Popular Gaiole In Chianti Destinations

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Entire Villa6 Beds

Patio or balcony, Refrigerator

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Entire Villa7 Beds

Patio or balcony, Microwave Oven

About Gaiole In Chianti

Gaiole in Chianti is a comune or municipality in the Siena provice of Tuscany in Italy, located roughly 40 kilometers (or 25 miles) southeast of Florence. According to Forbes, its one of the best destinations on the list of "Europe's Most Idyllic Places To Live”. Surrounded by precipitous hills and narrow valleys, it is a charming expanse consisting of oak-filled forests, olive groves and vineyards. Gaiole has always played the role of a focal point for business and trade for the castles and towns nearby due to its strategic positioning at the foot of the valley. Since it was a marketing town, it never required defensive walls like those required by other areas in Chianti like Radda. However, constant clashes between Siena and Florence in the past probably accounts for why this center was damaged and reconstructed countless times; which in turn enlightens on the lack of intact historical buildings from the past. The influential presence of the Ricasoli family has been a controlling factor in the evolution and significance of the Chianti wine during the ages and even nowadays. They can track their ancestry back to the Firidolfi family. Their many castles now adorn the vast landscape, ideal for a day for villa and castle touring for history lovers. Find one that is to your liking with CuddlyNest and have a vacation of a lifetime!

Based to the east of Radda, Gaiole provides a taste of the battles for power over the centuries that shaped this land– amid Siena and Florence, and family struggles from the Medici family to the Ricasoli family and between the Guelfs to the Ghibellines. These clashes spurred on the fortification of the nearby towns and towering castles and many were marked by the continuous devastation, still seen today in the shape of so many destroyed towers and villas.

Getting there

From Panzano you can drive to Gaiole through 11 kilometer of a quiet rustic road, which will bring you a new appreciation for Chianti’s forests. If you come by bus you can take one from Siena to Radda, then to Gaiole. Once you arrive, it is easy to get around by foot and if you have a car, parking is available quite effortlessly, except for the more crowded touristic months.

What’s on the agenda?

In Gaiole, there’s much to get your heart racing – in a literal sense with L'Eroica, a yearly cycling event, and with lots of history and amazing food.


The exciting Castello (castle) di Brolio overlooks the southern Chianti Classico landscape for the past ten centuries. Positioned on top of a remote hill a few kilometers from Gaiole in Chianti, the castle’s origins are Lombardic and has belonged to the Ricasoli family since 1141. Although most of the castle is private for the present day Ricasoli baron family, the garden and the museum in Castello di Brolioare open for tours. The basic tour covers the gardens surrounding the castle and includes tasting wines at the wine shop. It is an hour long. The classic tour focuses on the winery and sampling wine, with an excursion of the cellars and vineyards of the estate.

Abbey of Coltibuono

Stop by the abbey, an ancient building. Surrounded by a wood filled with thick pines and evergreens, evidence has been found that supports the notion that that the building was given to Vallombrosan monks who transformed this little church into an abbey in the year 1037.

Known for their steadfast views against the widespread corruption in the clerical hierarchy of that time, the abbey flourished under their attention and with the help of donations. Until 1810 the circumstances at the abbey remained prosperous, when under Napoleonic rule the monks’ leaving was enforced. The abbey was then reclaimed and sold at an auction. Nowadays, the abbey houses a large farm and still is a striking and quite captivating building. Although not much of its original fortifications remain today, one of its highlights is an imposing bell tower.

Pieve di Spaltenna

It is a Roman style Pieve (rural church with a baptistery) of Santa Maria a Spaltenna, known to date back to 1030 based on a reference in documents found in the Badia a Coltibuono. It is a typical specimen of a Tuscan fortified settlement comprising of a monastery, a community church and a group of farms. The foundation is certainly much older and the bell tower is assumed to be from the year 1000. Earlier the monastery was a castle, which was gradually replaced by the monastic constructions that sprang up around the church. The whole compound became a benefice and was sought after by the richest families of the area. Eventually, the Ricasoli family became the owners of the Spaltenna and in 1708, it lost its standing as a parish church.

Castello di Tornano castle and vineyard

This ancient castle has witnessed 1000 years of conspiracies and battles. It is first mentioned in the year 790 during Charlemagne’s rule in Italy. During the two gory Aragonese attacks of 1453 and 1477 that led to the devastation of the main castles of the Chianti area, Tornano was able to endure due to its impregnability. It survived the impact well and was never occupied. Since the 1970s, Tornano Castle is owned and has been revamped by the Selvolini family of Florence to be the pride of Chianti. In present day, the castle is now available for vacations where you pretend you are to be the ruler of the castle in the Tuscan retreat of tranquility and sit down for a meal in their Ill Guarnellotto da Tornano restaurant.

Vacation Rentals at Mijas

To make your visit a comfortable one here, visit the CuddlyNest website for vacation rentals until you find the one that is suitable for you. It does not matter if you travel solo or with your family and friends – there is something for everyone! So for the best deals, book through Cuddlynest and enjoy your vacation time!

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