Engel & Völkers
  • 2 min read

5 most beautiful places to retire in Tuscany

Rolling green hills with scattered olive trees and distant mountains under a blue sky. Lush landscape with varying shades of green.

Tuscany is probably the most beautiful region in Italy that combines all the features of the Italian la dolce vita. There are beautiful landscapes, world-famous cuisine and charming medieval towns. Where could you find a better place to live? Here are the top 5 location in Tuscany.

Table of Content

  1. Siena

  2. Monteriggioni

  3. Montepulciano

  4. San Gimignano

  5. Chianti

Siena

Siena is a historic city in central Italy, located in the heart of Tuscany and it has been declared by UNESCO a World Heritage Site. The medieval city layout with its beautiful ancient buildings has survived and that makes Siena one of the most well-preserved medieval cities in Tuscany. Siena is a city with traditions; it is famous for its cuisine, art, museums, architecture and the celebrations. Every year at the beginning of July and in the middle of August Il Palio, a spectacular horse race around Piazza del Campo, is organized.

A scenic view of a hilltop town with historic buildings, lush greenery, and a bright blue sky with scattered clouds.

Properties in Siena and province

Engel & Völkers Siena

Monteriggioni

Monteriggioni is a small town, which is actually a medieval fortress located on one of the Tuscan hills, near Siena. It is one of the few such well-preserved medieval towns. From the 14th century, there were practically no changes in its architecture. Around the town, there are vineyards and olive groves typical of this area of Tuscany. The town appealed to producers of TV commercials. Native Fiat, as well as manufacturers from Western Europe, such as Citroen and Volvo, promoted their cars here.

Aerial view of a medieval walled village surrounded by lush fields and winding roads, set in a picturesque countryside landscape.

Montepulciano

Montepulciano is a medieval town of rare beauty highly recommended visiting in Tuscany. The city, full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners, boasts vast panoramas all over the wonderful Val d'Orcia and Val di Chiana valleys that surround it. Piazza Grande is the heart of Montepulciano and the setting for its main events, including the barrel-racing Bravio delle Botti contest held in August every year and much more.

A scenic view of a hilltop town surrounded by lush green fields and trees under a cloudy sky.

San Gimignano

San Gimignano is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy. Known as the Town of Fine Towers, the city is famous for its medieval architecture, unique in the preservation of about a dozen of its tower houses, which, with its hilltop setting and encircling walls, form an unforgettable skyline. San Gimignano is well known for its local products including saffron and white wine, the Vernaccia di San Gimignano.

Medieval townscape with stone buildings, tall towers, and lush greenery under a clear sky, capturing the historic charm.

Chianti

The Chianti area in Tuscany is one of the most beautiful in the whole region, as well as the most well-known and appreciated by visitors from across the world. Chianti offers a unique landscape, with green, gentle hills covered with wide fields of vineyards and olive groves, small stone villages, characteristic parishes and countryside homes in stone. Chianti also means wine. The label Chianti Classico is worldwide known and a producer association has been created to defend the quality and the uniqueness of the product.

Aerial view of a lush, green vineyard with rows of grapevines, surrounded by trees and rolling hills under a clear sky.

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