Agriturismo Villa Palagetto San Gimignano - Siena La Lastra Siena Visit of vineyards
and cellar with wine tasting and light-lunch Farmhouse La Lucciolaia San Gimignano - Siena Agriturismo Cesani San Gimignano - Siena Luxury villas for rent in Tuscany


Montespertoli in ancient times, the Etruscans inhabited these lands, but Latin place names are mostly reminiscent of the numerous Roman settlements that flourished here.

History of Montespertoli
MontespertoliIn ancient times, the Etruscans inhabited these lands, but Latin place names  are mostly reminiscent of the numerous Roman settlements that flourished here.
The presence of the Romans is confirmed by the abundance of archaeological findings, among which memorial stones in Santa Maria a Torre, in Ortimino, and in San Piero in Mercato.
The Lombard invasions were the first step towards the creation of present-day Tuscany, the 'Tuscia Longobardorum' opposed to the 'Tuscia Romanorum'.
During this period, in fact, local populations developed a road system that suited the features of the local lands, which have a geographical conformation that includes valleys interconnected by means of important roads.
The scarcity of medieval archaeological relics does not provide specific references for all the villages, but at that time Lucardo must certainly have been one of the main settlements in the area, as well as the most significant village around Montespertoli owned by the Nonantola abbey.
The Franks were replaced by the Lombards and a slow but ongoing process led to the creation of the characteristic political setup of the feudal period. Tuscany became one of the first marquisates in Italy, reaching the peak of its power before the year 1000 thanks to the Marquis Hugh of Tuscany (888 - 962), but already in the second half of the 11th century local towns started to strive for independence.
This was due to the development of new social classes such as the bourgeoisie, which would later lead to the birth of the form of local administration known as Commune or City State.
The Papacy and the Empire were the most influential political forces in the Middle Ages and all the big feoffees bore allegiance to either of the two. Meanwhile, the towns' autonomist tendencies became stronger and stronger and their power extended to the surrounding countryside, at the expense of the feoffees.
The 12th century was dominated by the struggle between feudalism and the bourgeoisie of the city states, which was the starting point for the creation of new rural communities, eager to redefine the relationships with landowners in order to be granted the participation in the government of their own communities and less unfavourable terms to regulate their farming activities.
MontespertoliThe birth of the Municipality of Montespertoli occurred within the framework of the struggle between the feudal lords and the Florentine republic, which since the beginning of the 12th century had fought for its independence, liberating itself from the imperial influence represented by the marquises of Tuscany.
Some of the feudal lords decided to move into the towns, accepting the new course of history and taking on public duties in the Republic, but others kept fighting until the final defeat inflicted upon them by the Florentine army.
The fall of the Alberti Counts and the handing over of the Pogni and Semifonte castles marked the start of a different evolution.
As soon as villages freed themselves from feudal lordship, they united in small autonomous federations, called "populi", which were under the civil jurisdiction of Florence but were so proud of their independence and of their ancient origins that, instead of referring to the city's authorities, they exclusively referred to the local parish church and its parish priest, sometimes replaced by magistrates called "rectors", elected by the citizens of each single community.
Churches were the centers of religious life, but they were also used for public assemblies, thus taking on the true role of 'Pieve' (parish church), a word which derives from the term plebs, the people's church.
The 'Piviere' was therefore the original and first form of rural municipality in the Florentine countryside around the 13th century. Later, some 'pivieri' joined together and formed the so-called "leghe di popolo" or "leghe comunali" (people's leagues or city state leagues).
The first league in the Montespertoli area derived from the union of the 'pivieri' San Piero in Mercato, San Pancrazio, and Coeli Aula, and took on the name of the first Church that was the Podestà's residence. The league had as its coat-of-arms the keys of the parish church of 'San Piero', together with the lily symbolizing the allegiance to the Lega da Firenze (League of Florence) and the star, indicating the long-established authority of the Alberti Counts in the area.
Montespertoli CastleMontespertoli Castle
The castle stands beside the village of Montespertoli and is owned by the Sonnino family, but it once belong to the Lords of Montespertoli, a branch of the Counts Alberti da Mangona; in 1393, the family became extinct and the possessions of the Lords of Montespertoli passed to the Machiavelli family. The properties of the Macchiavellis stretched over almost two thirds of what is today the Borough of Montespertoli and the family donated several works of art to local churches, enriching them with remarkable masterpieces.

Montegufoni Castle
It was owned since 1160 by the powerful Acciaioli family, whose most famous member was Niccolò Acciaioli. At that time, the castle was a castrum made up of seven buildings, each separated from the other and used to house craftsmen and farmers, who worked for the castle's owners, and encircled by the walls surrounding the entire complex. Later this set of buildings became the castle, as we know it today, and it was further renovated in the 17th century. The first intervention by Ottaviano Acciaioli, who added forty rooms to the building in 1632, was followed by the most noticeable renovation, which would bring about the biggest changes to the castle's structure.
Montegufoni CastleA wonderful garden was added to the villa, thus complementing its striking architecture and creating endless connections between open and closed spaces. Water games, caves encrusted with stalactites, luscious plants of different species turned the garden into a place of delight, sought after by noble families that loved to spend their time there, including the Medici family. The presence of artists, poets, and comedians, welcomed by the liberal and renowned owners of the castle, contributed to turn Montegufoni into a place of culture and refinement.
In more recent times, when the Acciaiolis no longer owned it, the castle had a different history. It was purchased by Sir George Sitwell, an extravagant member of the English aristocracy, which gave new impulse to the castle's life. Before moving in permanently, he restored the property without accepting other people's advice on how to carry out the renovation and asked Gino Severini to decorate it. The artist painted his Arlequins in the Acciaioli halls and the proposal by Sitwell's sons to let the young painter Pablo Picasso decorate the walls was turned down by the father. During the First World War, the famous "Primavera" (Allegory of Spring) by Botticelli and other masterpieces of the Uffizi museum were hidden here. Its wonderful tower was built drawing on the architectural model of the Tower of Palazzo Vecchio in Florence.

Poppiano CastlePoppiano Castle
The Poppiano Castle was an imposing medieval building with three rings of walls, built around the year 1000. It was used as a fortress for the external defense of Florence and, as testified by an inheritance document of 1199, it has belonged to the Guicciardini family for at least nine centuries. During this long period, it has been the center of many episodes linked to the history of Florence. Among the most remarkable events, in 1369 John Hawkwood, the famous English Soldier of Fortune, who had just fought the battle of Fosso Armonico, near Cascina, set up his camp in the Poppiano Castle. The Castle was partially destroyed in 1529 during the siege of Florence, as mentioned by Francesco Guicciardini in his 'Memorie'. Despite still showing its ancient magnificence, the structure of the castle, as we see it today, bears evident signs of the renovation that followed the destruction caused by an earthquake in 1812 and that was carried out on the basis of frescoes from other Guicciardini villas in Val di Pesa and Val d'Elsa, which depicted the original structure of the castle. Since the 1200s, the Guicciardinis held a key position in the political, social, and economic life of Florence and in 1416 Piero Guicciardini was nominated "Count Palatine" by Emperor Sigismund of Luxemburg. The family actively participated in Florence's public life and gave the city 44 "priors", 16 "gonfaloniers of justice" and 12 senators. The most important personality of the family was Francesco, called the Historian (1483-1540). After having held relevant posts for the Medici family - ambassador in Spain, Governor of Modena and Reggio, Leader of the League of Cognac - he moved to Florence and Poppiano, where he wrote a part of his most famous book, "Historia d'Italia".

Montespertoli: discover the surroundings

Accommodations in the area

    • Firenze (Florence)
    • 16 km from Montespertoli

    Marignolle relais & charme

    The charming Marignolle Relais & Charme, nestled the hills of Florence, is the ideal solution for those who want a place of excellence and relaxation and love peace and privacy without the amenities of a luxury hotel.
    Marignolle Relais & Charme is especially appreciated by travelers looking for style and tradition by offering deluxe rooms or junior suites in a refined, with superior comforts and impeccable services that make this relais an excellence of Florence.

    Booking ONLINE

    • San Gimignano (Siena)
    • 17 km from Montespertoli

    Agriturismo Cesani

    Azienda Agricola Biologica Cesani is an organic farm nestled in the rolling hills of the Tuscan countryside, in the tiny country hamlet of Pancole, 6 km to the medieval town of San Gimignano.
    Azienda Agricola Biologica Cesani is an organic farm nestled in the rolling hills of the Tuscan countryside, in the tiny country hamlet of Pancole, 6 km to the medieval town of San Gimignano.

    Availability request

    • San Gimignano (Siena)
    • 18 km from Montespertoli

    Agriturismo la Lucciolaia

    In the vicinity of the medieval centre of San Gimignano, nestled in the rolling hills of the gorgeous Tuscan countryside, Agriturismo La Lucciolaia is perfectly located for exploring Tuscany's most prized art towns.
    This ancient farmhouse has been recently renovated and divided into eleven double rooms and two Suites, where the magic atmosphere of past times is perfectly blended with modern comforts.

    Availability request

    • San Gimignano (Siena)
    • 21 km from Montespertoli

    Agriturismo Villa il Palagetto

    Agriturismo Villa il Palagetto located in the vicinity of the medieval centre of San Gimignano, nestled in the rolling hills of the gorgeous Tuscan countryside.
    Provides comfortable accommodation in 6 double bedrooms and two Suites

    Availability request

    • Greve in Chianti (Florence)
    • 26 km from Montespertoli

    Villa Chianti 7 beds

    Villa Chianti is a private villa for rent in Chianti area with pool and garden that can accommodate up to 7 people.
    An oasis of peace and tranquility with views of the Chianti valleys not far from the main tourist attractions of Tuscany.

    Availability request

    • Colle Val D'Elsa (Siena)
    • 27 km from Montespertoli

    La Pieve

    La Pieve, charming farmhouse located on the hills of Val d'Elsa, between Volterra and San Gimignano, along the Via Francigena, in the heart of the Tuscan countryside, with its luxuriant nature and rich history.
    Framed by olive trees and a wood, it fosters a direct dialogue with nature in complete relaxation where they contemplate and enjoy the stillness in private and unique spaces.

    Availability request

    • Bagno a Ripoli (Florence)
    • 37 km from Montespertoli

    Villa Valdarno 12 beds

    Villa Valdarno is a typical Tuscan farmhouse located in a secluded and peaceful area in the heart of the Tuscan countryside, among vineyards and olive groves, and enjoys a privileged panoramic view of the Florentine Valdarno.
    The ideal solution for groups of friends or acquaintances who wish to spend their holidays in Tuscany with the comforts of a detached villa with swimming pool and large garden.

    Availability request

    • Siena (Siena)
    • 40 km from Montespertoli

    Agriturismo Marciano

    Agriturimo Marciano : an exlusive opportunity, two holidays at the place of only one. stay in the country and life downtown. Marciano is located near the walls of the Middle Age town of Siena.
    Five confortable double rooms and a suite with a beautiful sight on the Siena Duomo

    Availability request

    • Lucca (Lucca)
    • 51 km from Montespertoli

    Historic Villa Lucca 12 beds pool

    Historic villa 14 km from the center of Lucca immersed in the green of the Tuscan vineyards and olive groves, it has a private swimming pool and a large park.
    Set on 350 square meters in a dominant position offers a unique view of the hills of Tuscany.

    Availability request

    • Massarosa (Lucca)
    • 64 km from Montespertoli

    Stone Farmhouse Massarosa 8 beds pool

    Stone farmhouse in typical Tuscan style skilfully and elegantly renovated in a dominant position on the hills of Massarosa with spectacular views that reach the sea of Tuscany. The farmhouse has a swimming pool with whirlpool.
    Perfect solution for those that search the real authentic Tuscany staying in the hills but not far from the Versilia sea.

    Availability request

    • Viareggio (Lucca)
    • 66 km from Montespertoli

    Villa Torre del Lago 5 beds

    Typical Tuscan farmhouse for rent in Torre del Lago, Massaciuccoli area with 3 bedrooms and 5 beds, just 1 km from the Tuscany coast.
    Ideal solution for small groups or families looking for a villa for rent not far from the sea in a context of absolute privacy.

    Availability request

    • Massarosa (Lucca)
    • 67 km from Montespertoli

    Farmhouse Massarosa 14 beds pool

    Beautiful ancient Tuscan farmhouse completely renovated located on Tuscan hills 10 km from the golf course of Versilia. The villa can accommodate up to 14 people.
    An oasis of peace for those looking for a stay in the Tuscan hills while staying close to the sea. Perfect for a relaxing holiday in close contact with nature.

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    • Camaiore (Lucca)
    • 68 km from Montespertoli

    Charming villa Tuscany coast 14 beds pool

    Eighteenth-century villa located in a picturesque area of the Tuscan hills at the foot of the Apuan Alps, the villa has a park with swimming pool and tennis court.
    The spacious suites of the villa embellished with charming details and enhanced by modern comforts will make your stay an unforgettable experience.

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    • Camaiore (Lucca)
    • 68 km from Montespertoli

    Villa Pieve di Camaiore 8 beds pool

    Luxury and charming villa with swimming pool for rent surrounded by the green hills of Camaiore not far from the sea of the Tuscan coast.
    The villa is ideal for those looking for an oasis of absolute peace and relaxation guaranteed by the elevated position and the external fence in style.

    Availability request

    • Camaiore (Lucca)
    • 68 km from Montespertoli

    Villa Prato di Sopra Camaiore 10 beds pool

    This villa is really some thing special, perched on the top of a hill the views are endlessly breath taking.
    This villa is really some thing special, perched on the top of a hill the views are endlessly breath taking.

    Availability request