A Road Trip through my Favourite Tuscan Villages

The landscapes of Tuscany might be familiar to many; however, it is only by roaming through the villages and walking on the seductive curves of the vineyard-covered hills that a visitor can grasp some of the serenity and healing calmness this region emanates. Life here is patient, mystic, and vivid, just like the wine that joyfully hums the years away in the silence of the barrels. The colours are succulent and tasteful, the open window shutters are an invitation to felicity, and attention to detail turns every moment into a unique experience.

Naturally, each village that dots the Tuscan map has a charm of its own. Choosing only a few seems unfair. Still, some left a stronger impact – an impression worth sharing – and below are details and photos to inspire any future visitor.

San Gimignano

With its 14 tall towers (meagre remains of the original 72 towers) that have turned this village into the iconic “Manhattan of Tuscany,” San Gimignano is undoubtedly a destination not to be missed. Like most villages in the region, it has been built on the top of a hill and the first signs of inhabitation date back to the Etruscan times. More solid constructions appeared during the Roman era in the 1st century BC, and, for several centuries afterwards, the village experienced a steady development, especially since it was conveniently located on one of the most important pilgrimage roads from Europe towards Rome. Its emblematic earmark – its towers – were erected during the 12th and 13th century, primarily as a sign of wealth and informal rivalry among the affluent families, each one competing on building the tallest construction as a proof of prosperity and power (some of the towers reached up to a height of 70m.) Finally, an order by the Council according to which no tower was allowed to be taller than the one adjacent to the Palazzo Communale put an end to this constructing frenzy.

The village was heavily weakened during the 1348 plague that decreased its initial population of 13,000 people by 70%. The decline continued until the 17th century, and San Gimignano reached an all-time low during the 1631 plague, with a reported population not amounting to more than 3,000 individuals. Growth came back from the 18th century onwards: many buildings were restored, and the village turned into a central touristic destination with increased agricultural production in the surrounding valleys.

Bigger and much busier than other Tuscan small towns, San Gimignano has kept its medieval ambience quite intact (mostly thanks to the slow economic development that lasted for almost four centuries). Admittedly, its alleys, full of delightful examples of Romanesque and Gothic architecture, are of breathtaking beauty.

Follow the signs towards punto panoramico and enjoy a dazzling view of the valley. Stay until the sun recedes behind the towers amply bestowing gold and lavender on walls and hills, and, if you are lucky, grab a table at the small café on that terrace to enjoy this nocturnal transformation over a glass of Vernaccia di San Gimignano (the famous local white wine produced by the ancient endemic variety of Vernaccia grapes). Do not omit the almost obligatory visit to Gelateria Dondoli, which proudly bears the title “The Best Ice Cream in the World” (a title that’s hard to support, despite the several awards, since ice cream in most gelaterias in Tuscany is simply divine). Pass by the artistic and historical museum SanGimignano 1300 where you can admire a stunning maquette of the village. And finally, be adventurous and don’t shy away from any passage, open door, art gallery, courtyard, or delicatessen in search of unmapped corners, the discovery of which will become a cherished memory, far beyond the typical to-do lists.

Montepulciano

Montepulciano, another gem on Tuscany’s treasure map, is renowned for its scenic roads, panoramic view of Val D’Orcia’s lavishly green slopes, and its delicacies: pork, cheese, and wine (Vino Nobile is considered among Italy’s best).

Despite the Etruscan settlements since the 3rd and 4rth c. BC and the subsequent Roman presence, the village – a loyal ally to Florence – enjoyed its golden period from 1390 till 1559, i.e., until Florence finally conquered its rival city, Siena. After that turning point in history, Montepulciano lost its strategic location advantage and gradually declined.

Visit the several small wineries that usually hide more secrets in the background than the mere bottles of wine displayed in the window. I was thrilled with Cantine Pulcino close to the village’s entrance, where wine and cheese ferment in an ancient Etruscan tomb, hidden in the shadowy cellar in the basement. Fall in love with the round pecorino heads ripening on wooden shelves, aromatized with red wine, spices, tomato, or even ashes. Indulge in wine tasting even as early as 10 am. Finally, enjoy the fulfilling bliss that simple, high-quality food brings to our lives.

Montalcino

Named after a variety of oak trees once covering the region, Montalcino is another typical medieval village offering stunning views of valleys dotted with olive groves, vineyards, and smaller settlements. Connected with Siena, it followed the latter’s history of wars and development and started deteriorating after it was conquered by Florence. Today, it is thriving mainly thanks to its distinguished Brunello di Montalcino, a wine produced entirely out of the Sangiovese Grosso grapes of the region and requires a long ageing process of 5 years. Despite being a very small town, it is divided – like most medieval Tuscan cities – into quarters, each one carrying its separate colours, songs, and drum beats. They all still meet twice per year in an archery contest where participants are dressed in medieval attire reproducing customs from bygone times.

If you reach the village at sunset, stand for a while at the small terrace close to the entrance and absorb the unfolding of the dusk’s veils over the ancient valley. It is guaranteed this will leave an indelible mark on your heart. 

Castellina di Chianti

Sometimes, a village is just cute and beautiful, and that’s enough. Such is the case with Castellina di Chianti, the entrance of which is decorated with the big black rooster standing on a red circle: the typical symbol of Chianti Classico found in all wine-producing villages of the Chianti region. The streets are few and colourful, wide open wooden shutters welcome the passersby into the mysterious cosiness of domestic life, flowers embellish every corner, and the shops offer typical Tuscan delights.

There hides a small local treasure: Gelateria in Paese, what the residents of Chianti consider to be one of the best gelaterias in the region – and, admittedly, it is! 

Monteriggioni

Even though this village is tiny – just a small community on the top of the hill, surrounded by ring-shaped walls of a total length of 570m – there is more to it than what initially meets the eye. This spot was of strategic importance during the Florence-Siena wars and, being closer to Siena, acted as a defensive fortification for the city. In 1554, control of the town’s garrison was handed over to Givannino Zeti who had been exiled from Florence and who, later within the year, reconciled with the Medici and offered the village’s keys to Florence – an act of absolute betrayal according to the locals.

The town is also mentioned in Dante’s Divine Comedy, its circular turrets used as a metaphor for the ring of giants encircling Hell.

Today, one can enjoy the medieval ambience evident in the typical stone buildings and the several armours decorating the entrances of shops or museums. Traverse the short road between the two main gates – Porta Fiorentina and Porta Romana, each facing towards the respective city; climb on the walls and walk along the circumference; and repose on the grass of a tiny park in the centre of the village, mingling freely with the few relaxing residents. 

San Donato In Poggio

This is another undisclosed little gem in the Chianti region. Despite its typical architectural style and lack of significant historical background, San Donato in Poggio is one of the most charming corners of Tuscany. There, we discovered – after local suggestion – the pizzeria Palazzo Pretorio where one can taste the best pizza in Chianti, a renowned baba dessert, and pannacotta with white chocolate and pistachios. We were also surprised by the town’s rather vibrant activity during the late evening hours. Even the biggest and most touristic villages seem to fall into sleep after 9 pm and dinner arrangements later than that time seem absurd and impossible. Still, in San Donato in Poggio, we had to wait till 10 pm to get a table, while the streets were dotted with a few coffee shops buzzing with locals enjoying the cool spring evening air. The reasons behind this increased nocturnal activity remain a mystery, yet the experience was very refreshing and joyful.

Radda

Was it the beautiful sunny day that made all flowers in Radda in Chianti shine even more brightly than normal? Or was it that, after a week in Tuscany, we had already learned to fall in love again and again with every picturesque corner? I cannot be sure. On the surface, Radda seems to be just another village in the region (even though one of the main wine-producing villages in Chianti); yet, there is something elusively special about it.

Sit in the main square, by the lion fountain, facing the decorated wall of Palazzo del Podesta and bask under the sun with a glass of wine. Explore the short subterranean medieval path dating – as per the sign – back to the 14th century, hiding a couple of very inviting cafes in its vaulted passageway. Check the shops that seem to offer a wider variety of merchandise compared to the standard tourist options, and, be ready to discover that, even though your stay was no longer than an hour or two, this was a village worth visiting.

Greve

With its triangular square and renovated medieval buildings in the old part of the town, Greve is scenic and quaint. Located in the heart of the enlarged Chianti region, it is famous for its wine and its olive oil (that is more delicate than the stronger ones from the south), its truffle hunting, and wild boars. The Cinta Senese boar is unique in the region and well-known for its high-quality meat. It should be noted that the town is home to Macellaria Falorni, one of the oldest and most renowned butcher shops in Italy. The wild pigs roam in the surrounding hills and forests, and we were told of several summer stories, when the heat pushes the animals into the green vineyards, or, sometimes, even into the pools.

Based on its agricultural production, its central location through an extensive road system, and the surrounding manufacturing facilities, Greve has developed today into the main market of the region. It remains comparatively vibrant even during the late evening hours and is a “must” destination for those interested in excellent Tuscan cuisine. Among the numerous options, make sure you visit La Castellana in the nearby Montefioralle (less than 1km away from Greve’s main square), where not only you will enjoy the exquisite food (try anything with truffles: it is simply superb!) but, above all, you will be treated as a guest in a Tuscan family home, feeling the essence of the famous local hospitality. Since the place is tiny, make sure you book well in advance.

Photo credits: © Konstantina Sakellariou