The Enchanting Small Towns of Southern Tuscany
Southern Tuscany is home to some of the most charming towns I’ve ever seen. Imagine walls adorned with vibrant flower pots, ancient fortresses, and houses painted in warm, gentle hues. Although Tuscany boasts beauty all around, this guide focuses on the southern part of the region.
For your road trip, I recommend to start from Siena, a gem of a town with its UNESCO Heritage Piazza and pastas so good I promise it will make you smile 😊. From there, set off to explore the enchanting landscapes and towns that define Southern Tuscany.
Mid-Southern Tuscany Towns: Siena and Downwards
Siena
Siena is a gem with its UNESCO Heritage Piazza, clock tower, and stunning Siena Cathedral—must-see highlights. The city’s relaxed atmosphere invites you to stroll slowly and enjoy its Gothic architecture. For a taste of local flavor, try a degustazione at Nannini, where you can enjoy delicious pastries and the city’s local sweets!
Montalcino
If there’s a wine that stands out from my trips to Tuscany, it’s Brunello di Montalcino. Montalcino is a must for any wine lover. Also, the town’s medieval fortress offers panoramic views of the surrounding vineyards. Exploring Montalcino’s winding streets and tasting its renowned wine is a divine experience.
San Quirico d’Orcia
San Quirico d’Orcia is a delightful village known for its beautiful gardens, including the Horti Leonini, designed by Diomede Leoni, a friend of the Medicis, which is why you’ll find his statue in the center. The town’s charm and peaceful atmosphere make it a perfect stop. After leaving San Quirico, enjoy the SP146 drive to Pienza, and make sure to stop at at Cappella della Madonna di Vitaleta.
Capella della Madonna di Vitaleta
Cappella della Madonna Vitaleta is a charming 12th-century chapel that you’ll come across while exploring the rolling hills of Val d’Orcia. Built by locals, it’s dedicated to the Madonna Vitaleta, an image of the Virgin Mary with the Child Jesus. The fact that it’s nestled in the middle of nowhere really helps you immerse yourself in the beauty of the Tuscan countryside.
Pienza
Pienza is not just about picturesque streets and delightful Pecorino cheese. The town’s cathedral, Pienza Cathedral (Cattedrale dell’Assunta), is a beautiful example of Renaissance architecture.
From the pubs and restaurants, you can enjoy stunning views of the Val d’Orcia, especially magical at sunset.
Montepulciano
Montepulciano is home to the beautiful Piazza Grande, the impressive Palazzo Comunale and the Renaissance San Biagio Church.
Don’t miss the chance to enjoy a coffee at Caffè Poliziano, where you can sip your drink while taking in an amazing view of the Val d’Orcia. Across the road, you can explore Maledetti Toscani, which offers a range of beautiful local Tuscan leather goods.
Cortona
Cortona is stunning, especially on foggy autumn mornings when the town’s elevated position offers incredible views. Its Etruscan history adds an intriguing layer to your visit, with ancient ruins and charming streets to explore. Don’t miss dining at La Bucaccia, a Michelin-starred restaurant renowned for its exceptional Tuscan cuisine.
If you’re a fan of the Conan O’Brien show, you might recognize Cortona from the episode featuring Jordan Schlansky, where it was highlighted as a unique destination.
Tuscany Further South: the Maremma Region
The Maremma region and Val d’Orcia both offer stunning landscapes, but they have their own distinct characteristics. Maremma is known for its diverse natural beauty, from rugged coastal cliffs and sandy beaches to rolling hills and relaxing thermal springs.
Sorano
Known for its rock-hewn architecture and ancient cave dwellings, Sorano offers a unique glimpse into the past. The Fortezza Orsini and the Vie Cave, a network of ancient Etruscan pathways, are major highlights. Sorano’s blend of history and natural beauty makes it a captivating destination.
Pitigliano
Pitigliano, perched dramatically on a cliffside, is a stunning blend of local and Jewish cultures. The town’s unique setting offersa charming atmosphere. You can wander through its streets to discover kosher wines, Jewish sweets, and unleavened bread, reflecting the rich history of the area. Local wineries produce excellent varieties like Bianco di Pitigliano DOC and Rosso Toscano that you can enjoy.
Don’t miss trying the migliaccio, a light crepe-like treat, or the sfratto di goym, a nut and honey biscuit with a fascinating backstory. Whether you’re soaking in the views from the cliffside or savoring traditional dishes, Pitigliano is a delightful destination that combines history, culture, and great food.
Sovana
Sovana is a charming medieval town with rich historical attractions. The Rocca Aldobrandesca, a prominent fortress, stands on the foundations of an 11th-century castle built by the Aldobrandeschi family. On the other side of town, St. Peter’s Cathedral, a key monument, showcases the transition from Romanesque to Gothic architecture. Stepping back further in time, the Sovana necropolis offers you a glimpse into Etruscan history with its tombs and architectures, which you would love if you’re into historical facts.
Saturnia
Known for its healing properties, the Saturnia Hot Spring is a great spot to unwind with friends, family or your partner. Legend has it that Zeus created the springs by striking the earth with a thunderbolt ⚡⚡, giving us these mineral-rich waters. The natural beauty and calming atmosphere are out of this world, though it can get pretty crowded, especially during peak times, So, it’s a good idea to go early and make the most of it.
An Epic Southern Tuscany Road Trip Itinerary
Starting from Siena Down South: Val d’Orcia Road Trip
Embarking on a road trip through the Val d’Orcia offers a fantastic way to experience the classic Southern Tuscan charm. Beginning in Siena, you’ll navigate scenic roads like the SP146 from San Quirico d’Orcia to Montepulciano, featuring calming green and golden rolling hills.
Your journey will take you from Siena to Montalcino, known for its Brunello di Montalcino wine, then to San Quirico d’Orcia, where you can visit the Horti Leonini garden. Don’t miss the picturesque Capella Vitaleta among rolling hills and cypress trees.
If you’re stopping for lunch in any town in Val d’Orcia, you absolutely have to try pici—it’s so good! This local pasta is hand-rolled into thick, round strands that give it a wonderfully chewy texture, making it perfect for soaking up rich, flavorful sauces.
Next, visit Pienza for stunning views of the Val d’Orcia from its pubs and restaurants, then head to Montepulciano, renowned for its Vino Nobile wine and charming piazzas. For the first night of your journey, stay in a hotel in either Pienza or Montepulciano to fully enjoy these charming villages.
PS: For an extra treat, consider a detour to Cortona, where you can savor fine dining at Osteria del Teatro and enjoy breathtaking views of the city and countryside from the Santa Maria delle Grazie chapel.
From Montepulciano Further Down South: the Maremma Region
From Montepulciano, head south to explore Sorano, with its rock-hewn architecture, and Pitigliano, often called “Little Jerusalem.” Next, visit Sovana, where the Sovana Necropolis offers a glimpse into ancient Etruscan history. Finally, relax at the Saturnia Hot Springs, known for their healing properties.
More Things to Do in Tuscany
⚜️ Be Charmed by the Beautiful Gardens in Florence, Italy
⚜️ Immerse Yourself in Chianti: Italy’s Charming Wine Region
⚜️ Witness Renaissance Art at Florence’s Galleries & Museums
⚜️ Experience San Miniato: Italy’s Graceful Hill Town & Truffle Haven
⚜️ Marvel at the San Gimignano’s Medieval Streets & Towers
Southern Tuscany Hotels: Where to Stay
The best base for exploring Mid-South Tuscany is Siena. Here are some great luxury and budget options:
Luxury Hotels in Siena
Hotel Certosa di Maggiano: Imagine staying in a former monastery where history meets modern comfort. The gardens are beautiful, and the peaceful vibe is perfect for relaxing and soaking in the Tuscan landscape.
Grand Hotel Continental Siena: This hotel is a real gem, set in a historic building that blends classic charm with modern touches. Plus, it’s right near Piazza del Campo, so you can easily explore all of Siena’s main attractions.
Budget Options in Siena
Hotel Italia: Just a short walk from Piazza del Campo, this place is all about convenience. The rooms are clean and simple, with everything you need for a budget-friendly stay.
Hotel Minerva: Cozy and well-kept, this hotel has rooms with modern touches that make for a comfortable stay. It’s budget-friendly, making it a great pick for travelers looking to save without sacrificing comfort.
For exploring the Maremma, you could find some accomodations in Pienza or Montepulciano.
FAQs
What is the best base city for exploring Southern Tuscany?
Siena is an excellent base for exploring Mid-South Tuscany due to its central location and is an amazing place to visit by itself. Afterwards, you can explore the mid-south region such as Montalcino, San Quirico, Pienza, and Montepulciano. You can try to find a hotel in Pienza / Montepulciano before venturing further south to experience the enchanting towns of Sorano, Pitigliano, Sovana, and Saturnia.
Do I need a car to explore Southern Tuscany?
Yes, having a car is highly recommended for exploring Southern Tuscany. Public transportation in this region can be limited, so having your own vehicle offers the freedom to stop whenever you want—whether it’s for a quick snack, a coffee break, or to snap a photo of a picturesque scene at your own pace.
What are some notable hot springs in Tuscany?
The Saturnia Hot Springs and Terme di Sorano are two of the most famous hot springs in Southern Tuscany, known for their natural beauty and therapeutic properties.
What is the most picturesque road in Tuscany?
The Val d’Orcia road trip is considered one of the most picturesque routes in Tuscany, offering stunning views of rolling hills, cypress-lined roads, and charming medieval towns. The SP146 is definitely among the most beautiful roads I have driven. Please make sure to make a stop and enjoy the charming Vitaleta Chapel 🙂
Where is Capella di Vitaleta located?
Capella di Vitaleta is located in the Val d’Orcia, between Pienza and San Quirico d’Orcia. This small chapel is one of the most photographed spots in Tuscany, set amidst a beautiful landscape of rolling hills and cypress trees.
The Finale: Visiting the Small Towns of Southern Tuscany
Seeing Southern Tuscany’s fairytale-like landscape, a sweet feeling will warm your heart, effortlessly curling your lips into a smile. You will be mesmerized by the views of these southern Tuscan towns🤍. Now that you’re familiar with the area, find a cozy place to stay and enjoy your journey through one of the most beautiful countrysides in the world