There’s no doubt that Florence is the cultural capital of Tuscany. Touted as the birthplace of the Italian Renaissance, this elegant city’s exquisite art, breathtaking architecture, and delicious cuisine capture the hearts of travelers. But if Florence is the beating heart of Tuscany, then the hill towns are its life blood. Steeped in centuries-old agricultural, viticultural, and artisan traditions, these sometimes-unassuming hamlets hold intriguing secrets just waiting to be discovered.
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Top 5 Tuscan Hill Towns
Travel through the pastoral hills of Tuscany to discover these five idyllic villages that will delight and inspire you with rich history, elegant wines, and countryside charm.
Radda in Chianti
Radda in Chianti (Volpaia): One of the most captivating small towns in Tuscany, Radda in Chianti has picture-perfect moments around every corner. From arched stone doorways and overflowing flower boxes to its statuesque bell tower and 13th-century church, Radda is a delightful way to spend a couple of hours. Continue up the road to an even smaller village, Volpaia. With a small cafe, winding pedestrian alleys, and views that never end, Volpaia is the perfect pairing with Radda.
Montalcino
Often confused with its larger neighbor Montepulciano, this delightful hill town offers a more intimate, laid-back experience. After pulling yourself away from the stunning Val d’Orcia views of verdant hills and patchwork valleys, take time to meander through narrow streets, discover artisan shops, and appreciate the historic architecture. Wine lovers can savor the town’s famous reds, Rosso di Montalcino and Brunello di Montalcino, at nearby wineries or any of the friendly cafes in town.
Cortona
One of the better-known Tuscan towns, Cortona’s sophistication and creativity are on display at every turn. History-lovers delve into the region’s past at the Accademia Etrusca, while art lovers can get their fix at the Diocesan Museum and the exceptional 15th-century cathedral. This vibrant, mid-size hill town has plenty of choices for food and drink, plus some viable creative shopping options.
Pienza
Panoramic views over the Val d’Orcia welcome you as you reach Pienza. A UNESCO World Heritage Site, this quaint hill town was home to Pope Pius II, who built the impressive Palazzo Piccolomini as his summer residence. The Pope’s love for beauty and architecture is reflected everywhere in Pienza. Small alleys beckon you to explore as they open up to small piazzas with outdoor cafes and blossoming vines.
San Gimignano
About an hour southwest of Florence and another UNESCO World Heritage Site, San Gimignano is known for its towers dating back as far as the 11th century. Originally home to 72 of these soaring stone structures, an impressive 14 remain. The towers historically served as lookouts for the walled city, but now, travelers tackle the 218 steps inside the town’s highest tower, the Torre Grassa, to marvel at spectacular Tuscan views. Other must-sees include the Cathedral and its beautiful frescoes, as well as strolling through the picturesque central palazzo.
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