The village of Montefioralle between history and wine

Montefioralle, Greve in Chianti


Min. 2persons

Write to

+39 339 863 60 36


Min. 2persons

Distance: 5Km

Elevation gain: 250Mt

Duration: 2hours - Including breaks

Technical Difficulty: E - Hiking

Physical Effort: Easy

Hike and tasting in the village of Montefioralle in Chianti

It was the year 1000… it seems the beginning of a legend with knights, duels and fortresses in the heart of Chianti.. Certainly the history of the castle of Montefioralle has the same charm of a fairy tale, because in those years starts the construction of a small fortified monastery on the top of the hill called Montefioralle (originally Monteficalle). Little by little, the village begins to be populated with small houses and, over the centuries, the settlement grows and is embellished, also thanks to some rich noble Tuscan families who settle there: the Ricasoli, the Benci, the Gerardini and the Buondelmonti.

The village slowly takes on the appearance of a real castle. The final transformation is accomplished by Castruccio Castracani, famous leader and Lord of Lucca, who in 1325 takes the fortified abbey by force and enlarges its structure with towers and walls, making it one of the most imposing castles of Chianti. Thanks to its strategic position, the village of Montefioralle,which still dominates the Val di Greve and the ridge of the Chianti Mountains, increases its prestige and power, and in the fifteenth century, under the dominion of the Republic of Florence, becomes the most important military and administrative center of the entire area. Do you want to know more about the history of Chianti? Discover other stories here .

Our hike to Montefioralle in Chianti, along the gentle hills characteristic of the areawill take us to admire the splendor of this village through picturesque views of rare beauty, “decorated” by woods on the summit, vineyards and farmers’ houses scattered in the estates. The hike will lead us inside a family-run winery (the smallest of the area) which, thanks to only 5 hectares of certified organic vineyards, produces wines of extraordinary elegance.

We will then relax by tasting their flagship wines, among which the organic Chianti Classico, together with small local gastronomic delights, all while enjoying the spectacular view of Montefioralle, included in the list of the most beautiful villages of Italy.

Required equipment


Closed hiking boots




Adequate water supply



The village of Montefioralle between history and wine

Start your experience

The village of Montefioralle between history and wine


Min. 2persons

The guide reserves the right to adjust times and itineraries in case of unfavorable weather or particular needs of the hiking group.

Coordinated and assisted by a licensed Environmental Hiking Guide (Regional Law 86/2016, as amended)

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Walking, discovering, and tasting

This is WeHike

In the heart of Tuscany WeHike accompanies you on daily hiking in Chianti combined with original experiences to search for artistic, wine, gastronomic, and artisanal treasures.

We walk to come into contact with this region’s nature: the hills, the streams, the woods, the trails through vineyards, and the wildest corners. We discover history, traditions and hidden gems of Chianti region: old farmhouses, parish churches, castles, and workshops where craftsmen create as they did once upon a time.  Learn the stories and legends.

We taste the fruits of this land: tasting chianti wines together with traditional dishes, savoring the scents of flowers, observe the colors of the fields and hear the sounds of every environment we pass through.

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