Tuscany’s famed landscape combines pastoral scenes with rustic farms and cypress-lined drives with the historical splendor of cities like Florence, Siena, and Pisa. For a family vacation with a difference, rent a villa in one of these hidden gem towns.
Streamlined interiors and stylish accent furniture merge with ancient stone walls and beamed ceilings. Fourteen years of restoration brought this charming Tuscan villa to its former glory.
Pienza
The perfect Tuscan getaway is not hard to find. You just need to know where to look! This enchanting region is best known for its sweeping landscape of rolling hills dotted with olive groves and vineyards but hidden gems such as Val d’Orcia and Monticchiello offer a much more cultural experience. The latter is home to a perfectly preserved 13th-century church as well as some of the area’s finest cheeses and wine and was chosen as the backdrop for Gladiator, where the film crew recreated Rome’s Elysian Fields complete with ribbony roads of cypress trees.
The heart of this stunning region lies in the quaint hilltop village of Pienza. A UNESCO World Heritage Site, the city was designed on the ideals of Renaissance idealism by architect Rossellino and is considered to be one of the ‘ideal cities’. It is also the capital of Italy’s famed pecorino cheese which has its origins here in the high pastures of the Val d’Orcia.
Pienza’s awe inspiring architecture and idyllic setting make it a popular choice for painters, photographers and film directors. The city was immortalized in Franco Zeffirelli’s 1968 version of Romeo and Juliet with Leonard Whiting and Olivia Hussey as the star-crossed lovers. The city’s awe inspiring buildings and magical atmosphere made it the perfect setting for this story of true love.
Among the most famous sites in Pienza is Palazzo Piccolomini, designed by Rossellino and home to important antique furniture, works of art, a prized library and special relics. The roof garden offers a breathtaking panorama of the valley surrounding the city.
Another must-see is the imposing Duomo cathedral which stands majestically over the city’s main square. The palazzo, the cathedral and the town hall are all adorned with impressive frescos by famous Italian painters such as Giotto, Titian and Veronese.
Pienza is a delightful place to visit all year round. It is quieter in winter when most restaurants and shops are closed but even during peak season (May to September) it never feels overcrowded. For a truly unique experience try visiting in January or February when the entire village is deserted – it almost feels as though the locals have escaped and are hibernating!
Montalcino
A dreamy paradise of dazzling medieval architecture and world-famous wines, Montalcino is one of Tuscany’s most charming hill towns. It’s a place of magical 14th-century fortresses, abbeys, and bustling town centers with all sorts of fantastic events going on throughout the year. It’s also home to some of the most acclaimed red wines in Italy, including the feisty Brunello di Montalcino.
With a backdrop of sweeping green hills, lush vineyards and olive orchards, a stay at a villa in this beautiful region is a once-in-a-lifetime experience. Whether it’s during the early morning as the mist rises above the vineyards or at sunset as the sun sinks below the horizon, the scenery here is simply mesmerizing.
In addition to the incredible wines, the cuisine here is truly worth your while. There are plenty of restaurants in Montalcino where you can enjoy lunch or dinner with a view, allowing you to fully soak up the breathtaking landscapes.
Some of the best restaurants in Montalcino to enjoy a meal with a view include Drogheria e Locanda Franci and Taverna del Grappolo Blu. The former is a historic restaurant with an impressive view of the town, while the latter serves up traditional Tuscan dishes with a twist.
Another great option is Boccon DiVino. This family-run restaurant offers a variety of wine tastings as well as typical Tuscan specialties such as chianina steak tartare and platters of cheeses and cold cuts.
Lastly, if you’re looking for a unique experience in Montalcino, consider a cooking class at Locanda Demetra. The sisters who run this establishment are incredibly passionate about Tuscan culinary traditions and will teach you all the secrets to creating your own amazing Tuscan meals.
When it comes to staying in a villa in Montalcino, there are many wonderful options to choose from. However, there is one particular Tuscan villa that stands out above the rest. Villa San Sigismondo is an elegant Italian villa with private pool that’s located just 9 kilometers from Montalcino, an enchanting little town known all over the world for its world-class wines. This stunning Tuscan villa is the perfect place to relax and unwind. The villa has been furnished with extreme taste, combining modern elements with ancient wood beam ceilings – and as such, seeking out a rent villa in tuscany becomes an absolute must.
Arezzo
Despite the fact that it’s often missed off Tuscany’s main itineraries, Arezzo is a treasure trove for art and history lovers. Founded as an Etruscan city, the old town’s narrow streets are a delight to wander. The imposing Arezzo Cathedral has painted vaulted ceilings, and the Basilica di San Francesco contains a 15th-century fresco of Mary Magdalene by Piero della Francesca.
For more Renaissance art, head to the Museo di Arte Medievale e Moderna, which brings together major paintings and sculptures from the era of Giorgio Vasari, who was born here. The museum’s collections are housed in the Casa Vasari, a palazzo decorated by the artist himself.
The city center is a pedestrian zone, and the main square (Piazza Grande) is filled with towers, churches and palazzi. It’s the setting for the famous Saracen jousting reenactments held twice a year. You can also watch local artisans at work in the artisan shops that line the square. The family-run Busatti textiles workshop, for example, weaves fabric on ancient shuttle looms with Florentine Renaissance motifs, and sells everything from tablecloths to napkins and tea towels.
Arezzo is a bargain hunter’s paradise and one of the best places in Italy to browse antiques. The first Sunday and Saturday of each month the renowned Arezzo Antiques Fair fills the main square and its surrounding streets with over 500 stalls. Roman coins, ornate grandfather clocks and china are among the items for sale.
Wine lovers should book a tour and tasting at Buccia Nera, a 50-hectare winery that uses organic and sustainable farming methods to produce a variety of wines from both indigenous grapes and international varieties. A sommelier will guide you through the estate’s different types of wine, including the flagship “Pianello”, and you can sample some of their signature vintages in the tasting room.
Arezzo is a great base for day trips to Cortona and other nearby historic towns. You can see the main sites in a half-day, but for a more relaxed pace it’s recommended to spend a full day here. Then you’ll have time to stop for a leisurely lunch, a glass of wine at a restaurant, and visit some of the city’s museums and art galleries.
San Gimignano
The UNESCO-listed hilltop town of San Gimignano is instantly recognizable by its iconic towers. It’s a fascinating time capsule of medieval Tuscany that evokes gasps from visitors the moment they step into its ancient walls.
This enchanting little town is a popular Tuscan tourist attraction, which means that it can get pretty crowded during the summer months. The best way to avoid this is to visit in the fall or spring when the weather is still warm but not as stifling.
As a result, there are more places to explore and fewer people to jostle for space. If you’re lucky enough to be in the area for a couple of days, try to arrive at sunset so that you can see the town’s streets bathed in soft orange light.
A walk through the paved alleyways and quaint buildings of San Gimignano’s historic center is a magical experience. It’s also one of the best ways to learn more about the city’s long and fascinating history. There are a variety of architectural gems here that reveal how the town evolved over the centuries from Etruscan roots through the Middle Ages and then into the Renaissance, as evidenced by the numerous works of art in the Collegiata and Sant’Agostino churches and the Communal Palace.
San Gimignano’s medieval time-capsule has provided a striking backdrop for countless movies and television shows. Several scenes from the TV series The Medici: Masters of Florence were filmed here, as were some of the romantic period dramas A Room with a View and Under the Tuscan Sun. Franco Zeffirelli used the town as a stand-in for Assisi in his 1972 Saint Francis of Assisi biopic Brother Sun, Sister Moon.
Whether you’re looking for an inspiration for your next novel or just a place to recharge and reconnect with the world, San Gimignano is an ideal escape from the hectic pace of modern life. It’s also a great spot to indulge in Tuscan cuisine and wine, which is why many villa guests make this charming town their home base for several days or more.
