One Week in Tuscany
During our week in Tuscany, we visited quite a few different historic, hilltop towns in between days of lounging poolside drinking limoncello. Here's a recap of our day trips to Tuscan towns.
General Thoughts
A car is necessary for exploring Tuscany. All of the charming medieval villages and wineries are found in the countryside. Opt for a small car in order to more easily navigate narrow roads.
Most of the medieval hilltop towns are actually car free - once you arrive, you park outside the walls and walk up into the town.
If you're only visiting for a couple days, consider staying at a beautiful estate like Castello Banfi or Castiglion del Bosco. If you're staying for a longer timeframe or on a tighter budget, opt for an agriturismo or Airbnb - there's plenty of charming Tuscan farmhouses available!
If you're interested in visiting wineries, do your research! Different areas in the region specialize in different types of wine, so it's best to try a variety of Tuscan wines and narrow in on your favorites. Most wineries also require a reservation to visit, tour, and taste, so book in advance.
Montepulciano
This was the first town we visited. Unfortunately, we were both battling colds and a rough first day, but we still enjoyed exploring the town and having lunch.
Montepulciano is a medieval town south of Siena known for its wine Vino Nobile.
We started our day with treats from Laboratorio del Cioccolato, which were AMAZING. After trying a couple wines from the area at an enoteca, we picked up a bottle of Rosso di Montepulciano to enjoy later in the week.
Before leaving to visit neighboring Pienza, we had lunch outdoors and enjoyed a Tuscan soup called ribollita.
Pienza
One word: PECORINO! Pienza is the home of pecorino, a cheese I didn't realize I loved so much (which, if you know how much cheese I consume, is saying something). Pecorino is prominent in Tuscan cooking, which we found not only on antipasti charcuterie platters, but also within pastas (like ravioli) and sandwiched within paninis.
Pienza is a smaller, pretty village, loaded with cheese shops (caciotecas) that feature pecorino. It sits near Montalcino and Montepulciano, in between the two towns.
To enjoy their sheep's milk bounty, start with a cheese tasting and glass of wine at an enoteca, then visit a couple cheese shops like Marusco e Maria to snag your favorite type of pecorino to take home. We picked up a sizable chunk for only €3!
San Gimignano
For most of our time in Tuscany, we stayed at an agristurismo about 10 minutes outside of San Gimignano, so we spent a couple afternoons and evenings exploring the town.
Of all the towns we visited, this was our favorite. I had been skeptical since it seemed to be the most popular/touristy, but it was truly tops. If you only have time to visit one town in Tuscany, I would recommend San G.
San Gimignano is distinctive with its skyline of multiple medieval towers. It's a well-maintained 13th century town full of restaurants and shops highlighting the best of the Tuscany region including wines, cheese, and meats.
We enjoyed amazing meals, including a romantic dinner outdoors at Le Vecchi Mura with delicious wild boar ragu tagliatelle (which made its way into our top pasta rankings!). San Gimignano is also home to an award-winning "world champion" gelateria (Gelateria Dondoli), which we enjoyed more than once!
Siena
Siena was lovely! It's an actual city, larger than the other little towns, but still felt quaint and charming. Compared to Florence’s overwhelmingly busy streets, Siena offers the ability to find solitude while wandering.
The Piazza del Campo was beautiful. Enjoying the sunshine and people watching by having a drink at one of the many restaurants and bars lining the piazza is a must. Another essential stop in Siena is the impressive Duomo. You can find a great panoramic view of the city from the top of the Duomo's arched wall, which is included in the Duomo museum ticket (accessed through the Museo dell'Opera).
After exploring Siena in the afternoon and enjoying apertivo at Il Bar Pario at the piazza, we ended up at Osteria la Sosta de Violante for dinner, which was a delight! We enjoyed everything we ordered: Pecorino cheese fritters with pear sauce, eggplant parmesan with buffalo mozzarella in a jar, and pici pork ragu.
Chianti (Montefioralle, Greve, Panzano, Castellina in Chianti)
We chose one day to explore Chianti and made the most of it, with reservations at two different wineries and a plan for lunch in between.
We were on the road by 8:30am, even having had breakfast, which is impressive for us! Our first stop was a tiny wine producer in Montefioralle, near Greve. Azienda Agricola Montefioralle is a small producer, and we had our own private tour and tasting. It was relaxing and interesting, and the perfect way to ease into the day. We learned a lot about Chianti wine and designations, but the best part was the Vin Santo, a dessert wine. It was delicious, and we had the chance to see future vin Santo grapes hanging in the attic of the winery!
Before leaving Montefioralle, we wandered the tiny, charming village and made a pitstop to take photos in front of Jeff's namesake restaurant - “La Castellana”!
For lunch, we went to Panzano to visit “the butcher in Chianti” for a meaty, pasta-less meal. We grabbed a glass of wine at a nearby bistro called Enoteca Il Cardo before heading to our next wine tasting at Castello di Verrazzano. This winery was a nice contrast to our first winery visit - it was much bigger, with a restaurant on site and full tour groups. It was interesting and entertaining, though we both agreed we preferred the first winery experience.
We stopped in Castellina in Chianti, another small, cute town, before heading home. The Chianti landscape is beautiful and much more mountainous than either of us expected.
Montalcino
The last town we visited was Montalcino, which is known for Brunello wine (which we wanted to taste more of!).
Montalcino was super charming and the number of people roaming the streets was sparse, which we loved! We knew we wanted to visit an enoteca to try different Brunello wines since we weren't visiting any wineries, but wanted to ease in and start with a light lunch first. After wandering the streets for awhile to explore, we stopped off for lunch outdoors near Piazza del Polpolo at a charming spot called Alle Logge di Piazza. We each tried a glass of Brunello to accompany our salad and small plate of charcuterie. Our table allowed for great people watching!
The number of enotecas for Brunello wine tastings was overwhelming! It reminded us of St. Emilion in Bordeaux. After some quick research, we opted to go to the Fortezza which had an on-site enoteca, so we ended up wine tasting at a castle! We sat outside and ordered a tasting of five different Brunello wines. The waiter was super helpful, giving us a brief overview and history of Brunello, as well as two extra tastings. We left with a bottle of our favorite to enjoy while on the road.
It was fun to spend a week in Tuscany, a place many of our friends and family had visited, to explore charming, medieval hilltop towns, enjoy the countryside, and taste great Italian wines!
