Italy Recap Part 2: Pienza {including stops in Montepulciano & Siena}

In case you missed my Rome recap, you can find it here: Rome. Today i want to share the second portion of our trip, which was spent in Pienza. Grab a coffee (or a glass of vino), and settle in- it’s a long, picture-filled recap!


On Monday, we packed up and headed out in this bad boy:


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Poor RM- he was the only one who felt comfortable enough to drive this beast on the windy roads of the Tuscany region (and he knew how to drive a standard!). It wasn’t the most ideal vehicle to have due to the size of it vs. the size of the roads, but we made it work! He handled it very well, too, so that helped.

Anyway, before this trip I thought Tuscany was a specific place to visit like Rome or Florence, but in fact it’s a region to visit and you go there to visit all the little towns within the region. We absolutely loved Pienza as it had a super cute city center and was relatively close to other charming/picturesque towns. It was about 2.5 hours from Rome.


We stayed at Tenuta Santo Pietro, which was about 6KM from the city center, for our 4 night Pienza part of the trip. I loved the B&B for so many reasons! Here’s a bit about it from their site:

Nestled in the heart of the rolling Tuscan countryside, Tenuta Santo Pietro
is a tranquil oasis comprised of a twelve bedroom inn that dates back to the 13th century, and a 72 acre working farm. Vineyards and olive trees spread through rolling hills rising to a small valley. A stay at Santo Pietro is one of the best ways to enjoy all that Tuscany has to offer.

They serve wine from their vineyard, olive oil from their trees and vegetables from their garden- pretty awesome, right?! The service was impeccable and we all felt really at home while we were their. The rooms, grounds, food, wine, pool, etc. made for such a great stay!



Shortly after we arrived, RM, Sabrina and I headed back out to the city center to have dinner. I can’t remember the name of the restaurant the Inn suggested, but I will say we were so happy with their suggestion! The food was fantastic and it was a small, home-y type of place.


Also saw this gorgeous double rainbow on the way there!


On Tuesday, we had a winery tour of the Valdipiatta winery in Montepulciano, which is about 6KM from the Inn. Sabrina is in the wine industry and hooked us up with the tour and tasting since she knows the owner. It was fantastic! So interesting and the wines were incredible. We ended up taking 4 bottles with us, 3 of which they gifted, which was very generous.


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After, we toured the Pienza city center and then tried to go to lunch at a restaurant with amazing views of the land, but unfortunately we got hit with a massive thunder/lightening/hail storm which left us stranded in the van for 40 minutes!


We still had a great lunch, though! Once we got back to the Inn, we all napped, which was glorious. Once I woke up, I saddled up in their common area to read and have a glass of wine, obviously accompanied by snacks!

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We ended up eating dinner at the Inn, which was fantastic! Lots of delicious starters and an incredible Rabbit Ragu type of dish.

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So good! On Wednesday, after a quick workout we had breakfast and hit the road to visit Siena. Unfortunately, we got caught in massive traffic and it was a bit of a nightmare getting to the city center and finding parking. BUT, once we did it was all fine and good 🙂 RM and I decided to snag lunch alone, which was nice to have some catch-up time.

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yes, more pizza 😉

We walked around the rest of the city center and saw the Duomo, which was a beautiful building! We snagged drinks outside in the area where they used to do horse racing. Lastly, we grabbed a gelato before hitting the road back to our Inn.

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For dinner, the Inn was closed so we took another recommendation and went to 13 Gobbi in the charming town of Montefollonico, which was only about 5 mins from the Inn. I’ll preface this by saying that 13 Gobbi was everyone’s FAVORITE restaurant and had the absolute best food- and, coming from a group of true Italians must mean something! It was so good we went back the next night so Sabrina could experience what we were raving about (she was visiting a friend the first night we went). The owner/waiter was hilarious and a total character who made the dinner an event, not just a meal. Everything from the wine to the food to the desserts was unlike anything I’ve ever had, but the freshly made alfredo dish probably stole the show. They literally take hot pasta and cream and add it to a wheel of cheese, where they scrape from the sides to create a creamy, saucy pasta dish. I died a little. I’ll let the pictures do the rest of the talking, but I will say if you ever find yourself in that area, you MUST go there 🙂

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photo 1

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And now I want to go back… sigh….

As for our last day in Pienza, we went back to Montepulciano and spent the afternoon there before heading back and relaxing by the pool since it was FINALLY perfect weather.

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All in all, I really loved the second part of our trip- it was nice to be in a slower-paced environment and able to relax a little more, not to mention I loved checking out the little towns/cities in the area.

Phew- if you made it through this record-long post- thank you!! Next stop: Castiglione Della Pescaia. I hope you’re enjoying these recaps- it’s so fun for me to relive the vacation as I recap it… and nice to finally share all the photos we took!

Questions for you: What’s your favorite restaurant? Are you a big pasta fan? have you been to the Tuscany region of Italy?

8 thoughts on “Italy Recap Part 2: Pienza {including stops in Montepulciano & Siena}

  1. Jean Brennan says:

    Love reading of all the places you visited. Besides your expertise as a fitness instructor you certainly make a great tour guide!!

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