Nestled in the heart of Italy, the Tuscan Countryside is an idyllic destination for a day trip from Siena. Touring the Tuscany Countryside is one of the loveliest experiences you can have in Italy. The area is renowned for its picturesque rolling hills, and its hill towns are some of the most beautiful in the country. On a tour of the Tuscan countryside, you’ll get to see traditional farms and vineyards. You’ll also have the opportunity to sample some of the region’s famous wines and cheeses. So whether you’re looking for a relaxing day trip or an adventure-filled vacation, a tour of the Tuscan countryside is sure to please.
First, before we dive into the best places to visit in the Tuscan Countryside, let’s discuss the logistics of embarking on a tour of the Tuscan Countryside:
- Starting a day tour from Florence may be a stretch. To maximize your time, we recommend staying in Siena or an Agritourism b&b in the Val d’ Orcia region of Tuscany.
- You will need a car as there is no public transportation in the countryside.
Best Places To Visit in The Tuscan Countryside
Below is the route we took on our tour of the Tuscan Countryside. To make the best of your time, set off as early as 8am (we set off at 10am and felt like we were rushing).
1st Stop – Cugusi Silvana Farm
Cugusi Silvana Farm is located near Montepulciano and Val d’ Orcia region. This region is well known for pecorino (sheep’s cheese) and wine. At Cugusi Silvana Farm, you select from a wide variety of cheeses, cold cuts, and wine that you would like added to your picnic basket. The picnic basket includes a cheese board, bread, disposable plates, cups, and placemats. All picnic spots have a spectacular view of the valley, and you can see Montepulciano in the distance perched on a hilltop. All-in-all, this was an unforgettable experience for ~30 Euros (3ppl).
2nd Stop – Montepulciano
Montepulciano is a beautiful medieval hill town in southern Tuscany. The town is best known for its red wine, which has been produced here since the 14th century. Montepulciano is surrounded by vineyards and olive groves, and the town is full of narrow streets and historic buildings. We explored the beautiful Cathedral Saint Mary Of The Assumption in Piazza Grande. Across the Piazza is the Comune di Montepulciano where we climbed the steep steps up the tower to see the incredible view of the town and the valley.
3rd Stop – Pienza
Just a short drive from the city of Montepulciano is the picturesque town of Pienza. A fun fact about Pienza: Pope Pius II had this entire village rebuilt in the 15th century as an ideal Rennaisance town and named it Pienza (city of Pius) and intended it as a vacation retreat from Rome. As soon as we got to this town, we had lunch at one of the several restaurants in Pienza. Despite its small size, this town has soo much charm. We enjoyed wandering the town’s main street and popping into one of the many delightful shops. On the village’s south side is the Punto Panaramico, where you can see the incredible view of the valley. Pienza’s idyllic setting makes for the perfect stop on your tour of the Tuscan Countryside.
All in all, our day trip to the Tuscan Countryside was a resounding success! We saw a lot of beautiful scenery, tried some delicious cheese, food, and wine, and got to meet some friendly locals. Even though we only had a limited time to explore, we packed a lot into our itinerary. We left feeling like we’d really tasted life in Tuscany. If you ever have the chance to visit this part of Italy, don’t hesitate – it’s definitely worth the trip!
If you enjoyed this blog post, I’d love to connect with you on Instagram or TikTok. Also check out other articles from our trip to Italy ❤️