Located in the northern region of Italy, Tuscany is a world-renowned destination for great food, history, and architecture. Travelling within this region is like taking a step back in time when cobbled streets and city walls were part of daily life. You can see medieval-era castles, sample some of the best wines in the world, and even cheese made from sheep milk.

    From modern cities like Florence and Pisa to the medieval towns of Montepulciano, Volterra, and Cortona, check out our guide of beautiful towns you must visit in Tuscany – many of them are just a bus ride away from Italy's larger cities.



    Home to some of Italy's renowned monuments

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    Florence is the capital of the Tuscany region, renowned for its historic contribution to Italian culture, fashion and architecture. Notable sights include the fountain of Neptune and Galleria dell'Accademia, which is home to Michelangelo's David sculpture. Rows of shops and stalls span the length of the Arno River, which is highlighted by the centuries-old Ponte Vecchio Bridge.

    This city centre is dominated by Cathedral of Santa Maria del Fiore (or Duomo), which has a 15th-century terracotta dome designed by Filippo Brunelleschi. Step inside to see Giorgio Vasari's frescoes of the Last Judgment – entrance is free of charge.

    Location: Florence, Firenze, Metropolitan City of Florence, Italy



    Known throughout the world for its iconic leaning tower

    Pisa is a prominent town within the Tuscany region. Home to interesting museums, botanical gardens, and spectacular scenery, it's no wonder why thousands of travellers make their way to this town every year. The leaning tower is part of a larger complex called Piazza di Miracoli, which contains the Cattedrale di Pisa. This Romanesque cathedral houses many important relics, including the mummified remains of San Ranieri, the patron of Pisa.

    The Old Town of Pisa is a particularly charming part of town. A must-visit for shoppers is the Borgo Stretto pedestrian zone, where you can find trendy bars, fashion boutiques, and pastry shops.

    Location: Pisa, Province of Pisa, Italy



    A Tuscany town on the Serchio River

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    The small Tuscan town of Lucca is encircled by well-preserved Renaissance walls that date back to the 16th century. The old city walls span 4 km in length, which you can explore on foot or bicycle. The panoramic walkway overlooks the entire town.

    Known as "the city of 100 churches", some of its most popular cathedrals are San Michele al Foro, San Martino, and San Frediano Basilica. Other notable sights such as the Torre delle Ore, Guinigi Tower, the Museum of Villa Mansi, and the Piazza dell'Anfiteatro amphitheatre.

    Location: Lucca, 55100 Province of Lucca, Italy



    Its town square hosts a horseracing event every July and August

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    Siena is a UNESCO World Heritage Site in the southern part of Tuscany. Known for its terracotta roofs and narrow cobbled streets, the historic old town is home to the Cathedral of Siena, Palazzo Pubblico, Palazzo Salimbeni, and the enormous Basilica of San Domenico. There are plenty of museums that'll take you back to the Renaissance days through compressive exhibits, along with picturesque courtyards that offer nice spots for picnics.

    Twice a year, usually July and August, the town's Piazza del Campo square becomes a racetrack for Palio di Siena, a historical horseracing event that dates back to medieval times, Siena is relatively small, making it easy to explore its historical sites within a day.

    Location: Siena, 53100 Province of Siena, Italy



    One of the smallest towns in the Tuscany region

    Montepulciano is a medieval hilltop town surrounded by vineyards. It's known for its exquisite regional cuisine and Vino Nobile, a red wine primarily made from the Sangiovese grape. Most restaurants serve local Tuscan dishes, including pork and cheese, as well as a type of thick pasta called pici. They're often paired with the town's local wines. 

    Montepulciano has 1 main street, which stretches from Porta Al Prato to Piazza Grande. You can get to this quaint town by bus from Florence, Rome, and Siena.

    Location: Montepulciano, 53045 Province of Siena, Italy



    A mountaintop town southwest of Florence

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    Volterra lies around 80 km southwest of Florence. If you're staying in Siena or San Gimignano, you can visit this mountaintop town as a day trip – both are about an hour-long drive away. The town is small enough to explore on foot. Its main plaza (or central piazza) is a bustling square lined with medieval alleyways, marbled buildings, bell towers, and ancient Roman theatres.

    Spend the day visiting Porta all'Arco (the oldest gate in the city), an Etruscan acropolis dating back to the 2nd century BC, the town's Roman amphitheatre, and surrounding archaeological areas. You'll also find 2 castles dating back to the 13th century. The Palazzo dei Priori and Palazzo Pretorio tower over the square, and can be toured for a few euros.

    Location: Volterra, 56048 Province of Pisa, Italy


    San Gimignano

    Ancient city under the Tuscan sun

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    A series of bell towers and buttresses rise over the medieval houses at the ancient hilltop town of San Gimignano in Tuscany. Soak up the vibes of this enchanting city from its triangular piazza, the bustling Piazza della Cisterna (named after a cistern or well that has served as the town’s centrepiece for centuries).

    From here, you can check out some of the important landmarks built by the Knights of Malta, and roam the narrow streets lined with local vendors showcasing their best ornate porcelainware and ceramics.

    Location: Siena, Italy

    Price: 713841



    Italy's "Little Jerusalem"

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    Set on top of a stony cliff in Italy’s Tuscany region, the medieval town of Pitigliano is an amazing sight. Most of its buildings and towers were built using the same rock from the cliff. Pitigliano has a longstanding Jewish community, and among its main sights are a series of ancient caves carved into the cliffside, once believed to have served as reclusive synagogues during the times of Roman persecution. Check out the former Cathedral of Santi Pietro e Paolo, as well as the medieval Orsini Fortress.

    Location: Pitigliano, 58017 Province of Grosseto Italy


    Castiglione della Pescaia

    Home to the Diaccia Botrona nature reserve

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    Castiglione della Pescaia is a coastal town with sweeping views of the Tyrrhenian Sea. Located between blue seas and green hills, this quaint village has ancient walls, towers, and even a 15th-century castle.

    The Diaccia Botrona nature reserve is one of the most important wetlands in Italy. The trails are popular for long hikes, bike rides, and horseback tours overlooking the ocean. Castiglione della Pescaia is often overlooked by touristy crowds, which makes for a very relaxing getaway in Tuscany.

    Location: Castiglione della Pescaia, 58043 Province of Grosseto, Italy



    A fortified medieval town

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    Monteriggioni is a medieval town home to one of the best-preserved wall castles in Tuscany. A short drive from Siena, Monteriggioni is made up of towering watchtowers, cobbled streets, and a busy town square. The town is located on top of a hill – enter through the Franca or Romea gates, which will take you to the town's main Piazza di Roma. 

    The Medieval Festival of Monteriggioni takes every July. One of the most popular festivals in Tuscany, the streets are packed with people in medieval costumes performing falconry displays and enjoying typical Roman dishes.

    Location: Monteriggioni, 53035 Province of Siena, Italy



    A UNESCO World Heritage Site since 1996

    Pienza is a world-renowned ‘Renaissance utopia' in Tuscany. This tiny village oozes refined and sophisticated architecture and is surrounded by the rolling hills of Val d'Orcia. Just 15 km from Montepulciano, Pienza is known throughout Italy for its sheep milk cheese. Many of the local dishes include this delicacy, which ranges from a delicate flavour to a more pungent one, based on how aged it is.

    The Cattedrale dell'Assunta in Pienza is home to paintings by some of the most renowned artists of the Renaissance. Other must-see spots include the Cathedral of Santa Maria Assunta, Palazzo Piccolomini, and Palazzo Borgia.

    Location: Pienza, 53026 Province of Siena, Italy



    Visit museums showcasing the town's Etruscan past

    Cortona is a small hilltop town with spectacular views of the surrounding valley and Lake Trasimeno. The Etruscan Academy Museum is located here, which displays a vast collection of bronze and ceramic items reflecting the town's Etruscan past. The museum also includes an Archaeological Park that has sections of old Roman roads. The Diocesan Museum is one of the best places in Tuscany to see sacred furnishings and paintings by the famous artist Fra Angelico.

    Cortona is known throughout the region for its great food and ample wine selections. Some of the world's best red wines are produced by wineries close to the town. Various small shops on the main streets of Cortona also offer local handmade items, which make great souvenirs.

    Location: Cortona, 52044 Province of Arezzo, Italy

    Fiorella Bertola | Contributing Writer

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