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Gaiole in Chianti: what to see, where to eat and sleep in the most enchanting part of Chianti

Between millenary castles and a nature that is pure wonder, our tour continues among the pearls of Chianti

Its origins date back to the Middle Ages, in its square you can see the state of a black rooster, symbol of Chianti. We are in Gaiole in Chianti, halfway between Chianti and Valdarno, inhabited by about 2,300 inhabitants, situated along the course of the Massellone stream, the village developed from the 13th century as a market place, becoming one of the chief towns of the tertiary division of the Lega del Chianti, together with Radda in Chianti and Castellina in Chianti.

It is in Gaiole that the Strada dei Castelli (Castle Route) originated: among the most beautiful are the Castle of Cacchiano, the Castle of Brolio, Meleto, Vertine, San Polo in Rosso and the Castle of Ama, the latter famous - as well as for its wine production - for the numerous works of contemporary art housed inside. Back in the village, stop for a glass of wine in the main square.

Gaiole is inextricably linked to L'Eroica, an event evocative of cycling in times gone by that has captured the attention of many enthusiasts around the world. It takes place every year at the beginning of October, mostly on unpaved roads in the Chianti Senese area, and the rules state that you must take part on a vintage bike.  There are two routes available: the long one of 205 kilometres and the medium one of 135. Start and finish right here, in Gaiole in Chianti.

The art collection of the Castello di Ama, where Grandi Vini di Terroir are produced, is set in a landscape of extraordinary beauty and focused on two fundamental notions: the in situ installation and the relationship with the genius loci. Works by Michelangelo Pistoletto, Daniel Buren, Giulio Paolini, Kendell Geers, Anish Kapoor, Chen Zhen, Carlos Garaicoa, Nedko Solakov, Cristina Iglesias, Louise Bourgeois, Ilya and Emilia Kabakov, Pascal Marthine Tayou, Hiroshi Sugimoto, Lee Ufan, Roni Horn, Miroslaw Balka, are located between the modern winery and the complex made up of the old cellars, the 18th-century villas with their chapels, the gardens and the vineyards that surround the village (www. 

The medieval heart of Gaiole and the whole of Chianti is the Castello di Brolio, still a symbol of the tradition and great winemaking history of Baron Ricasoli. The castle came into the possession of the Ricasoli family in 1141. Generations have traced its history: from the eternal battles with Siena to the unification of Italy. Bettino Ricasoli, the 'Iron Baron', was to be Prime Minister in post-Cavour Italy, but also the inventor of Chianti wine. Today, the family still heads Italy's oldest winery.

The medieval village of Vertine is situated on a hill 357 metres above Gaiole in Chianti.
he castle, or rather the 'walled village', of Vertine stands on the extreme north-eastern edge of Chianti, close to a series of hills, known as the Monti del Chianti, which form the watershed with the Upper Valdarno. This area is particularly rich in castles as it corresponds to the territory of the medieval Lega del Chianti, a Florentine bulwark on the border with the territory of Siena.  The splendid worked stones used for the construction of the walls and the keep can also be found in the buildings inside. The whole gives Vertine a typically medieval image and brings the visitor walking along its narrow streets back into contact with the reality of the past.

Castello di Meleto stands majestically in the enchanting landscape of Gaiole in Chianti, at the end of a pleasant avenue lined with cypresses and junipers. For over a thousand years, Castello di Meleto has dominated its lands and vineyards. Today, as in the past, Castello di Meleto is an unspoilt oasis where visitors can spend unforgettable moments surrounded by the Tuscan hills. A visit to the castle halls and the historic wine cellar is a must.

Spaltenna - a locality near Gaiole in Chianti - is mentioned as early as the beginning of the 11th century in some parchments of the abbey of Coltibuono. The parish church of San Pietro in Avenano was transferred to Spaltenna between 1102 and 1110), which took the name of Santa Maria a Spaltenna and was transformed into a 'munita' parish church.  The name of San Pietro in Avenano was retained until 1153 when, in the bull issued by Anastasius IV to the bishop of Fiesole, the church was cited by the pope as the pieve of Santa Maria a Spaltenna. Next to the parish church is its restored farm. The farm with the monastic premises, which was owned by many churches, was a benefit coveted by the wealthiest families of the time, who sought to possess it: Santa Maria a Spaltenna became the property of the Ricasoli family, who also owned the land and farm of the pieve of San Polo in Rosso. The interior is a Romanesque church with three naves and an apse. The walls and the bell tower are made of ash-coloured alberese stone. The façade has a rectangular opening.

The Badia a Coltibuono winery is an undisputed point of reference for the quality and longevity of its wines, as well as its respect for the land, attention to sustainability and artisanal production methods in both the vineyard and the cellar, despite the not insignificant number of hectares and bottles. Badia, as its name suggests, is an ancient medieval abbey, San Lorenzo, dating back to 1051 and home to an order of Benedictine Vallombrosian monks, the "revolutionaries" of medieval agriculture. Coltibuono also refers to agricultural activity, from the Latin cultus boni, and the agricultural symbol in the monastic order's coat of arms, now the winery's logo, is emblematic. 
After Napoleon's privatisation of the abbey and the succession of owners, Badia a Coltibuono has been in the hands of the Giuntini/Stucchi Prinetti family since 1846.

The village of Castagnoli rises up from the heart of the Chianti Classico region, on a hill that the Etruscans already knew very well. From there it dominates the surrounding valley from the top of a hillock that brings to mind remote times, surrounded by woods, vineyards and olive trees.

The Rocca that bears its name covers about 850 hectares of property with elevation profiles ranging from 860 metres (Monte Luco hill) to 380 metres. There are 92 hectares of vines, mainly Sangiovese, the base grape for the highly prized Tuscan wines produced.

Osteria di Brolio. Wrapped in the embrace of Chianti, the Osteria di Brolio is the place where the flavours, scents and landscapes of Tuscany come together. A pleasant terrace is ready to welcome guests in the green, under the walls of the Ricasoli family's castle of the same name. Thanks to its desire to respect tradition and use quality raw materials, this restaurant is certainly a certainty for all those seeking genuine flavours. In addition, a great novelty accompanies the reopening of the Osteria: the return of Franco Sangiacomo, a well-known hospitality professional. The restaurant service is open every day (except Thursdays) for lunch and dinner.

Il Pievano, Castello di Spaltenna - One Michelin star. In the charming, romantic atmosphere of a thousand-year-old convent, whether you dine inside in the hall of the popes or at the tables set up in the suggestive internal courtyard you will - in any case - be in the reassuring hands of a young chef of Greek origin. Long in love with Tuscan cuisine, Chef Stelios Sakalis will offer you a brilliant essay, between refined presentation, a remarkable research of products (especially among the local breeders) and the ability to "translate" everything in a delicate and balanced way.

Osteria il Papavero. To get to Barbischio, a very old medieval castrum, you have to go up to the "upper floor" of Gaiole. In other words, you have to land high up in the hills. And by the way, you must stop at the Osteria Il Papavero, an ancient village shop converted into a restaurant. Because a few words are enough to describe an enchantment. The old floor of the small and unique dining room alone is worth the trip. The kitchen responds in kind with a series of carefully prepared dishes that are never predictable, where the sensitivity of the chef-patron, a "migrant" from the Maremma, is revealed through his thoughtful reinterpretation of traditional dishes, sometimes playing "by subtraction", and repeatedly demonstrating a sure hand in the cooking, balancing and layout. And if the wine list is a bit limited, you will still manage to drink well, especially if you rely on certain Chianti Classico wines from the Gaiolo area.

The Ristoro di Ama, on the farm of the same name in Gaiole in Chianti, has a traditional menu that includes panzanella, pappa al pomodoro, potato ravioli with white meat sauce and Chianina beef tagliata. The wine labels are all home-grown.
Badia a Coltibuono. One of the cult places for food and beauty in Chianti. Adjacent to a cosy agriturismo on the same property, with a large panoramic garden for the summer, it offers revisited Tuscan recipes. Of particular note: cod escalope confit with Taggiasche olive pesto and citron and fennel salad; spelt flour pappardelle with stewed wild boar with juniper; roast leg of lamb with liquorice sauce and artichokes al dente; braised veal cheek with sweet and sour shallots; pistachio sbriciolona and Vin Santo di Badia a Coltibuono.


And finally, for a regenerating weekend in the most extraordinary Chianti, here are the structures that could be right for you: Villa Ricucci with its five suites overlooking one of the most evocative landscapes of Chianti and the vineyards of Ama, from which they take their name. Castello di Spaltenna Exclusive Resort & Spa: refined and welcoming charming relais with Spa and swimming pools, Rocca Di Castagnoli with a magnificent outdoor swimming pool surrounded by its own vineyards, rooms and suites. Badia a Coltibuono charming agritourism in the Chianti Mountains: the road to get there is a thrill in itself, Badia a Coltibuono is the first wine resort in Chianti and offers a truly unique experience in the historic setting of a 1000-year-old abbey and farm and finally Castello di Meleto: 19 rooms set in the unique context of a medieval castle and outdoor pool.


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