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Three Hilltown Highlights of Tuscany

Tuscany is a well-known and well-loved parcel of landscape: with its near-desert aridity and rich, hot pine fragrance, the iconic countryside is interrupted by the occasional picturesque town, nestled...

Tuscany is a well-known and well-loved parcel of landscape: with its near-desert aridity and rich, hot pine fragrance, the iconic countryside is interrupted by the occasional picturesque town, nestled amongst the hills. These towns are frequently steeped in history, many being astonishingly well-preserved examples of medieval towns. Here we take a look at three unmissable medieval towns to incorporate into your tours of Tuscany.


Siena has a fair claim to the title of Italy’s most picture-perfect medieval town. Legend has it that Siena was founded by the son of Remus, one of Rome’s co-founders. This legend is reflected in the town’s crest, depicting the she-wolf who raised Romulus and Remus.

Siena spans three hills, and most tours of Tuscany will take you to the town’s central square, Il Campo. It is here that the renowned Palio is run, a treat for fans of equestrian sports. The Palio was featured in Quantum of Solace, the second James Bond film starring Daniel Craig. Other sights to see include the striking Palazzo Pubblico, overlooked by the Torre del Mangia. Both the Pubblico and Il Campo are among parts of the city built or rebuilt during the reign of the Council of Nine, between the years 1287 and 1355. Visitors can climb to the top of the Torre del Mangia, gaining unparalleled views of this postcard-worthy historical town.

San Gimignano

San Gimignano holds the accolade of having one of the most magnificent medieval skylines in the country. It’s this preponderance of dramatic medieval towers that has earned it the nickname of the Manhattan of Tuscany. Those of you planning on taking tours of Tuscany would be remiss not to make a stop at this beautiful, striking city.

San Gimignano is also easy to reach, being only around 30 or 40 miles south of Florence. Lying on the Via Francigena, San Gimignano’s location meant that pilgrims heading towards or leaving Rome would often stop there. The influx of wealth from these visitors elevated San Gimignano’s status and is the reason for the city’s wonderful skyline, initially built by the various merchants and nobles who lived in the then-prosperous town. While the town experienced a sharp downturn in its fortunes due to the plagues and famines of the fourteenth century, 14 of the original towers remain, along with a number of works of art produced by Italian masters.


History buffs planning on taking tours of Tuscany will find Monteriggioni a real treat. Its location, commanding a view of the Via Cassia, gave Monteriggioni heavy influence in the affairs of nearby Val d’Elsa and Staggia, as well as being strategically valuable to Siena as a lookout post.

Walking through Monteriggioni is a truly timeless experience, as the city has changed so little since it was built in the thirteenth century. Throughout its 800 year existence, Monteriggioni has only undergone three significant structural changes: in the sixteenth century the 14 towers were reduced in height and some earth was piled below the walls, and in the early twentieth century three of the aforementioned towers were brought level with the walls. Apart from that, the city’s structure remains completely original.

Fans of the Italian literary canon may recognise Monteriggioni from Dante’s The Divine Comedy, wherein the town’s turreted walls are used as a comparand to the giants surrounding the abyss.

These beautiful, historically valuable towns deserve to grace the itineraries of any historically-minded tours of Tuscany. With that said, there are plenty of other towns to explore in the regionScience Articles, not to mention the wild and stunning countryside.





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Rose Magers is an Australian-born Italophile and the founder of ArtViva. With an international reputation for excellence and creativity, ArtViva are at the forefront of escorted day tours in Italy. Rose has indulged her own passion for history and the arts by designing an innovative range of exceptional experiences and tours of Tuscany, from hiking and biking through the Tuscan countryside to unforgettable villa visits.


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