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Must Visit Towns in Tuscany, Italy

Writer's picture: Emily AnneEmily Anne

Updated: Oct 4, 2024

Tuscany is a dream destination renowned for its rolling hills, historic towns, and incredible wine. Its picturesque towns are full of medieval architecture and charming cobblestone streets. Art lovers, wine lovers, and those seeking peaceful escapes will all find something to enjoy in this region. If you're planning a trip to Tuscany, here are some must-see towns to make your visit unforgettable!


Best Tuscany, Italy Towns You Can't Miss


Chianti

The Chianti region is known for producing some of the best wine in the world and is dotted with quaint villages, scenic vineyards, and rolling green landscapes. One of the most popular towns in Chianti is Greve in Chianti, a charming village that serves as the gateway to the region.


A visit to Chianti isn't just about wine, though that's a big part! You can enjoy wine tastings at several prestigious wineries, such as Antinori nel Chianti Classico, where you can sip local varieties and tour their modern, architecturally stunning facility. Be sure to sample the signature Chianti Classico, a bold red wine that's synonymous with the region.


Afterward, treat yourself to an authentic Tuscan meal at Trattoria Sotto L'Arco, a favorite spot for locals and tourists alike. This cozy restaurant in Greve in Chianti offers an authentic taste of local cuisine, including handmade pasta and, of course, plenty of Chianti wine. Plan your visit in the late spring or early fall for the best weather and fewer crowds, making it an ideal time to explore the vineyards and villages at your own pace.



San Quirico d'Orcia & Pienza

To experience Tuscany's serene countryside, head to San Quirico d'Orcia and Pienza, two charming towns located in the heart of the Val d'Orcia. This area, a UNESCO World Heritage Site, is known for its breathtaking landscapes and quintessential Tuscan views, offering a tranquil escape from the hustle and bustle of city life.



San Quirico d'Orcia is a small town with medieval origins. It is perfect for wandering around its ancient streets and visiting landmarks like the Collegiata di San Quirico. If you're looking for a unique experience, don't miss the nearby Bagni San Filippo Hot Springs, a natural spa in the forest. It's a hidden gem where you can relax in warm, mineral-rich waters surrounded by nature.



Just a short drive away is Pienza, a Renaissance town famous for its pecorino cheese. Pienza's historic center is small but packed with charm. Be sure to stop by one of the many local shops for a sample of their renowned cheese or take in the stunning views of the Val d'Orcia from the town's panoramic terraces. The best time to visit these towns is during the spring, when the surrounding landscape is lush and green, and wildflowers dot the fields.


Montepulciano – The Vino Nobile VIP

Another gem in the Val d'Orcia, Montepulciano, is a hilltop town that oozes charm and history. Known for its Vino Nobile di Montepulciano, this town is a must-visit for wine and history lovers. The medieval and Renaissance architecture here is awe-inspiring, especially the Piazza Grande, which is lined with stunning palazzi and the towering Duomo.


Montepulciano is also a great place to sample local cuisine. Many restaurants offer traditional Tuscan dishes paired with the town's famous wine, creating the perfect culinary experience. If you're looking to dive into the local culture, try visiting during the Bravio delle Botti. This annual barrel-rolling race takes place in August and adds a festive touch to the town's vibrant atmosphere.


For a quieter experience, visit Montepulciano in the fall, when the vineyards surrounding the town are at their most colorful, and harvest season brings an abundance of local festivals and events.


Monterrigioni

Monteriggioni, a small medieval town, is a lesser-known but captivating destination. Surrounded by ancient walls and towers, this hilltop village offers one of the most well-preserved examples of medieval architecture in all of Tuscany.


Wandering through Monteriggioni's narrow streets feels like a trip through history, as much of the town has remained unchanged for centuries. Be sure to visit the Piazza Roma, the town's main square, where you'll find charming cafes and restaurants. Monteriggioni is also an ideal base for hiking, as it's located along the Via Francigena, a historic pilgrimage route.


While small, Monteriggioni's charm is undeniable. It's an excellent stop for travelers who want to escape the busier towns and enjoy the tranquility of Tuscany's countryside. Monteriggioni is an easy day trip from Siena, as it's just a short drive away.


A building in Monteriggioni's

San Gimignano

Known as the "Medieval Manhattan" because of its impressive skyline of medieval towers, San Gimignano is one of Tuscany's most famous towns. Its 14 towers, which date back to the 12th and 13th centuries, give the town a dramatic and unique appearance. Strolling through San Gimignano is like stepping back in time, as many buildings have been carefully preserved over the centuries.


The town is also famous for its Vernaccia di San Gimignano, a crisp white wine that pairs perfectly with local dishes. While visiting, you can also climb the Torre Grossa, the tallest of the remaining towers, for panoramic views of the surrounding countryside. Another must-visit is the Collegiata di San Gimignano, a Romanesque church with stunning frescoes that depict stories from the Old and New Testaments.


San Gimignano is especially popular with day-trippers, so plan your visit early in the morning or later in the evening to avoid the crowds and fully appreciate its beauty. If you're a fan of gelato, make sure to stop by Gelateria Dondoli. This award-winning gelato shop offers some of the best flavors in Tuscany.


San Gimignano, the Town of Fine Towers in the distance

Conclusion

Tuscany is home to some of Italy's most beautiful and historic towns. From the wine-soaked hills of Chianti to the medieval towers of San Gimignano, each destination offers a blend of history, culture, and natural beauty. The wine, architecture, and stunning countryside are just a few reasons why these must-see towns in Tuscany should definitely be on your itinerary. Take the time to explore each one, and you'll discover the true magic of this incredible region.


If you've visited any of these Tuscan towns, let me know in the comments which one was your favorite!

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Emily in Alberobello

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I'M EMILY

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I'm a Seattle-based travel blogger who loves to wander the world in search of delightz - like great food, kind people, amazing views, local art, hidden gems, cute dogs, and other unexpected discoveries in new places!

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