscany quite few times, stayed in Florence and the countryside, back of beyond and little villages.
My other half is incredibly allergic to insect bites but as long as you're careful it's not too bad. We have ludicrously strong repellent, candles and joss stick things impregnated with citronella. If the worst does happen then pharmacies carry industrial strength antihistamine creams that can be bought over the counter.
My favourite place is Panzano In Chianti, we're just about to book an apartment that's part of a castle, we'll hire a car from Pisa airport. Driving isn't a problem if you're reasonably proficient.
Pretty much every town or village has excellent places to eat from Michelin starred to little enotecas. There's a fantastic wine shop in Greve which if you're in the area I can't recommend highly enough, you get a credit card that you load with Euros and then you pop that in a dispenser that gives you wine by the glass, so you can try before you buy.
If you speak even the worst Italian and show an interest, the Italians will love you and go out of the way to befriend you, I've drunk fantastic wines with enoteca owners and their friends after just a couple of visits to their shop.
