It’s been less than two years since our last visit to this tiny Renaissance town famous for Pecorino cheese and we’re back for a wedding celebration!
Tommaso and I visited Pienza in fall 2023 during our Italian roadtrip—who would’ve thought we’d be back so soon?! This time, it was for the wedding of one of Tommaso’s old classmates. We stayed in Pienza at one of the very few hotels in town, Hotel San Gregorio. While the room was a bit dated, it was spacious, extremely clean, and even had a pool (definitely a perk during a July heat wave).
Before getting ready for the night, Tommaso stopped by a bar and asked for an iced coffee which they served in a martini glass. It was comical.
Fancy Presentation For His Iced Coffee!
That first evening was a casual welcome cocktail hour at a nearby bar where guests mingled over drinks with a stunning backdrop of rolling Tuscan hills.
Afterward, a large group of us went to dinner at a local restaurant. Somehow, I didn’t take any pictures but I ordered a delicious pici dish (a pasta shape typical of this region) with a simple tomato garlic sauce.
The following day was the wedding and we didn’t do much during the day since we were still a little jet-lagged. Of course, I took hours to get ready while Tommaso napped…typical. Naturally, we had to snap a few photos before heading to the event.
The weather was unusually hot for early July, high 90°s, so Tommaso was suffering in his suit. I’m shocked my makeup didn’t budge considering I was in full glam (the powder and setting spray were putting in work)! The ceremony began at 5 PM at Pienza’s town hall in the main piazza. Since the space inside is limited, only close friends and family attended the ceremony itself, while the rest of us waited outside.
After the vows, everyone gathered for a group photo in front of the cathedral.
Congratulations to Virgina and Alex!
Following the ceremony, we were all shuttled to Borgo Sant’Ambrogio in the nearby town of Trequanda, a stunning resort nestled in the hills. The elevated setting brought cooler, more comfortable temperatures.
Upon arrival, cocktail hour began with tables of Italian cheeses and cured meats (there was a smoked melty cheese that I still dream about). There were also over ten types of passed canapés and while I didn’t snap any photos, trust me—they were scrumptious. Some of my favorites included mini Mortadella pistachio paninis, vegetable fritto misto, Mozzarella in carrozza, pappa al pomodoro, and lampredotto, just to name a few.
We couldn’t resist sneaking in a few more photos before dinner. The setting was too gorgeous to pass up.
Dinner was served at a long communal table with a lovely tablescape of various flowers and candles.
The Long Communal Table.
The menu featured traditional Tuscan elements like wild boar ragù and a Chianti Classico jus for the main dish.
Menu.
Paccheri with Tomato and Burrata Cheese.
Pappardelle with Wild Boar Ragù.
Filet Mignon with Chianti Classico Jus and Hasselback Potato with a Side Salad of Arugula, Pear, Walnuts, and Parmigiano Reggiano.
Overall, the food from cocktail hour to the seated dinner was solid. I was pretty full from all the canapés and pasta dishes, so I barely touched my filet mignon, but Tommaso happily finished every course.
At one point during dinner, I had to snap a photo of Tommaso with all his old school girlfriends.
The St. George’s Crew Reunited.
After dinner, the bride’s father surprised everyone by performing with a live band as he was once part of a popular Italian group!
Of course, Tommaso and I were patiently waiting for dessert. No Italian wedding would be complete without millefoglie, a traditional layered pastry. Millefoglie, which means “a thousand leaves” in Italian, is known for its crispy puff pastry layers, rich cream, and topping of fresh fruit and powdered sugar. It’s a symbolic wedding dessert representing love and unity. While I typically prefer a classic cake, this was one of the best millefoglies I’ve ever had.
The Millefoglie Wedding Cake.
There were also mini Italian pastries (known as mignonettes or mignons) that were absolutely delicious and of course we tried every single one.
The rest of the evening was filled with dancing under the stars until we finally caught the shuttle back to Pienza in the early hours of the morning.
The next morning, we took it easy: breakfast at the hotel, a quick dip in the pool, and then a leisurely stroll through Pienza’s charming streets.
We even returned to the same cheese shop we’d visited on our last trip and picked up a few goodies to bring home.
We wrapped up our stay with one last dinner with friends, another moment I somehow didn’t capture in photos. It was the perfect ending to a few days filled with beauty, love, and a whole lot of pasta.