Montecarlo is situated at the base of an ancient fortress occupying the summit of the ridge separating the Valley of the Nievole from the Plain of Lucca. The community was a redoubt of the Ghibellines in their perpetual struggle with Florence and the other Guelf communities. The hilltop town of Montecarlo is situated west of Florence in the northwest part of Italy's tuscany region.

History
Prior to 1333, the year in which the walled town of Montecarlo with its Rocca was founded, on this hill was sited the Del Cerruglio fortress and it formed part of the fortifications of the nearby Castle of Vivinaia, now disappeared. Several documents record the Cerruglio fortress as being 'a badly aligned gothic building surrounded by mighty walls erected with squared masonry stones and protected by a fortress with keep and towers'.
The path that lead to the main gate.
During the fourteenth century the fortress played a strategic role in the wars between Lucca, Pisa and Florence and was from its walls that Castruccio Castracani, lord of Lucca, directed the movements of his army which helped him to win the battle of Altopascio in 1325. Ruins of the old fortress can still be identified in the northwest section at the highest vertex of the triangular shaped defense perimeter, delimited by an imposing round tower, still crenelated, connected with the other two corners through powerful curtains built in bricks and endowed with a quadrangular tower in the middle. Also the main front toward the city is built in bricks, with a semicircular tower and double walled curtain: the external one with battlements and the inner one equipped with machicolations on stone brackets.
The northeast front of the town walls.
The main gate on this side can be reached only walking through a tight path, whose walls are equipped with machicolations and gun holes too. The fortress was renovated and enlarged by Carlo IV and afterwards by Cosimo I de' Medici in the sixteenth century with the addition of two bastions (never completed) on the eastern front, in order to create a great courtyard for the Valdinievole's Army. In 1775 fortress was dismantled and now it is a private property visible only from the outside.
The rocca is connected with the town walls, which even today remains fairly intact, even if only a few of the 15 original towers remains. The Northeast side is naturally well defended and it was built without towers. Three town gates are well preserved: the Florentine Gate and the smaller Lucca Gate were built in the 14th century, the Porta Nuova (New Gate) is of the 16th century.

THE THEATRE OF THE RASSICURATI The history of this theatre is linked to that of the Academia of the Assicurati which held the theatre until 1966. The Academy was founded in 1702 by 19 notables. Count Murzio gave his house to the Academy and fifty years later it was possible to have the firts theatre. All through XIX century the theatre was particularly active. It was enlarged in 1894.

THE WALLS AND THE GATES The walls date back to 1333 where the town was founded. There are four main gates: Porta Fiorentina - As part of the walls this gare dates back to the XVI century. Porta Nuova - Its name is due to the fact that the gate was reopened and lifted in 1598. Porta a Lucca - It has smaller dimensions than the others and it was rebuilt and enlarged between 1570 and 1594. Porta a Pescia It was closed during the XVI century when the Medici began the construction of the fortress.

The wine
Although the town was founded for warlike purposes, it is an oasis of tranquillity, with vast expanses of vineyards and olive orchards extending outward from the town as far as the eye can see. Those vineyards are the source of Montecarlo wine.
The wine originated in the Roman period and its fine quality was cited in documents drawn up in the centuries preceding the year 1000.
The vinicultural industry was already flourishing before the period of the communes and the wines of Montecarlo were the most expensive of the region. At Florence, the principal consumer of the town's output, Montecarlo cost more than the Trebbianos, the whites of the Chianti area and the wines of the Greve Valley. In the 15th century, the wine was highly appreciated by Pope Paul III Farnese, according to a document written by his cellarmaster. The wine had already pleased the palate of a preceding pontiff, Gregory XII, who visited the area in 1408. A member of the pope's train, Cardinal Giovanni Dominici di San Sisto of Ragusa, enjoyed the reputation of being a fine connoisseur and devoted consumer of wine. During the visit, the cardinal so much appreciated the wine that was served to him in large quantity that he forgot his episcopal ring, leaving it behind on the banquet table.
The wine of Montecarlo remains true to its history since it is generally considered one of the enological treasures of Tuscany. Montecarlo DOC makes only a bianco and a rosso, the former with the best reputation. The white wine uses mainly trebbiano, but a host of other grapes are allowed-Pinot Bianco (pinot blanc), Pinot Grigio (pinot gris), roussanne, Sauvignon (sauvignon blanc), sémillon, and vermentino. The red wine uses from 50 to 75 percent sangiovese, plus canaiolo, Cilegiolo, Colorino, malvasia, and syrah. visit the wine roads of Montecarlo hills

The Montecarlo Farms Visit to some of the outstanding wine-producing farms placed on the slopes of the picturesque fortified village of Montecarlo, passing through the enchanted woods of the "magic ancient Vivinaia".

How to reach montecarlo
Montecarlo is easily reachable from Florence following the A11 Firenze-Mare until the exit 'Altopascio' and then following the signals.