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Castelfranco di Sopra is one of Florence's fascinating "new lands," with its historic center still designed according to the typical medieval layout of orthogonal streets and a central square. From here, splendid views open up over the famous Balze del Valdarno, landscapes that even captivated Leonardo da Vinci. Walking through the village, you'll encounter unexpected treasures: the Palazzo Comunale with its 14th-century fresco of the Madonna del Latte, the Church of San Filippo Neri with works from the school of Andrea del Sarto, and, a little further on, the evocative Torre d'Arnolfo, a 14th-century medieval gate with the Florentine lily carved in stone. A village rich in history, art, and surprising views.

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One of the most interesting villages in the area actually hides a winery hidden within its walls.

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A romantic little town with lively bars. Located at the end of a dead-end street, it's beautifully quiet. Good hiking opportunities.

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Imagine finding yourself in the beating heart of the Chianti Classico, among the rolling hills of Siena. It is here that Volpaia began to take shape almost a thousand years ago, around the 12th century. Its strategic position, in an era of frequent territorial disputes, made it an ideal place to build a fortress. And it is precisely with this defensive spirit that the first residential nucleus was born, protected by solid walls that still define its perimeter today. During the Middle Ages, Volpaia was involved in the age-old rivalries between Siena and Florence, the two great powers that fought for dominion over Tuscany. Despite the tensions and changes of ownership, the village managed to maintain its identity and a certain autonomy. Its economy, since its origins, has been closely linked to the land and the production of wine and oil, a vocation that has been handed down to the present day. Over the centuries, Volpaia, while retaining its medieval structure, gradually transformed. The ancient fortified houses evolve into elegant residences, agricultural activities become specialized and the fame of Chianti wine begins to spread. The village, while remaining a small center, acquires a growing importance in the context of local wine production. Today, walking through the streets of Volpaia, you can still breathe that atmosphere of the past, but you can also perceive a vitality given by the presence of renowned wineries that have been able to enhance the historical and landscape heritage.

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Radda in Chianti is a spectacular medieval village enclosed by walls and located on the top of the hill that divides the Arbia and Pesa valleys. It has narrow streets and tower buildings typical of the period, together with the traditional Tuscan charm of local stone facades. In addition to the urban beauty, I can assure you that the view is also breathtaking: for this reason Radda in Chianti is undoubtedly worth a stop!

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Brolio Castle, located in Gaiole in Chianti, bears the signs of the most diverse eras of which it is a witness: from the medieval bastions, to the Romanesque, neo-Gothic theme, up to the Tuscan nineteenth century. It is currently managed by the Ricasoli farm, which thanks to the surrounding land, has masterfully produced wine and oil for hundreds of years. The building can be visited and, by consulting the website, it is possible to find different types of tours and tastings.

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Radda in Chianti is a typical Chianti village surrounded by vineyards, where the permanent route of L'Eroica passes. In addition to a walk through the streets of the center, a tasting of excellent Chianti Classico, take a photo of the heart of the village, Piazza Ferrucci, dominated by what remains of the original castle, overlooked by the Palazzo del Podestà.

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You meet this castle at the end of the first ascent of the Eroica, coming from Gaiole in Chianti. The castle deserves a refreshment/water break after the climb, to then set off again on the white brackets towards the rest of the first heroic stage.

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