The cities of Tuscany—Florence, Pisa, and Siena—are well-known for their iconic attractions such as the Uffizi Gallery, the Leaning Tower, and the Piazza del Campo. However, this beautiful region is also home to numerous smaller towns that make perfect destinations for a villa holiday in Tuscany. These quaint Tuscan towns are hidden treasures, ideal for escaping the tourist crowds and experiencing an authentic slice of Italy. Here are our top 10 towns to consider for your Tuscany villa getaway.
Volterra
Located just two hours from the bustling streets of Florence, the serene hilltop town of Volterra offers a peaceful escape. Known for its rich and ancient history, Volterra ranks high on our list of Tuscany villa destinations. Its Etruscan heritage is showcased through various artifacts in the local museum, while remnants of its Roman past can be seen in the first-century Roman amphitheater, forum, and baths. Additionally, Volterra has a long-standing reputation for its alabaster craft, and visitors can explore numerous workshops that continue to operate today.
Monteriggioni
Monteriggioni is a picturesque hilltop town with historic towers visible from miles away. Believed to date back to the 8th century BC, the town’s castle was constructed by the Sienese in the 13th century for defense against the Florentines. Monteriggioni is remarkably well-preserved, giving visitors the feeling that time has stood still. For an immersive experience, plan your visit during the Medieval Festival of Monteriggioni in July, where you’ll witness residents dressed in period costumes and enjoy traditional medieval dishes.
San Gimignano
San Gimignano, famous for its 14 medieval towers, draws an impressive 2.5 million visitors each year. Visitors can only ascend the Torre Grossa, but the effort is well worth it for the stunning views over the Val d’Elsa. Although only a fraction of the original 72 towers remain, San Gimignano is still a remarkable example of medieval Tuscan architecture, filled with charm and beauty.
Pienza
Pienza, a UNESCO World Heritage site, is a small yet stunning village in Tuscany, exemplifying Renaissance beauty. Designed by architect Bernardo Rossellino under Pope Pius II, Pienza’s piazzas and palazzos reflect humanist ideals. This serene town is considered one of the most romantic in Tuscany, featuring the charming Via dell’Amore (Street of Love) and Via del Bacio (Street of the Kiss). It’s no wonder that it served as a filming location for Franco Zeffirelli’s adaptation of Romeo and Juliet.
Cortona
Cortona gained fame through Frances Mayes’ book ‘Under the Tuscan Sun’. While its history traces back to the Etruscan era, the town is characterized by its medieval architecture. Perched 600 meters above sea level, visitors can enjoy breathtaking panoramic views of the Valdichiana and glimpses of Lake Trasimeno in nearby Umbria. For the best views, visit the Santa Margherita Sanctuary and the Girifalco Fortress.
Montepulciano
Montepulciano is a stunning town brimming with captivating churches, beautiful palaces, and charming piazzas. With many pedestrian-only streets, exploring the town is a delightful experience. The heart of Montepulciano is the Piazza Grande, home to both the Palazzo Comunale and the Cathedral. Additionally, this town is renowned for producing Vino Nobile, one of Tuscany’s premier wines, making it a must-visit for wine lovers.
Anghiari
Anghiari is an enchanting medieval village encircled by sturdy 13th-century stone walls. It ranks among the 29 borghi piu belli d’Italia in Tuscany, a collection of towns admired for their historical and artistic significance. The village’s narrow streets are lined with charming houses, shops, and churches adorned with colorful window boxes that overflow with flowers. Anghiari is historically notable for the 15th-century Battle of Anghiari, where the outnumbered Florentine forces triumphed over Milan on June 29, 1440. This event was immortalized by Leonardo da Vinci in a lost painting, but the village’s museum offers insights into this fascinating history.
Lucca
Often cited as a favorite among our list of Tuscan towns for a villa holiday, Lucca captivates visitors with its well-preserved city walls, perfect for walking or cycling. Nicknamed ‘the city of one hundred churches,’ Lucca boasts a wealth of religious buildings, owing to its historical significance as a key stop on the pilgrimage route of Via Francigena. Among its highlights are the oval-shaped Piazza dell’Anfiteatro and the Torre Giunigi, a tower with trees flourishing in its rooftop garden, symbolizing the town’s rejuvenation.
Pistoia
Pistoia, located midway between Florence and Lucca, may not have the grandeur of its famous neighbor but offers a rich historical backdrop for visitors. With roots traceable to Roman times, Pistoia boasts notable attractions such as the Piazza del Duomo, home to the Cattedrale di San Zeno (Duomo), the Medieval Baptistery, and a striking marble-striped church, San Giovanni Fuorcivitas. There’s plenty to explore beyond these sites, making it a worthwhile base for a Tuscany villa holiday.
Cetona
Last on our list of top towns for a Tuscany villa holiday is Cetona, a delightful medieval town centered around the charming Piazza Garibaldi and dominated by a 10th-century fortress surrounded by lush pine and cypress trees. Like many Tuscan hill towns, Cetona offers splendid views of the surrounding countryside, with even better vistas from nearby Monte Cetona, peaking at 1148 meters. On clear days, you can see as far as Perugia and Assisi. Visit during spring for the Cetona in Fiore festival, where the town blooms with flowers, or in July for the lively La Corsa delle Brocche event.
