Tuscany is far more than Florence’s Renaissance splendor or the rolling vineyards of Chianti — it’s a mosaic of medieval hill towns, coastal escapes, and quiet hamlets where time seems to slow down. Each corner of this region tells a different story — of art, food, wine, and timeless beauty. Whether you’re chasing sunsets over the Val d’Orcia, wandering through walled towns like Lucca, or soaking in the thermal waters of Bagno Vignoni, there are a lot of picturesque towns in Tuscany to explore, and fall in love with the region, one small town at a time.
Pitigliano
We start this list of the most picturesque towns in Tuscany with Pitigliano. Hanging off a cliff in southern Tuscany, Pitigliano is among the most picturesque towns in the area. It was called Little Jerusalem, and it used to host a thriving Jewish community that settled here in the 14th century. Tourists get an opportunity to see the old synagogue and the Jewish quarter, which remain well-preserved, and enjoy the ancient Etruscan backgrounds of the town, including an impressive archaeological museum and old cave ways cut in tufa rock.
Stroll through the small lanes, admiring the Orsini Fortress, the aqueduct, and the Cathedral of Saints Peter and Paul. Pitigliano can be easily combined with a trip to the neighboring Sovana and Sorano in the so-called tufa triangle.
Where to stay: Agriturismo Tenuta Roccaccia, La Casa degli Archi, or Locanda Il Tufo Rosa are all beautiful countryside accommodation options with views of the gorgeous rolling hills of southern Tuscany.
San Gusmè
San Gusmè is a small Tuscan village, isolated in the hills of Chianti, close to Castelnuovo Berardenga. It’s surrounded by vineyards, cypress trees, and it is the sort of place where time appears to stand still. The old walls and stone pavements culminate in a small central square where community people get together during the summer to watch films outdoors, and the town is also home to one of the quirkiest sights in Tuscany, an iconic statue of a man in flagrante delicto of defecating himself. San Gusmè is an ideal day trip destination, which can be combined with a Chianti wine-tasting trip or with a longer trip to Siena which is also close by.
Where to stay: Villa Curina Resort, Castello di Bossi, or Agriturismo Amina are all beautiful countryside locations and offer an experience with local wine.
Cetona
Located at the foot of Mount Cetona in southern Tuscany, this is a lovely town with its main hub being the Renaissance-style Piazza Garibaldi, which is one of the most beautiful piazzas in the area. The top town’s skyline is dominated by the old fortress and the beautiful Church of San Michele Arcangelo. The town is also home to the prehistoric Belverde Caves, giving the town the perfect balance between small-town vibes, culture, and elegance. Cetona has also become known in its artisan stores, olive oil, and truffles, making it a perfect break between Montepulciano and Città della Pieve.
What to do: Visit Agriturismo Il Caio, Fattoria del Colle, or La Torretta to have a nice stay in the vineyard and olive garden.
Radicofani
Rising over the Val d’Orcia, Radicofani can be seen miles away because of its grandiose 12th-century fortress. Previously a major rest station on the Via Francigena pilgrimage route, the village boasts centuries of intriguing stories, with the most prominent one being the one about Ghino di Tacco, a local Robin Hood who subsequently earned the forgiveness of the Pope.
While here, you can stroll the flower-covered lanes, go to the Romanesque Church San Pietro, and enjoy the panoramic views that stretch to the Tuscan land. Radicofani can be combined with a Val d’Orcia trip (with other beautiful towns in Tuscany like Pienza or Bagno Vignoni being nearby).
Where to stay: For exploring the countryside, you can use La Locanda del Postino, Podere San Giorgio, or Agriturismo Selvella as bases for exploring this part of rural Tuscany.
Chiusdino
Chiusdino is a picturesque, traditional medieval village, hidden in the Metalliferous Hills of southwest Siena. It’s famous for being the birthplace of Saint Galgano, the knight who famously plunged his sword into a stone—a story that inspired the legend of Excalibur. The Abbey of San Galgano, almost adjacent, is a ruin, roofless, but one of the most famous ruins in Tuscany. Take walks through the streets with a small path with flowerpots and laundry-covered windows, and enjoy a delicious local lunch at La Grotta di Tiburzi.
Where to stay: Agriturismo San Galgano, Palazzo a Merse, or La Fornace di San Galgano are wonderful country options.
San Quirico d’Orcia
Located between Pienza and Montalcino, San Quirico d’Orcia is a gem of the Val d’Orcia and home to some of the most iconic cypress-lined views of Tuscany. The town itself is very medieval- the Romanesque Collegiate Church of Saints Quirico and Giulitta, up to the well-maintained Horti Leonini gardens. Poggio Covili, the most photographed farmhouse in all of Italy, is just outside town, and the towns of Bagno Vignoni, Pienza, and Montalcino are also nearby, meaning San Quirico d’Orcia is one of the best bases to explore the scenic valley of Orcia.
Where to stay: Hotel Palazzo del Capitano, Agriturismo Il Rigo, or Casa Lemmi are all great places to stay in the town or nearby.
Suvereto
Suvereto is the so-called perfect Medieval hill town and is found in the province of Livorno, approximately 90 km southwest of Florence. It’s over 1000 years old (making it one of the oldest ones in the region), and its stone-arched and ivy-clad facades, as well as narrow alleys, are a photographer’s dream. Also, don’t miss out on Rocca Aldobrandesca, the Church of Madonna Sopra la Porta, and Pieve di San Giusto.
Olive groves, cork forests, and vineyards cover the town, and they yield quality wines and olive oil. And if you’re visiting in late autumn, the Sagra del Cinghiale (wild boar festival) in Suvereto, held in November, is one of the most popular local festivals.
Where to stay: Bulichella Wine Resort, La Fonte degli Angeli, or Agriturismo Le Piane are rustic, luxurious accommodations with local food and wine experiences.
Santa Fiora
It’s located on the southern side of Monte Amiata in the Maremma region, which is a mixture of medieval charm and gorgeous natural scenery. The town, which was formerly under the Aldobrandeschi and afterwards the Sforza family, still bears the splendour of the Palazzo Sforza Cesarini. The Museo delle Miniere di Mercurio informs visitors about the historical background of mining in the area, and the Pieve delle Sante Flora e Lucilla is known for its worldwide-famous Della Robbia ceramics. Santa Fiora may be combined with a trip to Pitigliano or the thermal baths of Saturnia.
Where to stay: Pieve Vecchia, or Agriturismo La Selvella provide comfortable accommodation with contact with nature.
Murlo
Murlo is an obscure treasure that lies in the vicinity of Siena, among the oldest Etruscan colonies of Tuscany. Poggio Civitate, an archeological site displaying remnants of the Etruscan civilization, and Vescovado, where the majority of the inhabitants are situated, make up the commune. Murlo is a charming city with a sense of calmness; stone houses, small playgrounds, and quiet walking paths have made Murlo a good place to be with the family.
Nighttime at this place is characterized by gelato walks and sunsets with hilly landscapes. It is also in a very good position as a setting to have day trips to Siena, Buonconvento, and the Val d’Orcia.
Where to stay: Villa Bosco, La Locanda del castello, or Agriturismo Casa al bosco is a good country hotel with a calming atmosphere.
Pienza
Pienza is situated in the centre of Val d’Orcia, and it is the so-called ideal city of the Renaissance. This UNESCO World Heritage site was built by Pope Pius II in the 15th century, and it’s one of the main highlights not just of the town but of the entire region. You can also visit the Cathedral of Santa Maria Assunta, the Palazzo Piccolomini, and the Piazza Pio II, a couple of the most exquisite of the Italian squares dotted with stalls of fine crafts and artisans that bring to life the magnificent sceneries of the Val d’Orcia.
Where to stay: La Bandita Townhouse, Relais Il Chiostro di Pienza, or Agriturismo Terrapile are three great options with a boutique look and glimpses of countryside and farm scenery.
Montepulciano
This hilltop town, between Pienza and Chiusi, is famous for its Vino Nobile di Montepulciano, one of the best preserved medieval gems in Tuscany. Head down the Corso Buozzi to the Piazza Grande, which is the location of the Cathedral of Santa Maria Assunta and a number of Renaissance palaces. Cantina Contucci and Podere Casanova Tasting are great experiences for wine lovers looking to get a taste of Tuscany’s most famous wines. Montepulciano also has spectacular vistas over the Val di Chiana and Val d’Orcia, and is a must-visit place in the south of Tuscany.
Where to stay: Agriturismo Il Fienile, Etruria Resort & Natural Spa, or Albergo Duomo to spend the night in a traditional Tuscan style.
San Gimignano
San Gimignano is nicknamed the town of Fine Towers, and it has one of the most iconic skylines in Tuscany. With more than 70 towers constructed by wealthy families, 14 of them still stand today, towering over the town’s medieval streets. A few of the city’s highlights feature the Collegiate Church of Santa Maria Assunta, frescoed by Ghirlandaio, and the Piazza della Cisterna, enclosed by stone palaces. Wine lovers must also visit the town as it’s home to a signature wine called Vernaccia di San Gimignano, and tasting it is one of Italy’s culinary highlights.
Places to stay: Hotel Leon Bianco, Il Casale del Cotone, or Agriturismo Niccolai -Palagetto di Sotto are all good places to stay with views of the vineyards.
Bagno Vignoni
Bagno Vignoni is a spa village like no other, situated in the heart of Val d’Orcia, approximately 5 km south of San Quirico d’Orcia. The main square consists of a large pool of stone topped by natural thermal springs. In the morning, warm mist is floating on the water, which creates a surreal and dreamy impression on the entire village. There are ancient baths where Saint Catherine of Siena used to bathe, and the Parco degli Mulini next to it boasts of old water mills hewn out of the rock.
Where to stay: Adler Spa Resort Thermae to enjoy luxury and wellness, Hotel Posta Marcucci to experience the traditional charm, and Locanda del Loggiato for a romantic getaway.
Lucca
Lucca is among the most beautiful cities in Tuscany, surrounded by intact Renaissance frameworks. One can walk or ride on the ramparts that are lined by trees and overlook the old center. In the interior, Lucca impresses the visitors with its Piazza dell’Anfiteatro, which was constructed on the foundations of one of the Roman amphitheatres, and with a great number of churches, which give Lucca the nickname “the town of 100 churches”. Take a tour to the top of Torre Guinigi, topped with ancient oak trees and views of the famous terracotta-covered rooftops.
Where to rest: Hotel Ilaria, Palazzo Dipinto, and Villa Romantica are all comfortable and within walking range of the old town.
Monteriggioni
Monteriggioni is one of the most beautiful medieval towns in Tuscany, and even today, it looks nearly the same as it did in the 13th century. The town is completely surrounded by a circular fortress, which was constructed by the Sienese to defend the town from Florentine attacks, and it has 14 watch towers and a single circle of stone walls that fully surround the town.
Inside, all the streets, piazzas, and trattorias are cobbled, and visitors can explore the Museum of Medieval Armory, one of the finest of its kind in the entire country. If you decide to visit in July, you can also attend the Medieval Festival, when the town is full of knights, minstrels, and market stalls, and everything looks so medieval.
Hotel to stay: Romantic Hotel Monteriggioni, Castel Pietraio, or Agriturismo Il Colombaio, all of which give a true glimpse into the town’s medieval tranquility.
Greve in Chianti
The town of Greve in Chianti is regarded as the entry point of the Chianti region and is a bustling wine town with vineyards and hills of cypresses covering it. It has its principal square, Piazza Matteotti, where there is a market on Sundays and some typical Tuscan charming cafes, wine stores, and one of the region’s most famous Wine Museums (Museo del Vino).
Trekking enthusiasts can take several different short walks uphill that lead to the nearby Castello di Montefioralle, which contains one of the best preserved medieval hamlets in all of Tuscany. Greve provides an ideal ground to tour the wine in such estates as Castello di Verrazzano or Viticchio.
Where to stay: Villa Bordoni, Castello di Verrazzano Agriturismo, or Alberto del Chianti are all great options to stay in classic comfort and views of the scenic vineyards.
Cortona
Cortona is a hill town in the ancient Etruscan Val di Chiana, which was popularized by the iconic novel Under the Tuscan Sun. Its pavements are made of cobblestone, which leads to beautiful piazzas, cafes, and breathtaking views. Go to Museo Diocesano with works of Fra Angelico, and to the Santa Margherita Sanctuary to have a panoramic view of the scenic rolling hills that inspired the bestselling novel. Cortona is swamped with cultural activities, including antique fairs and film festivals, and it’s also the perfect base to visit Lake Trasimeno or neighboring Montepulciano.
Where to stay: Relais Il Falconere and Spa.
Montefollonico
Montefollonico, situated between Pienza and Montepulciano, is often called the village of silence. This small medieval hamlet is enclosed by olive groves and vineyards, and it’s worth coming to when a person wants to find a tranquil place that feels genuine. Browse in its paving of stone through its alleys, to the Church of San Leonardo, or the grimy dungeons of its ancient ramparts.
One restaurant that should be visited by food lovers is La Botte Piena, which is a popular slow-food restaurant, offering one of the finest culinary experiences in Italy. Montefollonico is ideally matched with Pienza or Torrita di Siena, perfect for people wanting to spend some time in the countryside.
Where to stay: Relais La Costa or Podere Prasiano – small agroturisms with a lot of character, gorgeous views, and local food.
Volterra
Volterra is one of the most foreboding hill towns in Tuscany. Located high above the Cecina Valley, it’s a town famous for its Etruscan origins and alabaster craftsmanship. Stroll in the Piazza dei Priori, one of the oldest Italian medieval squares, and visit the Etruscan Museum Guarnacci, which is filled with old funeral urns. The Roman Theatre and Porta all’Arco are the ones that reveal the deep history of the town. The dark beauty of Volterra became the atmosphere of Twilight, but its ultimate magic is in the silence of the streets, in the artisan workshops.
Accommodation: Hotel La Locanda, Park Hotel le Fonti, or Agriturismo Podere are perfect options for visitors looking for a stay with a boutique feel, picturesque sceneries dotted with vineyards, and comfortable amenities.
Enjoying this post? Then you may also like our lists of hidden gems in Bologna and hidden gems in Verona.
Sorano
Sorano, a labyrinth of alleys, arches, and stairways seemingly carved out of stone, is located a few kilometers away from Pitigliano. The town’s skyline is dominated by the Fortezza Orsini and Masso Leopoldino, but Sorano isn’t just about cultural sites. It’s also home to natural hot springs at Terme di Sorano, which provide one of the most relaxing experiences in the region. Sorano is still relatively unfrequented, and there are fewer tourists around here; the place has a more local rhythm.
Where to stay: Residence Terme di Sorano or Agriturismo Biologic Farm La Selva are perfect options for people wanting to be close to most of the town’s highlights while also enjoying spectacular views of the rolling countryside.
Monterosso al Mare
Monterosso is the biggest of the Cinque Terre villages that blends the color of the seaside with the Tuscan hospitality. It’s divided into the old town and Fegena (the new beach part), which is why it is the best destination to visit for people who like both history and relaxation. You can visit the Church of San Giovanni Battista, the iconic Villa Montale, and taste anchovies – the local delicacy. The beach is a sandy one, unlike the Cinque Terre beaches, and the footpaths along the coast to Vernazza are one of the most picturesque walks in Italy.
Castiglione della Pescaia
Castiglione della Pescaia is a very pretty seaside town, with a perfect combination of beach life and a medieval atmosphere, located in the Maremma region of southern Tuscany. It’s an ancient town situated on a hill that has an old fortress on top, with turquoise waters and golden sands. There are restaurants that sell seafood in the marina, and close by, wetlands such as Diaccia Botrona are home to pink flamingos and herons. The town is a heaven for nature lovers and beachgoers and is often paired up with either Grosseto or Massa Marittima.
Massa Marittima
Last but not least, we conclude this list of the most picturesque towns in Tuscany, a very well-preserved secret of the region, located between Siena and the Tyrrhenian coast. The town is full of history and art, and some of its highlights feature the Cathedral of San Cerbone, the Palazzo Pretorio, and the Public Fountain with its impressive frescoes that illustrate the Piazza Garibaldi, one of the most beautiful medieval squares in Italy.
Having been a mining prosperity town, it now has an atmosphere of a quiet cultural retreat with wine ranches all around it. The Torre del Candeliere is a place not to be missed to have a panoramic view, and while you’re around, you can also visit Castiglione della Pescaia or Suvereto.
Where to stay: Hotel Il Sole, Casa Guaitoli, or Agriturismo Podere La Fornace are all perfect options for those who seek a taste of the true Tuscan experience.
How did you like this list of picturesque towns in Tuscany? Did you ever visit any of them? Feel free to share your thoughts and experiences in the comments below.
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