Tuscany is everything you imagine Italy to be—rolling hills dotted with cypress trees, sun-soaked vineyards, and towns that look frozen in time. Beyond Florence and Siena, there are dozens of smaller towns just waiting to be discovered, each with its own unique charm and breathtaking views. Whether you’re dreaming of cobblestone streets, quiet piazzas, or a glass of wine with a view, these are the most beautiful towns in Tuscany to spark your wanderlust.
Montalcino
Montalcino is a stunning town located in the Tuscan region of Italy, renowned for its world-famous Brunello di Montalcino wine and diverse natural beauty. Nestled among rolling hills, this picturesque town offers visitors a unique opportunity to immerse themselves in traditional Italian culture while exploring its charming cobblestone streets and fascinating historical sites.
Cortona
Cortona sits high on a hill with sweeping views over the Val di Chiana and Lake Trasimeno. Its stone streets, ancient walls, and charming piazzas give it an old-world feel that’s hard to resist. Art lovers and foodies alike will find plenty to enjoy here, from museums to local wine and truffles.
Lucca
Lucca is a walled city with a laid-back vibe and Renaissance beauty around every corner. You can walk or bike the entire loop of the city walls, which now serve as a leafy promenade. Inside, quiet streets, lovely churches, and little cafes make it perfect for a slow afternoon stroll.
Fosdinovo
Fosdinovo is a lesser-known town tucked into the northern hills of Tuscany, near the Ligurian border. Its medieval castle looms over the town and offers panoramic views all the way to the sea. The quiet, rustic charm here feels like a step back in time—perfect for travelers looking to get off the beaten path.
Montepulciano
Montepulciano rises from the hills like a fairytale fortress, with winding streets that climb past elegant palazzos and hidden wine cellars. It’s famous for Vino Nobile, one of Tuscany’s top wines, which you can sip while gazing out over rolling vineyards. The town is a dream for photographers, with views and architecture that steal the show.
Barga
Barga is a colorful town tucked into the mountainous Garfagnana region, far from Tuscany’s tourist trail. It has Scottish roots, a vibrant arts scene, and one of the best duomos in the region perched at the top of the hill. Narrow alleys and panoramic spots make it a peaceful place to wander and unwind.
Pitigliano
Pitigliano is one of the most striking of all Tuscan towns, partly because it’s located on a bluff between Lazio and Tuscany, which means the whole town from a distance looks as if it’s rising out of the rock face. Its impressive appearance is even more amazing when you consider that it was built by members of the Etruscan civilization many centuries ago, and you can still see where adjustments were made during the Roman era. To truly appreciate Pitigliano, you have to walk through the cobblestone streets and explore the stone staircases along the way.
Volterra
Volterra is located to the west of the region and it’s one of the most richly historical towns in the whole of Tuscany. Volterra, like Pitigliano and many other towns in the region of Tuscany, was constructed by the Romans and home to the Etruscans. The town has preserved much of its authentic Medieval architecture, including roofs made from red tiles, streets paved with cobblestones and gateways that, despite crumbling in some places, have remained standing for centuries.
San Gimignano
San Gimignano is home to some of the most impressive architecture in Italy, both in terms of size and style, so if you’re a fan of ancient Etruscan and Roman construction, you’ll really enjoy your time in this unique Tuscan town. There are no less than 15 towers in San Gimignano, and each one is breathtakingly stunning. One of the best things about San Gimignano is that it’s only a short drive from the city of Siena, which should be part of any good Italian itinerary, so it’s easy to pass through San Gimignano spontaneously on your travels without deviating from your planned route.
Pienza
Pienza is a tiny Renaissance gem perched in the heart of the Val d’Orcia. Known for its perfectly planned layout and romantic streets, it feels like stepping into a living postcard. Don’t miss the views from the town walls or a taste of the famous pecorino cheese that’s been made here for centuries.
Anghiari
Anghiari is a perfectly preserved hill town with stone houses stacked along narrow, twisting lanes. It’s famous for the Battle of Anghiari, once depicted by Leonardo da Vinci, and has a strong artisan tradition that lives on in local workshops. The setting above the Tiber Valley is pure Tuscan magic.
Siena
Siena, Italy, is located in the heart of Tuscany and stands proudly on the hillside. The piazza del campo is the centerpiece of it all, and wandering around Siena from there is a treat for the eyes, as Siena is one of the most beautiful medieval cities in Europe. The architecture is stunning. Get an even more amazing view by climbing to the top of the Torre del Mangia, a tower that was built in 1338, located in the Piazza del Campo. Siena is also an epicenter of wine in Tuscany, from where you can take many day trips for wine tasting and food.
Florence
Florence is the capital of Tuscany and one of the most beautiful cities in the world. It is renowned for its incredible art, culture and architecture and has been a popular destination for travelers for centuries. It’s rich history can be seen throughout its iconic landmarks such as Brunelleschi’s Duomo, the Ponte Vecchio and the Uffizi Gallery.
Monteriggioni
Monteriggioni is a picturesque town situated on a hilltop along the Via Francigena pilgrimage route. It is surrounded by an ancient wall that dates back to the 13th century. Today, Monteriggioni is known for its beautiful architecture and stunning views of rolling hills and vineyards below. The town has been immortalized in famous works such as Dante Alighieri’s Divine Comedy and Machiavelli’s Discourses on Livy due to its historical importance within Tuscany.
Collodi
Collodi is a small town best known as the home of Carlo Collodi, the author of the beloved children’s story Pinocchio. Situated on a hillside, this picturesque village has breathtaking views over the surrounding countryside. The town’s main attraction is the Collodi Pinocchio Park, a theme park dedicated to Carlo Collodi’s most famous creation. It’s also home to Palazzo Pretorio and Villa Garzoni, both of which are located in the city’s old town center. The former was built during the 13th century while the latter dates back to 1656.
San Quirico d’Orcia
San Quirico d’Orcia is a beautiful hilltop town in the Val d’Orcia region of Tuscany. Located just south of Siena, the town boasts stunning views of rolling hills and vineyards. The streets of San Quirico are lined with traditional stone buildings, many dating back to the Middle Ages. One of the most prominent features of the town is its Roman church, Santi Quirico e Giulitta, which was built during the 12th century.
Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.