I'd definitely look at a self-guided multi-night bike tour, if time permits. Wife and I did one with https://cicloposse.com/ through Pienza, Montalcino, Montepulciano ending in Sienna, in 2013 and it's easily my favourite memory from our two weeks in italy. We'd booked with a more SEO-optimized, english speaking firm but they were just re-selling cicloposse services.
We ate at amazing restaurants, and really experienced the country in a way I've struggled to replicate in most other travel. Strong recommend.