ISO Small must see towns in Tuscany.

We are spending two weeks in June/July of 2023. We are staying near Orvieto and plan to day trip around. I’m not afraid of driving two- three hours to get to the best place. We love small mom&pop shops as far as food goes we just love the best food. We want to eat where the locals love to eat. We don’t really want the touristsy places we will do the obligatory visit to Rome and Florence, but we want to find the magic of the small hill and fort towns in Tuscany. We want to visit vineyards and wineries with the best wine not necessarily the most popular by name. We love to explore and are up for most things. Please pour out your favorite experiences, places, and activities that we should consider. I’m traveling with 9 other people all in there 50-70s.
That sounds like a lovely plan for the whole group. If you’re staying in Orvieto I imagine you’ll also add in places in Umbria but since I don’t know many beyond the most well-known (Orvieto, Perugia, Norcia, Assisi), I’ll stick to ones in Tuscany.

Keep in mind that June and July are busy season but in any case smaller towns and villages will remain ideal with smaller crowds.

I particularly love the Valdorcia and southern Tuscany so recommend you consider Montepulciano and Pienza, Cortona and Arezzo, San Quirico d’Orcia and Montalcino. If you want to try thermal baths, you can go to Saturnia or Bagno Vignoni although Saturnia is more scenic (also very crowded).

If you do head toward Maremma, I would suggest going to Pitigliano, Sorano, Sovana. The Tarot garden in Maremma is unique - read more about it here:

Then you can spend an entire day exploring the small towns in Chianti such as Castellina in Chianti and Radda and Panzano and Greve, as well as Gaiole. If you look through our website, you’ll find all the links to recommendations at each of these places. We have articles on most of all these places I’ve suggested.

Although Pisa gets busy, the climb up the leaning tower is incredible, one I do recommend doing at least once in a lifetime.

Lucca is another lovely town, not super small but never feeling too crowded. Siena is not on your list but I also highly recommend it. To avoid on July 2 when the Palio is planned but lovely even with crowds. Visit inside the city hall (palazzo civico) is highly recommended!

I think once you make a list, you’ll have to go back and select because even two weeks will not be enough.