This fall we were able to take a trip out to Tuscany to visit our wedding venue, experience our menu tasting, and explore Pienza & surrounding towns in the Tuscan countryside. We wanted to share our itinerary with you as we hope it may inspire your trip as well! Below was our daily travel agenda, restaurants we ate endless pasta and wine at, and adventures we went on.
Day 1
For us the best way to get to Italy was to fly from LAX into Florence. We had an hour layover in Zurich, which was fun to revisit since it was the first time we were in Switzerland since we got engaged there in September 2023. We arrived in Florence around 6pm, took a quick shuttle to Avis rental, and hopped on the road down to Pienza. This was about an hour and a half drive. We would recommend you to arrive earlier than evening so you can avoid driving in the dark like we did.
Though the night drive paid off. As soon as we arrived in Pienza town we met our Airbnb hosts at their farm stay just outside of the town, Podre San Gregorio, where we parked our car. Driving in the actual town center is not possible, so you have to park outside of town and then walk in if you are staying in the center of town like we were. Nicco also had left us some charcuterie from his family farm such as Pienza pecorino cheese, cold cuts, fresh olives, and homemade olive oil. We enjoyed the charcuterie in our charming Airbnb while we planned for the week over a bottle of Nicco’s wine.
Day 2
The next day we had our morning coffee out on the balcony over a small square. We visited in off season so it was a quite morning only accompanied by the noises of the bells, we never quite figured out the timing on those.
Pienza is a hill town so there are wonderful views all around of the endless rolling farm fields & famous Val D’Orcia trees (you may have recognized these on our invitations). We adventured over to the outside of the town to the famous gladiator walk (1.5km). From the bottom of the valley of this walk you can look back and see Pienza in all it’s glory. It was incredibly peaceful, we spent some time here just enjoying the sounds of nature around us… and also taking gladiator reenactment pictures.
After exploring the area, we stopped for lunch in town at Trattoria Latte Di Luna. This restaurant is only open for lunch and is well worth the visit. Ed got a roasted pig, apparently the best in the region, and Jakky got the pasta pomodoro. We absolutely love truffle and since it was truffle season, we also split some truffle and cheese crostini.
Later that day we took a ~15 minute hilly drive over to the small medieval village of Monticchiello. It took us just about 30 minutes to walk around the village. We also explored a path along the outer walls of the fortress surrounding the village. It was like being back in the medieval ages! When we got back to Pienza we watched sunset and then we went to dinner that night at Ristorante Il Rossellino.
Day 3
Venue visit day! But not before a waking up for sunrise and watching the sun come up over the hills of Val d’Orcia. We would definitely recommend making it to sunrise on one of the days you are in Pienza. The valleys are filled with a beautiful mist with little Borgos and Hamlets poking through the tops, the colors of the hills come out differently than they do during sunset.
After sunrise we actually headed over to the local Coop (grocery store) to try to find some Eggs. Eggs are very hard to find it turns out in Italy unless you are getting them from a local farm. We were out of luck at the Coop, Jakky got to practice her Italian asking about egg availability, but we were in luck as Nicco said he could bring us some from his farm.
After breakfast and coffee we headed over to Borgo Sant’Ambrogio. The drive over is about 15 minutes from Pienza town through country roads lined with a gorgeous variety of trees ranging from Oak, Maple, and Cypress. Along the drive there are also many wineries. When we got to the Borgo we were met by our fabulous wedding planner Guilia who accompanied us on the tour. The villa was beautiful in the fall with all of the changing leaves. The secret garden where we will have our ceremony looks out over the rolling hills and out to Pienza in the distance. We checked out the dinner, dancing, cocktail areas - all different than the next and unique in their own way. We got so excited picturing all of our family and friends there with us in May.
After the visit we decided to go visit Montepulciano about 20 minutes away. The drive into Montepulciano is quite grand. There is a large church at the base of the hill, and at the top of the hill a perfectly picturesque medieval Tuscan town. Montepulciano is a bit larger than Pienza and sits up higher on the hills, it is famous for wine. We got lunch & spent a couple hours strolling around and checking out shops.
On the way back we paid a visit over to Chapel of the Madonna di Vitaleta. This was one of our favorite sites on the trip and you should absolutely visit, it is very close to Pienza town. The small chapel, framed by two rows of cypress trees was built in the spot where legend says the Virgin Mary appeared to a shepherdess. In 1533, a statue of the Virgin Mary by Andrea della Robbia was installed in the church. It is very spiritual feeling when you walk over and just stunning especially during golden hour.
That night we went to Jakky’s favorite restaurant of the trip Farmhouse "Poderuccio" it’s right at the bottom of Pienza so at night you can see all of the town lit up. The restaurant is completely family run. The owner brought us assortment of grappa and limoncello. The owner’s take great care into their food and it is obvious once you taste the dishes. The food was incredibly fresh, we got Wild Boar Pappardelle, Sage and Ricotta Ravioli, and a very tasty garden salad.
Day 4
The next day was filled with FOOD. We drove up to Florence for our menu tasting. This was an absolute highlight of our trip. The tasting took about half the day, as Italians are serious about their food and take have many more courses than we are used to.
Here is a mini sneak peak of what we tasted: Cocktail Hugo, Finger foods including beef tartare with quail egg and truffle (Ed’s favorite), Eggplants Parmigiana mini millefeuille (the Portelli family loves eggplant), Medallion of corn with burrata cheese and caramelized onion. About 7 different cheeses such as buffalo Mozzarella, Smoked burrata cheese, too many different kinds of pecorino cheeses to count. Assortment of “Il Norcino” (cold cuts and cured hams). Handmade pastas with truffles and raw tomatoes. Beef fillets with Brunello di Montalcino. Otto Muri Toscano Fiano IGT wine.
By the time we got back to Pienza, we had time for a long walk and then figured we may as well top off the feast of a day at La Bandita Townhouse restaurant. This restaurant is said to have the best burger in the area - which we can say with full confidence was great!
Day 5
On day 5 we stayed local since we had a wedding appointment in the afternoon in town. We walked all along the outskirts of Pienza where most of the locals from town live. There are only a handful of blocks in this area, and we watched people go about their daily lives hanging laundry from clothing lines, sitting on their porch drinking coffee, animals & children playing in the fall leaves in their yards. We meandered over to a historic nunnery that was still operational, we were invited to go inside - this was a new experience for us! There is a small chapel just past the nunnery which is lined with tall trees and has a beautiful rustic bell on the top. Both the nunnery and the chapel sit over a gorgeous view of the rolling hills below.
Luccinao had invited us over to his farm for a tasting that night. We got to see how he made Vin Sano wine (also the name of his barn cat in our pictures), grappa, as well as fresh olive oil. This was such a special experience to see how a family makes these goods and operates their small business from home. Luccinao is such comical man who loves to joke and ask questions, we had a blast conversating over our translator apps together.
Lucciano made us Tuscan Bean Soup, brought us out an assortment of pecorino cheese and cold cuts from his farm, grappa, and of course his fresh olive oil and wine! After laughing, exchanging stories about our lives, and many bottles of wine - Lucciano turned up the music and we danced all night in the kitchen. It was truly an unforgettable experience.
