@zolaris nice choice! Tuscany is beautiful. The most visited cities (like Firenze, Pisa, Siena, etc.) are beautiful but may be crowded and a bit expensive. The small towns and the countryside are usually more accessible and you can find some "real" trattorias.
I'm not that expert, anyway, so I'm boosting your messages so maybe someone from #Toscana will be able to give more hints