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I left off with my family and I driving south from Tuscany towards Pienza. Our route was scenic and not direct on purpose. You can take the highways to get places faster but why do so when half the enjoyment in this part of Italy are the drives?

If you haven’t, read Part I of this trip report before continuing below. I thought this would be a two-part series, but I underestimated how much I have to say about Tuscany… so lucky you as there will be three installments instead of two. Today, Pienza and the surrounding area. Next time, Monte Argentario and bit on Naples.


34 miles southeast of Siena, Pienza is a UNESCO World Heritage Site perched atop the Val d’Orcia and sandwiched between Montalcino and Montepulciano, two names that sound familiar if you care about wine.

Pienza is tiny, and the old town, completely enclosed by medieval walls, is even tinier. The old town smells distinctly of Pecorino, available everywhere as the ancient town is where the sheep’s milk cheese hails from. The real clincher, in my opinion, is the view from the south-facing wall. We landed an Airbnb right on it. That link will take you to its listing.

Truth be told, the apartment was a little tight for four adults (see pics on listing). We’re pretty laid back so we managed, but I think it’s better suited for a couple or a family with one or two small kids max. And if you’re particularly tall, forget about it. This apartment was built when people were shorter. We all hit our heads on beams repeatedly.

Aside from that, it was a charming apartment with a spectacular location that provided an unforgettable view of the Val d’Orcia. The host was responsive, solving the internet problem the same day it happened (or didn’t happen, I should say) by purchasing a 4g portable router.

The airbnb was along this wall.
The airbnb was along this wall.

The Stand Out Eating 

The eating in Pienza was unparalleled.

I ate at Sette de Vino three times during a short stay. It’s best for lunch, but good any time of day. The menu is small, everything on it you will want to order twice. The owner is a character, a longstanding character in the town we found out, the more locals we spoke to. He grew up in restaurant. Let him order for you and be entertained by him.

Just make sure the bean soup is in your order. It’s unique to the area and a delicious departure from all the pastas you’ll eat, loaded with veggies, beans, and flavor.

La Bandita Townhouse is good for a splurge. Everything from my memory was top-notch; mostly modern twists on classic Italian flavors. The setting, wine list, and service–on top of the food–were all impressive. There are so many delicious mom-and-pop places in Italy that you don’t need to spend money on fancy places to eat well, but if you’re into gourmet dining experiences, give this place a shot. I didn’t feel my money was wasted. The hotel it’s attached to also looks like a lovely option for accommodation in Pienza.

All the plates were works of art, in presentation and taste.

Thought I'd get tired of the strong flavor of truffle in Tuscany where it's ubiquitous. Surprise...I DIDN'T. 
Thought I’d get tired of the strong flavor of truffle in Tuscany, where it’s ubiquitous. Surprise…I DIDN’T.
I have multiple clothing items that exact tone of mustard.
I have multiple clothing items that exact tone of mustard. You?

Walk 20 minutes down the hill south of Pienza and you’ll pass an unassuming mom-and-pop joint–or in this case, daugher-and-pop joint–adjoined to a b&b called Poderuccio. We enjoyed delicious home made pasta here and a truffle fondue.

The owner was also a character (noticing a trend?) and just as friendly as could be. We enjoyed wading our way through an Italian/Spanish hybrid conversation amidst a power outage during dessert. He parked himself, all the bottles of Sambuca he had at his disposal, and a camping lantern at our table and we made one of our favorite memories of the trip in his cozy restaurant that in the span of a couple hours become to feel more like our living room. Bella Italia. You know you were absorbed in the atmosphere when there are no photos to speak of.

We ate a few breakfasts at a little cafe with good crepes and coffee Caffe Della Volpe

Caffe Della Volpe
Caffe Della Volpe

Across the walkway from Cafee Della Volpe was competition for my favorite gelato of the trip, Buon Gusto Gelateria. They have classic flavors like Pistacchio, but also modern ones like lavender.

The Other Fun

e-biking around the Val d'Orcia
e-biking around the Val d’Orcia

One day Withers (the boyfriend) and I rented e-bikes from E-Bike Tuscany. This was my first experience with e-bikes. What an incredible invention! You can cover so much more ground, including the hilly terrain of Tuscany, and carry on for so much longer than your own standard stamina could allow. And what a gorgeous place Tuscany is for bike riding. The speed you have to maintain driving roads means you miss a lot of the scenery, but on a bike you get the chance to soak it all in. If you’re a beast, good for you. You can bike Tuscany. If you’re a normal person, rent an e-bike. And use E-Bike Tuscany, her bikes are very high quality! Not to mention the owner will, once again, entertain you with her strong personality and sense of humor. I wish all the Italians I met on this trip were my aunts, uncles, cousins, and nonas.

Give me more pecorino! A scene from the e-bike ride.
Give me more pecorino! A scene from the e-bike ride.

Nostra Vita Winery 

Nostra Vita means our life in Italian, which is the perfect name for this family-run vineyard. We stumbled across this place by accident, mainly because we had made no reservation for a tasting anywhere and this place accommodated our last minute nature.

The grounds were breathtaking, the tour guide proud and friendly, and the Brunello wines was very good.  They make art along with wine, and showed us the mobile artist studio on wheels that physically separated into four pieces, in case the artist decided to let in some natural light.

Sculptures dotted the property, like the one you can see in the background of the photo below, situated amongst an herb garden. I was ready to move in.

Enjoying ourselves at Nostra Vita
Enjoying ourselves at Nostra Vita

Bagno Vignoni and the Other Hot Springs

A half hour drive south of Pienza are the natural hot springs of Bagno Vignoni, pictured below. While I enjoyed Bagno Vignoni, in retrospect I think we should have continued south on the same road to come to Bagni San Fillipo. Those springs, from photos at least, appear to be a little less crowded.

Surrounding Towns

Don’t forget you’ve got Montepulciano to the east and Montalcino to the west, two picturesque medieval hilltop towns worth a visit if you’re in the area. I didn’t make time myself as I was working on this trip, but below are some pictures from my parents day trips.


Part III coming soon…

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