10 Towns for a Tuscany Villa Holiday

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Tuscany’s cities – Florence, Pisa, and Siena – need no introduction. They are famous the world over for attractions such as the Uffizi Gallery, the Leaning Tower, and the Piazza del Campo. However, the region is also bursting with several smaller towns, perfect for a Tuscany villa holiday. These smaller Tuscan towns can be real gems, places where you can escape the crowds and find an authentic slice of Italy to enjoy. Here are our favorite 10 towns for a Tuscany villa holiday.



Just two hours from the crowded streets of Florence sits the much quieter walled hilltop town of Volterra. Volterra’s long and ancient history ensures that it tops our list of 10 towns for a Tuscany villa holiday. Evidence of its Etruscan roots is apparent in the numerous artifacts that can be found in the town’s museum. Its Roman past is very much visible in the remains of the 1st-century Roman amphitheater as well as its Roman forum and Roman baths. This hilltop Tuscan town has also long been famous for its alabaster industry. A stroll through Volterra’s streets will allow visitors to discover the many alabaster workshops still present today. 


Monteriggioni forms a perfect circle atop a hill with historic towers that can be seen for miles around. It is widely believed that its origins date as far back as the 8th century BC. However, its castle was originally built by the Sienese for defensive purposes against the Florentines in the 13th century. Monteriggioni is arguably the most incredibly well-preserved town in our list of top 10 towns for a Tuscany villa holiday. Certainly, it almost feels like time has stood still when visiting Monteriggioni. If you can, try and time your visit with the Medieval Festival of Monteriggioni which takes place every July. At this time, you’ll enjoy a real glimpse into what life used to be like. The streets will be filled with residents dressed in Medieval garb whilst local restaurants will serve up dishes dating back to Medieval times. 

San Gimignano

San Gimignano is probably the most famous and well-known in our list of top 10 towns for a Tuscany villa holiday. Certainly, the 14 towers which dominate the skyline attract an estimated 2.5 million visitors each year.  Many are perhaps surprised to learn that the only tower visitors can climb up is the Torre Grossa. It’s certainly worth making the effort to do so though. The incredible vista over the Val d’Elsa that it enjoys from the top is impressive. These days you will have to use your imagination to picture how San Gimignano would have looked when all 72 original towers were standing. However, even though so many towers have not stood the test of time, San Gimignano remains a superb example of a Medieval Tuscan town, filled with incredible atmosphere and beauty. 


One of Italy’s many UNESCO World Heritage sites, Pienza is a small but incredibly beautiful village in Tuscany. Its beauty owes much to its 15th-century Renaissance Utopian beginnings. Under the watchful eye of Pope Pius II, architect Bernaro Rossellino organized all the piazzas and palazzi within Pienza according to humanist principles.  We also think that Pienza is the most romantic of our top 10 towns for a Tuscany villa holiday. Franco Zeffirelli certainly agreed with us. He used the Palazzo Borgia and the Palazzo Piccolomini in Pienza as the setting for his film Romeo and Juliet. And Pienza’s streets just add to the romance. The town is home to the Via dell Amore (Street of Love) and the Via dell Bacio (Street of the Kiss)!


Cortona became famous almost overnight thanks to Frances Mayes’ book ‘Under the Tuscan Sun’. Whilst Cortona’s history also dates as far back as the Etruscan period, what visitors see today dates back to Medieval times. Its narrow, cobbled streets sit 600 meters above sea level. This elevated hilltop setting means visitors will arguably fall in love as much with the views from Cortona as with Cortona itself. From the town, you can enjoy a panoramic view of the whole of the Valdichiana. These views include glimpses of Lake Trasimeno in neighboring Umbria. Head to the Santa Margherita Sanctuary and the Girifalco Fortress to enjoy the best views.


Montepulciano is incredibly pretty. Packed full of interesting churches and beautiful palaces, idyllic piazzas, and picturesque alleyways, most of its streets are free from cars, making it even more enjoyable to explore. The Piazza Grande, home to the Palazzo Comunale and the Cathedral sits at the heart of this Tuscan town. But the reason many would choose to stay in Montepulciano for their Tuscany villa holiday is as much to do with the produce that it’s home to as the town itself. The famous Vino Nobile is one of the top wines of Tuscany and the town is certainly the most important agricultural center in the area for viticulture. 


Anghiari is a charming Medieval village surrounded by thick 13th-century stone walls. It’s also one of 29 borgi piu belli d’Italia in Tuscany. This is a group of small Italian towns chosen for their strong historical and artistic interest. It well deserves the title. Anghiari’s narrow streets are charming. Lined with houses, shops, and churches, window boxes are filled with colorful flowers that seem to constantly cascade over the walls below. Historically, Anghiari is most famous for being the site of the famous 15th-century Battle of Anghiari. This is when, on 29 June 1440, the outnumbered forces from Florence defeated their opponents from Milan against all odds. These events were subsequently captured by Leonardo da Vinci in the Salone dei Cinquecento in the Palazzo Vecchio in Florence. Sadly, the painting has since been lost. But Anghiari’s museum is a great place to visit if you want to learn more. 


Possibly the favorite of our list of top 10 towns for a Tuscany villa holiday, Lucca’s principal attraction for many visitors is the old city walls. Here visitors can enjoy a stroll or cycle. However, Lucca is equally famous for its many churches. The town has certainly earned itself the nickname ‘the city of one hundred churches.’ Lucca is home to so many religious buildings because the town was once a key stopover on the pilgrimage route of Via Francigena. For us though, it’s the oval-shaped central Piazza dell’ Anfiteatro and Torre Giunigi that are the biggest attraction. The latter is a tower with trees growing from the roof garden at its summit. Built by the Guinigi family it is a symbol of Lucca’s rebirth. 


Pistoia is situated halfway between Florence and Lucca. There is no disputing that it’s no way near as grand as its more famous neighbor Florence. Plus, it’s just half the size of Lucca. Nevertheless, Pistoia is home to all the ingredients that make up a good base for a Tuscany villa holiday. With an illustrious history stretching back to Roman times, there is much to see and do in Pistoia. The Piazza del Duomo and the smaller Piazza della Sala are home to the Cattedrale di San Zeno (Duomo), Medieval Baptistry, and bell tower. Not to mention the Church of San Giovanni Fuorcivitas. The latter has a rather striking dark green and white marble-striped exterior. But there are numerous other sites in Pistoia also worthy of a visit too.


Last but not least on our list of the top 10 towns for a Tuscany villa holiday is Cetona.  A charming Medieval town, Cetona is centered around the Piazza Garibaldi and dominated by its 10th-century fortress (rocca) which sits above it surrounded by pine and cypress trees. As with so many of Tuscany’s hilltop towns, Cetona is also a great place to enjoy some fantastic views over the surrounding countryside. Although the views are even better from nearby Monte Cetona. Its summit is 1148 meters above sea level and from here, on a clear day, you can see as far as Perugia and Assisi. Visit Cetona in the Spring to take part in the Cetona in Fiore festival when the town will be filled with flowers. Or visit in July to enjoy the spectacle of La Corsa delle Brocche.

10 Towns for a Tuscany Villa Holiday

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