A Weekend in Val d'Orcia, Tuscany, Italy


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Ready to dive deep into Tuscany in just one short weekend!? I have your itinerary HERE! This is the short version. You can click on the any of the links for a full write up and photos of each town.

Friday - stay just outside of Siena! We stayed south in Monteroni d'Arbia. Spend a little time exploring the area and/or a couple hours in Siena. In Monteroni check out the village, the Grancia di Cuna nearby, the water mill, and all the churches. The town is super cute and there's a huge park to play in! Or take a hike on the Via Francigena! Have dinner at La Valcerena.
Read Part 1 -Monteroni- in its entirety here!

Saturday - set out early south on SR2. Stop at Buonconvento, "happy lucky place". You won't regret it! Have a coffee and explore the town.
Read Part 2 -Buonconvento- in its entirety here!
Back on SR2, you can either follow the signs to Montalcino to the right or forward march to Torrenieri - it's a cute village worth the drive through. From there, follow the signs to SP14 to Montalcino!

We parked at the bottom and walked up. There is more parking closer up, just don't go in the ZTL's!!! You'll pay a hefty fine. What to see: Fortress - pay the fee in the wine shop and go up. Beautiful views!! Tons of wine tastings throughout the city; just pick one! Don't skip the wine! Brunello and Rosso Montalcino are two of the most famous in Italy. Have lunch here too. We opted for a packed picnic near the Enoteca (at the bottom of the hill).
Read Part 3 -Montalcino- in its entirety here!

Get back on SP14 towards San Quirico d'Orcia. This is one of the most scenic stretches of road in all of Tuscany. Right before you arrive, after a long bridge, you will recognize a crop of cypress trees on the side of a hill. These are the most photographed trees in all of Tuscany. There is a pull off area and gravel drive that you can take a walk up for some photos. 

Explore San Quirico - the porta's, the churches, the Horti Leonini gardens - WOW!! 
Famously: the Collegiate of the Saints Quirico and Giulitta: check out all the sculptures and notice that each of the lions guarding the entrance are in different poses. The gardens offer more breathtaking views over the Val d'Orcia. You can even see the volcanic Monte Amiate. Don't skip the famous Porta Cappuccino either. 
You could also have lunch here if it was too early in Montalcino. Plenty of restaurants and cute bars w/gardens.
Read Part 4 -San Quirico- in its entirety here!

The drive from San Quirico to Pienza is even more spectacular. Rolling hills, lines of cypresses, and one of the most beautiful and photographed chapels in Tuscany, the Cappella of Vitaleta. 
I recommend setting and following your GPS to this one. If you stop at the first pull off (where you can see it to your right) it's a very far walk to the church. If you follow your GPS around, there is a parking area and a much shorter walk. Enjoy the enchanting surroundings. This stop is a must!! (keep in mind there is a walk on a gravel path - not wheelchair nor stroller friendly).

We barely touched the surface in Pienza. This town, born from a dream, is a bit busier and bigger than the previous. Still amazing! Still beautiful! But if you want to finish the day in Montepulciano, you have to hustle! #1 task: Pecorino cheese!! Do a tasting!
Read Part 5 -Pienza- in its entirety here!

A final drive to Montepulciano to catch the sunset and all the wine!!
We were quite rushed here and quite pooped. Maybe this little tour would be better spread over 2-3 days instead of 1. We like a good challenge though!
Read Part 6 -Montepulciano- in its entirety here!

Wear comfy shoes for Montepulciano because it is a super UP and DOWN town!! Lots of shop and stores to explore, so bring a deep wallet too ;) We bought a new olive oil ceramic and plenty of wine. The cheese and meats are fantastic too!

We made the drive back to Monteroni for a quick pizza and slept like logs!

Sunday - pack it up and head to Siena!!