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Village Hopping in Tuscany

 “[..] in seemingly small places there is such depth beyond the surface in which to indulge.”

Letting go of the summertime in Italy is never easy, particularly from the central to the southern regions. By mid-October, even the warmest parts of the country must fold up their lettini until the succeeding summer season. The days grow cloudier, cold breezes stem from the sea and roll over into the hills, making for chillier days and nights and winter attire emerges from whatever dark shelf they were residing on before. 

Lucky for Tuscany, changes in climate take nothing away from the attraction and leisure that the region has to offer. Once the temptation to spend endless days by the seaside has been eliminated, it opens the door to a particularly entertaining activity; village hopping. Village hopping is arguably the best way to discover Tuscany, a place sprinkled with an abundance of charisma and authenticity, begging to be explored. In my experience, the activity has entailed day trips or evening strolls around new locations over a series of weekends, spending just the right amount of time having a meal, interacting with locals, and absorbing the atmosphere over the course of a few hours. The enriching quality of village hopping in Tuscany, particularly around Maremma, is how in seemingly small places, there is such depth beyond the surface in which to indulge. Two particularly special places, Magliano in Toscana and Pitigliano, carry very niche experiences despite being just an hour apart.


Magliano in Toscana

Surrounded by one of the oldest and most intact fortifications in the region lies the centro storico of Magliano in Toscana. The walkways upon the walls built around the town, constructed between the Medieval 13th century and the 15th century Renaissance period, provide charming views which stretch over rolling hills and onto the distant seaside. Mysterious and eerie tales are to be discovered in Magliano, such as l’olivo della strega, which is one of the oldest trees in Italy, or the Abbazia di San Bruzio, a 12th century monastery with elegant Romantic architectural features (such as gothic-style ornamental carvings and arches), each adding a layer of character, history, and legend to the subtle village hidden within the inlands of the Maremma. L’olivo della strega, for example, earns its name from the legend that it was a gathering place for witches— one witch in particular, during her ritualistic dances, tugged and manipulated the branches of the tree until it contorted into its present form. She then transformed into a cat so that she could watch over the tree, ceasing to return for several centuries. On the other hand, the Abbazia di San Bruzio holds more hair-raising tales, ranging from the legend of Destiny, about a girl who suffers an unfortunate end due to her gamble with love and destiny, to rumours of the secret activities of nuns who sought to flee the outside world. These stories bring life to the various landmarks scattered around the village, making for a more immersive visit.

In the colder months, Magliano in Toscana grows into a quieter place. Upon my first encounter, wandering in through the Porta Nuova on the western side of the town, the uniform stone facades and well-kept streets were immediately inviting. The complex history of the village is apparent from its aesthetic, particularly seen in the Palazzo di Checco il Bello, or the Chiesa di San Giovanni Battista. These are both structures which emanate traces of gothic and Romanesque architecture that were typical of the periods in which they were built; simple with regard to the palazzi and chiese in larger Tuscan cities, such as the Duomo di Siena with its intricate marble facade or the grandeur of the Palazzo Vecchio in Florence, yet alluring in a modest way. 

A notable fact about Magliano in Toscana is the impeccable quality of dining. A number of the best restaurants in the region reside in the cavities of these quaint streets, Da Guido is a personal favourite. Dining there is an experience, with fantastic local wine to accompany the warm and heavier dishes which we all crave once autumn commences. A meal at Da Guido immediately launches with an array of various antipasti that seem to never-endingly emerge from behind the kitchen doors, a mixture of cheeses, meats, and vegetables— and that’s only the beginning. The clientele of the restaurant is an ode to the quality of the meal, attracting both locals and an array of international diners. During my last visit, for example, on a seemingly “quiet” Sunday evening in the village, Da Guido was bustling with people from all over: a university age couple in a heated debate, a large older group of friends indulging in their slow catch-up, a family trying to keep their toddlers seated at the table, and an English speaking couple unsure of when to stop eating, among others. If you even try to refuse one of the included antipasti that continue to squeeze their way onto the table, the waiter will claim, in an insistent tone, that Guido himself would like you to try the dish— even just one bite. When we asked to try just one of the gnudi al tartufo, the waiter came out with three for each of us. There is no diet to be maintained within the walls of Da Guido, the only tip that can be provided is to ensure you arrive hungry. A plate of tagliolini al tartufo and a glass of red wine on a chilly night in Magliano is what I envision as the ideal weekend night away from the city. 

After a few visits, the village grew to be more homely, as I started noticing the same white Persian cat wandering around the same street corner as the year before. The man in Bar Camelot began to recognise us, always preparing the most impressive aperitivi, boards filled with the region’s best cheeses, despite giving the impression of a simple bar. The lights illuminating the walls surrounding the town emphasised the looming presence of this secret in the Maremma countryside, imposing itself as a recurring location in my rounds of the region.


For a more dynamic experience, Pitigliano is my recommended place to occupy one of those sunny autumn or winter days. With a history stemming from Estruscan roots and inhabited as early as the Neolithic Age, the centro storico of Pitigliano is a privilege to explore. After driving through some winding woodland roads, the most impressionable view struck me in a way not many places do. Pitigliano is suspended precariously on a cliffside, towering over the lush greenery below and regally overlooking a small valley. It was not long before I discovered the vast breadth of history sheltered behind the building fronts, the outward enchantment of the town also extending inwards (and beneath the ground). 

As if the village itself is not engrossing enough, every step revealed a new element of curiosity and discovery. Built by a prominent Jewish community in the latter portion of the 16th century, an underground city resides just beneath the Jewish Ghetto, among the other structures of the town with immense historical significance. The “underground city” is an extension of the Jewish quarter of the town, with various rooms and spaces excavated by both the prominent Jewish community and the Estrucans. Beneath the surface one can encounter tombs, chapels, stables, and maze-like tunnels intricately woven into volcanic tufa rock on which the village is built upon. Notably, alongside other underground amenities, the Etruscans also uniquely carved a deep ravine by the name of Via Piave which surrounds Pitigliano on all sides. I spent an afternoon wandering this portion of the town, never quite registering the incredible preservation of the past in this place off the beaten path. The Medici Aqueduct, Palazzo Orsini, and further extensions of ancient architecture also continue to provide depth to this cliffside village.

Beyond the town, though, is one of my favourite and ideal ways to absorb the Maremma area; by horseback. Not far from Pitigliano, Maneggio Belvedere describes themselves as a place “situated in a particular area, where for years, forgotten by means of mass media and far from main Italian roads.” They aim to bring attention to the surrounding uncontaminated nature, their seasonal production of wine, oil, beans, cheeses, and more delicacies, and the hospitality of the people of this region, wherein “se trovate una cantina aperta, quasi sicuramente vi offriranno un bicchiere del loro vino”. The long gravel road leading up to the horse stable and equestrian centre is flanked on one side by fields owned by local farmers, and on the other, horses grazing. 

Maneggio Belvedere has been one of the best ways I’ve connected with the region, not only through the activity itself, or the sights I’ve seen, but also the flow of anecdotal entertainment from Andrea, the owner of the stable (alongside his wife Brigitte) who guides each ride. As we wander through thick brushes of forest or through open fields, Andrea always has a comedic tale reminiscing his youth. The various altercations and encounters of his boyish past bring life to the quietude of the surrounding fields and forests we overlook during the two hour ride. There is arguably no other way to reap the natural beauty than from horseback, illustrating views from above through the Tuscan hills as well as through the streams below: a dreamlike scene inaccessible with any vehicle and too ambitious to reach by foot. 

From quaint Medieval towns, to cliffside Roman aqueducts, from tartufo tagliolini to breathtaking views from horseback on the tops of lush hills, I’ve never found a dull moment during these Tuscan rendezvous. The list of places to stumble upon in a region so rich with culture, history, and elegance is inexhaustible, and conveniently, it keeps me content, full, and captivated at the turn of every season.

Abbazia di San Bruzio

Palazzo di Checco il Bello

Chiesa di San Giovanni Battista

Ristorante da Guido

Medici Aqueduct

Maneggio Belvedere

Palazzo Orsini

Olivo della Strega

Porta Nuova