Our trip to Tuscany was dreamy. Like every good vacation, ours started with sitting eight hours in the car. Two rest stops, one near death experience (Italian driving!) and miles of gorgeous scenery later, we finally arrived in Siena.
We chose an apartment just at the edge of the old town where we could explore the city by foot but still have a place to park our car. The parking space tends to become increasingly important with each stop due to the inverse relationship between the number of days we have left of our vacation and the number of bottles of wine we are lugging around.
On our first morning in Siena, we stumbled upon Torrefazione Fiorella, a delightful little coffee bar with pile of fresh pastries on the counter. Every Italian fantasy I’ve ever had was fulfilled–a great cast of characters, impeccably dressed, bantering over foamy cappuccinos (naturally everyone lit up immediately upon leaving the cafe). Each morning, we parked ourself at the counter in the back and deluded ourselves into thinking we were locals.
Remembering my amazing wine tour experience in the south of France, I was excited to use this trip to learn more about Tuscan wine. I scoured the internet for a a knowledgeable guide, and after much searching, I (appeared to have) finally found one. Unfortunately, the day of the tour the guide got sick and sent a driver for us instead. The driver spoke English about as well as we speak Italian (not very) and knew next to nothing about wine. Still, he was very friendly and was intent on making sure we had a good time.
Despite the fact that the tour was not nearly as educational as we had hoped or anticipated, we did taste some great wine and had fun visiting with the producers. Our favorite wineries from the trip were Castello Monterinaldi and Querceto de Castellina.
At both wineries, we were welcomed by a knowledgeable member of the team who explained the winery’s production and walked us around the gorgeous grounds.
The next day, after our obligatory cappuccino at our (now) regular haunt, we headed for the cathedral. The massive black and white marble columns are one of the only things I remember from my college art history class, so I was pretty psyched to see them up close. (Plus, I felt so cultured…)
I could have stayed in the Piccolomini Library all day, but was soon shoed out by another group of (obvious) connoisseurs of the arts waving their selfie sticks in my face and vying for the best spot to snap a few photos with their iphones.
Fortunately, we arrived in Siena a few days before Easter and missed (just barely) the massive tsunami of tourists that washes over all of Italy during the summer. While we hardly had the place to ourselves the lines were very reasonable. We decided to take advantage of the short wait times and sign up for the la porta di cielo tour, which offered the opportunity to tromp around the eaves of the cathedral. Seeing Siena from the cathedral’s rooftop and peeking down into the knave from the rafters was an experience I’ll never forget.
We spent the rest of the day wandering around the city, enjoying the sunshine, and drinking in the architecture.
On our first night, we had a lovely dinner at Enoteca i Terzi, a cozy wine bar with delicious tuscan dishes. The waiter was very friendly and helped us navigate their massive wine selection, which, after the eight hour drive, we very much appreciated.
Our wine tour included lunch at one of the wineries (the winery and the lunch were just meh) so we weren’t famished when we got back to Siena. Still, as the evening progressed, snacks were in order. We were very impressed by the little market in the city center, Consorzio Agrario Siena. The shelves were stocked with local wine, cured meats, cheese, and tuscan sweets. They also had a small produce section and a delightful bakery with fresh bread, homemade pizza, and a bajillion kinds of biscotti. (We discovered biscotti dipped in sweet vin santo on this trip…I don’t know what took us so long.)
On our last day, we stopped for lunch at Gino Cacino di Angelo, an incredible deli with fresh sandwiches and an impressive selection of wine. We asked the proprietor to select his favorite cured meats, cheeses, etc for us and then sat back with a glass of prossecco while we waited for him to work his magic. We were sad we didn’t stop by earlier!
Three days in Siena was definitely enough to explore the main sights of the city and even take a small excursion in to the country side. We spent the next few days wandering through some of Tuscany’s hill towns and then made our way to Florence.
Accommodation in Siena
La Casa di Roy Dentro le Mura (Airbnb)
Perfect host, convenient location, off street parking.
Eating in Siena
Enoteca i Terzi
Delightful wine bar serving traditional Tuscan food. Impressive wine list.
Via dei Termini 7m 53100, Siena, Italy | +39 0 577 44 329
Delicious charcuterie, great sandwiches, and large selection of wine. Perfect for lunch. The entrance is covered with ivy, so it’s a little difficult to find. Absolutely not to be missed.
Piazza Del Mercato 31, 53100, Siena, Italy | +39 0 577 223 076
Cute coffee bar (standing room only) with perfectly silky cappuccinos and yummy pastries.
Via di Citta 13, 53100, Siena, Italy | +39 0 577 271 255