3+2 scenic Tuscany villages that will steal your heart forever

Tuscany is home to countless earthy heavens waiting to welcome you to idyllic landscapes and scenic scenery. Indeed, every corner has a different surprise, claiming a place in your heart. However, if you try to make a list of the must-see ones, then you get yourself into a huge challenge for sure. 

Although it’s impossible to suggest the top 10, for example, Tuscany charms to visit, we’ll make an effort to provide a first list of the 3 most fascinating and picturesque Tuscany medieval villages. If nothing else, they’ll pamper you with unparalleled beauty, spectacular vistas, charming buildings, and unforgettable experiences shared with your loved one(s). 

San Gimignano

San Gimignano

Tucked in the Siena province, this lovely Tuscan village enchants with its medieval appeal. Feel free to stroll through its cobbled streets and admire its 15 remaining imposing towers (used to be more than 70 of them in this region in the Middle Ages), ancient church with the gorgeous frescoes (known as Collegiata), and, of course, the heart-stopping views of the valley. Speaking of the surrounding landscape, an adorable hamlet with awe-inspiring medieval architecture called Certaldo in the Elsa valley (Florence province) will also give you incredible vistas of San Gimignano and its impressive towers!  

Photo by Matej Drha on Unsplash


The land in between Siena and Florence (aka Chianti area) is where you will find the dream-like Montefioralle village with the breathtaking panoramas and the remains of a still jaw-dropping castle enveloping stone houses with yellow walls. Olive groves, farms, vineyards, stretches of green pastures, and some of the best internationally-acclaimed local wines are things you can definitely expect from your visit here. And, if you happen to be around in March or May, don’t forget to join Festa di Frittelle (food event) and I vini del Castello (wine event) to skyrocket your Tuscany adventures.



Another absolutely adorable small village atop a hill near Siena that hypnotises with its fortified 13th-century citadel. One of the oldest and most representative of all Italian villages, its history dates back to the Middle Ages and has inspired Dante’s Inferno work. Besides the 14 towers and the perfectly preserved bastions and walls of its prominent castle, Monteriggioni magnetises with Santa Maria Assunta church – a keeper of the village’s medieval origins – and other historic chapels. 

As for local events worth your time and energy, do consider the medieval festival of Monteriggioni di torri si corona that attracts thousands of tourists every July. Also, the Slow Travel Festival that involves lots of entertainment, street performances, local dishes, music, and excursions and takes place in October, September, and June. 


Bonus option:

The hilltop village of Sorano is another superb addition to your itinerary that will caress your senses with tuff-rock-carved buildings, mind-blowing panoramas of river Lente, magnificent courtyards, maze-like alleys, dramatic arches, and a unique medieval allure swirling in the air. 


Tuscany is a balcony to sheer natural beauty and extraordinary endeavours that become the basis for unforgettable getaways. No matter what you expect to get from your visit here, chances are the final taste will hugely surpass everything you have envisioned! 

To perfect an already exciting Tuscany visit, you can choose one of the many uniquely elegant and stylish villas in the picture-perfect countryside, and get yourself VIP services and world-class experiences.



Featured Photo by Mattia Bericchia on Unsplash

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