We just got home a week ago from 5 weeks in Italy, first trip since both being retired. One stay, which we’d like to do a second time, was near Castegneto Carducci, just inland from the Etruscan Coast, in southwestern Tuscany. We flew in and out of Rome this trip, but for a return, are thinking of flying into Pisa, then heading south along the coast. It’s Super Tuscan wine country, with some charming but less-visited hill towns, and sandy beach access, all nearby. Non-Italians seemed to be mostly Germans this fall, very few other Americans, and maybe it’ll be busier in the future, but certainly not like Florence, Siena, or Rome. We stayed in one of the 2 apartments above the owner’s country house. They have an enormous garden and a rural setting, although theirs is not technically called an agriturismo, but there are agriturismos in the area. They offer cooking classes, bike riding (big cyclist area), and we even helped them pick their olives for the year one day, and got extra-extra virgin oil as thanks.
Another week, we stayed at a remote agriturismo in southern Umbria, close to Spoleto, west of Orvieto.
IF you started on the west coast, north of Rome, you could head further south to the Amalfi coast (we stayed in Sorrento on a previous trip, for access to Amalfi, plus Pompeii, Herculaneum, Naples, Capri), then up north for Lake Country. Maybe fly home from Venice, if not Milan?