Tuscany with older kids/teens -- help needed with five day itinerary with car

You might check into spending an afternoon in one of the hot springs in the region.

Hi! We are also staying at an agriuturismo in Val d'Orcia with my tweens (twins-- age 12) in June. We're doing a day trip Siena; definitely checking out Montalcino & Montepulciano. Also going to do hot springs, pasta making class, and a farm visit, deciding on a truffle hunt too.

Just north of Siena are the Chianti villages. Among them you can visit, Castellina, Radda,Panzano, Gaiole, Greve. They are charming and will give you a feel for a more rural Tuscany.

There are several beautiful old towns, villages, and abbeys south of Monteroni d'Arbia, mostly along SR2 and SP146, such as Buonconvento, San Quirico d'Orcia, Murlo, Montalcino, Abbazia di Sant'Antimo (Abbey of Sant'Antimo), Bagno Vignoni, Pienza, Monticchiello, and Santa Fiora.

If you're going north to Siena, check out Monteriggioni and Colle di Val d'Elsa.

Also going to do hot springs, pasta making class, and a farm visit, deciding on a truffle hunt too.

@WrenG --- those sound lovely! Do you mind sharing if there is a particular site you are booking your truffle hunt or pasta making class through?

This is what we're thinking of (roughly) for our five full days:

Day 1: Siena-- considering the Savor Siena Food and Wine Tour to start the day and would spend the rest of the day exploring on our own.

Day 2: Picking up college-age daughter from Siena train station as her study abroad program will have just ended in Florence. This will chop up our day and I'm guessing she'll want to deposit her stuff back at the agriturismo, so thinking of doing some close-by things, such as visiting the Abbey of Monte Oliveto Maggiore (only 20 some minutes from our lodging) then Montalcino (only 25 min away).

Day 3: Heart of Tuscany drive w/ Pienza, Bagno Vignoni, and Montepulciano

Day 4: Cooking class for the whole family at La Pietre Vive in Castelnuovo Berardenga. Will have a half day left after we cook and eat our lunch... Will a half day be enough to appreciate Chianti and if so, what are the top spots to visit?

Day 5: More Chianti villages? More other heart of tuscany sights? would day trip to Assisi be too far?

Truffles are hunted in the fall, so if someone is selling you a truffle "hunt "in June or July, they are going to be depositing those truffles in the forest shortly before your arrival.

so thinking of doing some close-by things, such as visiting the Abbey of Monte Oliveto Maggiore (only 20 some minutes from our lodging) then Montalcino (only 25 min away).

I highly recommend visiting the Abbey. Check on their evening Vespers and Compline celebrated with Gregorian chant.

We visited while in Tuscany in December 2015. We visited the Abbey in the afternoon, then had dinner at a nearby restaurant. Since it was off season, it had just a cook and one person to serve. She spoke no English and our Italian is practically non-existent. Still, we successfully ordered a wonderful meal!

We then returned to the Abbey for Vespers. We took a seat in a folding chair in the sanctuary. Immediately a monk came by and invited us to join them where they were seated. He also handed us the books from which the ceremony would be held. They were all in Latin! He encouraged us to join in the responses. Since we are Episcopalians and sometimes sing in Latin, we caught on fast. There was one other visitor, a lady from a nearby village.

It was a wonderful and very moving ceremony. We told our server at our agriturismo our plans that morning and he remarked how much he loved Gregorian chant and actually had some CDs. While visiting the Abbey, we picked up a CD from them to give Marco as a Christmas present. When we gave it to him at breakfast the next morning, he teared up and said "one moment". A few minutes later he came back with a small jar of honey produced at the winery where we were staying. It was our turn to tear up and exclaim "mille grazie!". It's experiences like this that we travel independently..