Castellina in Chianti Castellina in Chianti is a city located on top of a beautiful green hill, seperating the Pesa and Staggia river. This small town is situated at the road that connects Florence to Siena, called the Via Chiantigiana. Castellina in Chianti is a historic town, with origins going back to Etruscan times. It was an important outpost because of its position between Florence and Siena. During times of battles, the city was destroyed and rebuilt many times, increasing the defensive walls every time the town was reconstructed. The Via della Volte is a covered street or tunnel, situated along the ancient walls, once used by guards, now used for shops and restaurants. You’ll be able to find more shops at the main street of Castellina in Chianti, called the Via Ferruccio, but also beautiful places such as Palazzo Banciardi and Palazzo Squarcialupi. These palaces both belong to local important families and the Palazzo Squarcialupi already serves as a wine shop for over 100 years, where you of course will find the delicious Chianti Classico wine. Just outside the city centre, the Fortress with its tall tower can be found, which offers a great view over the town and countryside. Another place that must be visited as well is the Church of San Salvatore, dating back to the 16th century, built in neo-Romanesque style. It contains important frescos, statues and a crucifix. If you like archaeology, the Archaeological Museum of Chianti is definitely something for you, where an Etruscan tomb buried under a tumulus on Monte Calvario and Etruscan necropolis of Poggino can be found. Castellina in Chianti is located at approximately 55 km from Florence, so the easiest option is to fly to Florence and take the car from there. Another option is to fly to Pisa, which is around 100 km from Castellina in Chianti and take the car from there as well.

The most known and visited area of Tuscany is the Chianti area, comprising around eight Chianti towns. The borders of this area aren’t very clear, but it can be said that in general it extends over the provinces of Florence and Siena, covering all of the area between the two cities and extending to the east toward the Valdarno and to the west to the Val d'Elsa. The Chianti landscape is unique and very beautiful, including picturesque little village, forests and hills covered with vineyards and olive trees. This region is of course also famous for its outstanding red wines, presented in bottles in woven baskets. The Chianti wines are characterized by intense aromas of fruit and flowers, easily drinkable with a smooth aftertaste. Traditional farming is still an everyday part of life in this region, including as afore mentioned wine making, but also olive oil production is very important here, making this region so attractive to tourists. 

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Emiliano (8 persons) - Italy, Tuscany, Montaione

Villa popularity 2024: 74% booked

Montaione, a cozy, small hamlet in Tuscany near Florence, hailing from the earliest settlements during the Etruscan and Roman age, is also famous because of its location a few kilometers only from the Sacro Monte di San Vivaldo, that is an exact rep... read more »

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8
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€ 4.802,-

Norah (8 persons) - Italy, Tuscany, Gaiole in Chianti

Villa popularity 2024: 98% booked

This splendid property is located in one of the most beautiful parts of the Chianti Classico area. The complex has recently been very carefully and tastefully renovated, and is perfectly furnished with traditional Tuscan pieces and fitted with all m... read more »

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Paola (10 persons) - Italy, Tuscany, Siena

Villa popularity 2024: 100% booked

An old farmhouse, 4 Km from the center of Siena, situated on the top of a hill from which it is possible to admire the Chianti hills on one side and the Val d'Orcia on the other.  The stone building is surrounded by a beautiful, completely fenc... read more »

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Citycenter
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10
private pool
4 km
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Ludovica (8 persons) - Italy, Tuscany, Porto Ercole

Villa popularity 2024: 71% booked

Porto Ercole is a delightful seaside resort located on the promontory of Argentario.  It is an ancient fishing village which lies at the foot of a 16th century Spanish Fortress. Visitors can enjoy pleasant walks around the town’s alleyway... read more »

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Beach
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8
private pool
1 km
€ 8.673,-

Sienna (6 persons) - Italy, Tuscany, Buonconvento

Villa popularity 2024: 100% booked

This characteristic detached house is located amidst the Crete Senesi, 6 Km from Buonconvento and 13 Km from Montalcino, on top of one of the area’s typical gentle hills that offer stunning panoramic views of the valleys that change color acco... read more »

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6
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Martina 22 (16 persons) - Italy, Tuscany, Buonconvento

Villa popularity 2024: 78% booked

The prestigious Martina 22 is located within a 600 hectare estate on the hills of the Val d'Orcia, between Siena and Montalcino.   This historic place has been recognized by UNESCO as a key reference point for the area. The Castello... read more »

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16
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€ 35.973,-

Martina 16 (16 persons) - Italy, Tuscany, Buonconvento

Villa popularity 2024: 98% booked

The prestigious Martina 16 is located within a 600 hectare estate on the hills of the Val d'Orcia, between Siena and Montalcino.   This historic place has been recognized by UNESCO as a key reference point for the area. The Castello... read more »

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Beatrice (13 persons) - Italy, Tuscany, Monteroni d'Arbia

Villa popularity 2024: 99% booked

Beatrice is located in the middle of a 400 hectare organic farm, delimited by a small, very ancient village. It is situated within the Crete Senesi, a very atmospheric landscape dominated by harsh, bare hills worn away over the centuries but wh... read more »

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13
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Elisabetta (8 persons) - Italy, Tuscany, Vertine

Villa popularity 2024: 64% booked

Elisabetta is situated in a little village that dates back to the Middle Ages, 40 Km from Siena and 3 Km from Gaiole in Chianti, in an area filled with castles and magnificent vineyards: the birthplace of Chianti Classico wine. The village of Vertine ... read more »

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8
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€ 3.150,-

Xavier 12 (12 persons) - Italy, Tuscany, Gaiole in Chianti

Villa popularity 2024: 98% booked

The Chianti region is not large but it is very rich from a naturalistic viewpoint, with a valuable historic and artistic profile and a generous offering of food and wine. The Chiantigiana, one of the most beautiful roads in Italy, crosses the whole ... read more »

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12
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Xavier 8 (8 persons) - Italy, Tuscany, Gaiole in Chianti

Villa popularity 2024: 98% booked

The Chianti region is not large but it is very rich from a naturalistic viewpoint, with a valuable historic and artistic profile and a generous offering of food and wine. The Chiantigiana, one of the most beautiful roads in Italy, crosses the whole ... read more »

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8
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Margo (8 persons) - Italy, Tuscany, Peccioli

Villa popularity 2024: 98% booked

Margo is 8 Km away from Peccioli, a charming medieval village perched on a hill with a wonderful view of the Tuscan countryside. In the village guests will find a selection of restaurants, bars, a historic cake shop and stores for everyday ... read more »

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8
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Sophia (10 persons) - Italy, Tuscany, Peccioli

Villa popularity 2024: 98% booked

This elegant liberty style villa dating back to the mid 1900s has been renovated without altering its architectural features.  Furnished extremely tastefully in every detail, the original 19th century pieces and ornaments give the villa a parti... read more »

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10
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Diego (12 persons) - Italy, Tuscany, San Donato in Poggio

Villa popularity 2024: 98% booked

The Chianti region is made up of gentle valleys and picturesque villages that will capture your imagination, offering breathtaking natural and architectural landscapes and giving you a taste of the warm Tuscan welcome for which this area is so famou... read more »

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12
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Irene (14 persons) - Italy, Tuscany, Montenero

Villa popularity 2024: 90% booked

Old detached farmhouse dating back to 1800 situated in the green Tuscan countryside along the coast of Livorno just 4.5 km from the area’s small beaches and 8 km from the center of Livorno. The farmhouse has been renovated without altering the... read more »

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14
private pool
4 km
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