We continue our tour of our favorite corner of Tuscany in Pienza. Such a great little town and a welcome bit of flat ground. There are beautiful side streets and incredible views of the Val d’Orcia just behind the Duomo di Pienza. As we’ve said before, we love Montepulciano and think it’s a great home base. So if that is where you’re staying, Pienza is a super easy day trip or part of day, if you have some other experiences you want to fit in. Here’s our plan for some must sees in town.
Getting there and around town –
If you’re coming from Montepulciano, Pienza is just about 25 minutes. Close enough to even get a taxi for the day if you’re not in the mood to drive yourself.

- If you drive, parking will be slightly easier than Montepulciano, but that does not mean easy or abundant. As with all the town in the area, you must park outside the history center and expect to pay.
- The great thing about Pienza is it’s flat! In the history center, you have barely an incline. This makes it much easier to get around for those with mobility issues and a nice break if you’ve been going up and down in the days leading up to it. It’s also small enough that there isn’t really a need for the little bus tour you’ll find in Montepulciano. Making it overall a very approachable town.
What to see –
- One of the main things to see is the town itself. Yes, many Tuscan hilltop towns are beautiful. They take you back in time in almost a “do people actually live here” sort of way, but Pienza is another level. Aeneas Silvius Piccolomini, who would become Pope Pius II, was born in Pienza. After he became Pope he had the entire village rebuilt as an ideal Renaissance town to serve as his retreat from Rome. So a bit more planning and thought went into it than most towns.
- Palazzo Piccolomini (Corso il Rossellino, just off Piazza Pio II) – This was the summer retreat of Pope Pius II. They offer guided tours every 30 minutes and that is the only way you can see inside the Palazzo. However, it is free to visit the garden and take in the beautiful views of the Val d’Orcia. As well the courtyard just inside the entrance. If you’re a fan of the Medici series, you will recognize it as the courtyard to the Medici home, Palazzo Riccardi.
- Duomo di Pienza (Corso il Rossellino, in Piazza Pio II) – Just next door to the Pope’s home, the Renaissance façade leads into a late interior, not as ornate as many cathedrals in Itay, but still beautiful in its own way. It is also interesting to notice as you walk to the altar you can feel the floor slope. That’s because it is ever so slowly sinking. It was built on a sandstone base, so as you walk you will see cracks in the ground and the walls.



Where to eat –
- Breakfast – Today breakfast at your hotel probably makes the most sense. It’s possible to see much of Pienza on a day you choose to relax in the morning or maybe even make another stop before getting into town.
- Lunch – Case Nuove (Via delle Case Nuove 7, just across from our favorite gelato place) A great little casual restaurant just off a quiet side street. Prices are reasonable and the service is very friendly. Classic Tuscan dishes with plenty of wine options. If there is space, sit outside and enjoy the world going by in this little corner of Pienza.
- Dinner – La Bandita Townhouse Caffe (Corso il Rossellino 111) This restaurant is part of small hotel, with the entrance just off Via Sant’Andrea. As it is owned by a former MTV exec, the food is going to be a little more varied than other options. Of course you will find classics based on the season, but they also have a great burger if someone is craving something other than pasta. It’s small and can fill up quickly, so make reservations if you want to be sure to get a table.
- Gelato – Buon Gusto Gelateria (Via delle case nuove 26) Yes! The great gelato shop from Montepulciano has a location in Pienza. Nicola, has the same commitment to natural and seasonal flavors at this location. Even if you had it in Montepulciano, have it again here.



Where to shop –
There is some great shopping in Pienza. One difference from Montepulciano is the number of food shops available. So many good options for cheeses and other delicious items to talk home. Here are a few we make sure to stop in each time we visit.
- Ceramichr D’Arte Silvia Barbieri (Piazza Martiri della Liberta 5\6) – beautiful handmade Italian ceramics, some different styles than other stores
- Altroier (Corso il Rossellino 8) – classic Italian linens
- Marusco e Maria (Corso Rossellino 21) – wide range of foods from the Val d’Orcia area
- Casini (Corso il Rossellino, 101) – clothes & accessories
- Bottega Del Naturista (Corso Rossellino 16) – Cheeses exclusively from Il Caseificio Di Mario – a small family run dairy & cheesemakers in Pienza



Do you have more than one day planned for Pienza or maybe want to add an activity to your time in the area? Here’s one of our favorites, very close to town.
- If you’re looking to get the Tuscan farm experience or maybe to better understand the cheesemaking process, Podere Il Casale is a great stop. They’re an organic farm, raising their own livestock for the milk to make cheese. They have vineyards and produce their own wine. As well as olive trees to produce their own olive oil. They really cover it all. They have many activities available. Farm tours, wine & cheese tastings, cheese making demonstrations, or you can just go for lunch. (About 15 minutes from town, Via Podere il Casale 64)

Pienza is a small, but beautiful town. Even if it’s just an afternoon, it’s worth making the trip to take in it’s charm, look at the amazing panoramic views of the Val d’Orica, and of course, try all the local treats.