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Six Marvelous Medieval Places in Tuscany

Tuscany is without a doubt one of the world’s top destinations for dream vacations and weddings. No matter where your interests lie — art, architecture, history, nature, food, wine, fashion, shopping — Tuscany has it all. Situated just under the “knee” on the “boot” of the Italian mainland, the region is one of the most visited in the country. Tuscany’s port of Livorno is a frequent stop on Mediterranean cruise routes.

Famous for its beautiful capital city, Florence, and its many respected wine regions, Tuscany is also loaded with amazing Medieval places, those hilltop villages you see on postcards, set amongst rolling terrain and fields of sunflowers.

Although the sunflowers are sleeping now, the drizzly days and cloudy skies of winter present a unique atmosphere in which to visit Italy, where the rain and gloom serve only to enhance the dramatic nature of its Medieval sites. With this post, we begin a series on Italy’s Medieval places by shining the spotlight on six marvelous villages in Tuscany.

Trying to narrow down all the wondrous Medieval places in Tuscany to a short list is a tall order! The author willingly confesses that the places presented here represent only a few personal favourites after living and traveling extensively in Tuscany for more than twelve years.


For Medieval marvels on a grand scale, you can’t beat Siena. In the winding stone streets, you are surrounded by that intimate aesthetic of centuries gone by, but then you turn a corner to be greeted by sheer grandeur at several unforgettable points, namely Piazza del CampoPiazza del Duomo, and the Basilica of San Domenico. (When you consider that Siena only has about 50,000 inhabitants, the majesty of these monuments is pretty mind-boggling.)

Piazza del Campo is Siena’s main square, a wide-open, handsome plaza in the shape of a fan. It is in this piazza that the world’s craziest horse race, the Palio di Siena, takes place each summer.

The two massive churches that define Siena’s cityscape sit at opposite ends of the architectural spectrum. The Duomo (cathedral) rises like a cheery, striped bon-bon of black and white marble with a glittering facade, while the Basilica of San Domenico casts a somber but elegant figure with its simple brick exterior. Inside the basilica are treasured relics (the head and thumb) of Santa Caterina, Siena’s patron saint.

In addition to this architectural eye candy, Siena is brimming with gorgeous boutiques featuring artisan leather goods, high-quality clothing, and the city’s iconic sweet treats.


Now onto mid-size Medieval places: San Gimignano and Volterra.

San Gimignano is one of those Medieval places in Tuscany that has achieved superstar status. With its numerous Medieval towers, it has rightfully earned the nickname “The Manhattan of Tuscany”. Wandering through San Gimignano, you feel immersed in a fairy tale. If you meander up to the fortress, breathtaking views await you. If you love to shop, you may very well exhaust your life savings. If you have a sweet tooth, you can indulge (or maybe overindulge) in award-winning gelato while enjoying the fine figure of the ancient well that adorns the main piazza.

Located seventy-five minutes from the port of Livorno, Volterra is the most convenient Medieval destination from Tuscany’s principal port. Volterra is a magical place — perhaps in both figurative and literal senses. Volterra, like San Gimignano, was established by the Etruscans, the ancient and advanced civilization that inhabited central Italy between the 8th and 3rd Centuries BCE. The Etruscans had a knack for discovering locations (usually on hilltops) with special energetic properties, a phenomenon that has been the subject of some study in recent years. Like San Gimignano, the panoramic vistas of the Tuscan landscape that you get in Volterra are an incredible thing, and the distinctive architectural points of interest will have you snapping a zillion photos.

VILLAGES IN CHIANTI: Montefioralle, Castellina, and Volpaia

There are enough charming villages in Tuscany to fill an entire guidebook, but no list of marvelous Medieval places would be complete without mentioning villages in Chianti. In Italian, a village is called a borgo, but a borgo is smaller than a village, more like a hamlet. If you see a village designated as one of the “borghi più belli d’Italia” (most beautiful villages in Italy), you’ll want to stop and tarry a while. Over three hundred hamlets in Italy have been granted this title by an association established in 2001 to promote “the great historic, artistic and cultural heritage of the Italian small centers.”

On the list of I Borghi Più Belli d’Italia is Montefioralle. Sitting on a ridge of the Chianti hills, this cluster of stone and brick houses is still encircled by its original fortification walls. According to legend, Leonardo da Vinci painted the Mona Lisa nearby, with the rolling Chianti countryside as the backdrop.

Not on the list of I Borghi Più Belli d’Italia, surprisingly, are two villages that this writer adores: Castellina in Chianti and Volpaia. Located a bit past the halfway point between Florence and Siena, these hamlets are absolute gems. Not only does Castellina have a castle — the Rocca — dating back to the 15th Century, it also sports an unusual feature: the Via delle Volte, a sort of fortified underground gallery that you can still stroll through. You can also find good, genuine Tuscan cooking in a variety of trattorie (casual eateries) in Castellina, and the overall scene is pretty lively. Volpaia, on the other hand, is decidedly quieter, but its stone buildings and lush setting are the stuff of photographers’ fantasies.

If Italy’s marvelous Medieval places are beckoning you, let DriverInRome escort you on a magical journey of discovery! Please contact us to learn about all destinations, whether you are arriving by cruise ship or staying in Rome, Tuscany, or Sicily.

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