From Piazza della Signoria to Piazza del Campo, this trek joins two of the most important Tuscan cities in terms of history and art. Florence, the city of Leonardo, Giotto, Dante and Brunelleschi, and Siena, home to the "Palio". What these two jewels have in common is that are located in one of the most famous areas in Tuscany - "the wine road". Leaving Radda in Chianti, the route cross this famous area, walking along paths and roads surrounded by vineyards and olive groves. The typical Chianti landscape is hilly, varied and colourful and it is here where the famous wine - produced since the time of the Etruscans - was born. The last part of the trek takes you to Colle Val d' Elsa, a lovely medieval village and then, along the Via Francigena, up to Saint Gimignano. The latter's hill has an unmistakable shape and dominates the beautiful surrounding landscape.

Highlights:
- The superb art towns of Florence and Siena
- San Gimignano, Colle Val d'Elsa and Monteriggioni: medieval jewels of Tuscany
- The Chianti region: the territory of wine, art and history

Daily itinerary
Day 1: Arrival in Florence Individual arrival in Florence. Meeting with the Guide at the hotel in the afternoon. Dinner in a typical restaurant and overnight in hotel***. Meals (-/-/D).

Day 2: Florence and the sunset of San Gimignano (2hrs 30min walking, +150m – 150m)
After breakfast, visit of the historical centre of Florence whit a touristic guide, from the Cathedral of Santa Maria del Fiore to the Baptistery of S. Giovanni and the amazing Palazzo della Signoria. Transfer by public bus (1hr 30min) to S. Gimignano (bringing your luggage with you). San Gimignano is known as the "New York" of the Middle Ages, due to its several towers surrounding the historical centre. The village is considered across the world to be one of the best examples of medieval architecture in Italy. A gentle walk in the fields and vineyards will allow us to admire the sunset over the towers of the town. Dinner and overnight in Hotel*** in S. Gimignano. Meals (B/L/D)
Day 3: San Gimignano and the countryside (4hrs walking, +350m – 350m)
Today we discover the amazing landscape that surrounds S. Gimignano. Following ancient paths and typical "white roads", our walk leads us past quaint Romanic churches and chapels, lush forests of chestnut and spectacular fields and vineyards. The wild boar, the noble pheasant and the roe, inhabit this area, close to small villages built with local stone and wood. At the end of the hike, you will be treated to a special olive oil tasting. Olive oil is one of the specialities of Tuscany, famous globally. Dinner is not included. Overnight in Hotel*** in S. Gimignano. Meals (B/L/-)

Day 4: The Via Francigena to Colle Val D'Elsa (4hrs walking, +370m -310m)
The Via Francigena is a journey steeped in history, an ancient path which led from Canterbury to Rome, travelled by thousands of pilgrims in the past. A gentle hilly trail will take us to Colle Val d'Elsa, an interesting town located in the heart of Tuscany, in a strategic position, close to the cities of Siena, Florence and Volterra. The main activity of Colle Val D'Elsa, described as "the Bohemia of Italy", is the manufacture of glass and the production of lead-crystal glass. Private transfer (30min) to Radda in Chianti, the heart of the superb Chianti wine region. Dinner and overnight stay in Radda in Chinati. Wine tasting and organic food for dinner. Meals (B/L/D)

Day 5:The Chianti Region (4hrs walking, +400m -400m)
"Chianti" is a land of ancient winemaking traditions practiced by both the Etruscans and Romans. The first documents identifying an area (and the wine) of ​​Chianti where wine was produced date back to the thirteenth century, and refer to the Chianti League founded in Florence. Starting from our Agriturismo, a circular hike will pass through ancient vineyards and the panoramic hamlet of Volpaia. Dinner and overnight stay in Agriturismo in Radda in Chianti. Meals (B/L/D)

Day 6:Towards Castellina in Chianti (4hrs walking, +440m -500m)
Another wonderful day in the heart of the Chianti Region. After breakfast, a beautiful hike towards the stunning medieval town of Castellina in Chianti, located amongst vineyards and olive trees. At the end of the walk, short transfer to the Agriturismo. Before dinner, wine tasting of the typical Chianti wines. Dinner and overnight stay in Agriturismo in Radda in Chianti. Meals (B/L/D)

Day 7: From Monteriggioni to Piazza del Campo, Siena (5hrs walking, +350m – 300m)
After breakfast, short transfer (30min) to Monteriggioni. This village, with its walls and 14 towers perfectly preserved, dominates the countryside from the top of the hill. Following the ancient Via Francigena again, this last section of our trip is considered one of the best countryside hikes in Italy. The arrival as a "pilgrim" in Piazza del Campo in Siena, is just unforgettable. Dinner and overnight stay in Hotel *** in Siena. Meals (B/L/D)
Day 8: Siena
After breakfast, depending on your departure time, free time to discover the historical centre of Siena. End of services and individual departure. Meals (B/-/-)  





Note: B (Breakfast); L (lunch); D (dinner)