Walking tour:
Pristine charm of Chianti
One of the most famous and best loved regions of Tuscany, Chianti is as rich in history and culture as it is in wine and olive oil. Stretching from Florence to Siena, its rolling landscape offers breathtaking vistas on rows of vineyards, woods and fields dotted by medieval castles, pristine fortified towns, important monasteries and churches.
Our itinerary of trails and dirt roads offers the chance to live out a slow-speed adventure on foot: you will explore the Chianti most secluded spots and appreciate its unique charm.
Starting from Siena we’ll encircle the beautiful Chianti countryside with its breathtaking sceneries that we have come to know and love so much and complete our tour by walking along waves of clay in the “Crete”, through a landscape of sculpted curves designed over the centuries by wind, rain, and mantified towns, important monasteries and churches
Itinerary:
Day one – Welcome to TuscanyArrival of the tour participants in
Siena. Check in our hotel Palazzo Ravizza, a charming hotel in a 15th century historical building in the center of town. Briefing meeting with your guides. Welcome Dinner.
Day two –Siena & “Chianti Classico” regionOur day will start with a guided tour of Siena historical and artistic treasures, including the world-famous main square del Campo, with its unique semicircular inclined outline. After lunch, we will transfer to Casstellina in Chianti: the town still preserves the medieval layout of a Florentine fortified hamlet, with its quadrangular circuit of walls and its Fortress, a 15th century building with an impressive crenellated coping tower. The village is surrounded by charming farmhouses, little Romanesque churches and the remains of fortifications. We will walk through the woods to visit the grandiose ruins of a castle once of strategic importance. Before dinner, you'll have time to stroll among late-Renaissance mansions in the central Via Ferruccio, or “underground”, along the picturesque Via delle Volte, a completely roofed street originated by the dwellings built up against the walls.
Lodging hotel Palazzo Squarcialupi Day three –
The Florentine Chianti treasuresToday’s tour will take us towards the northern boundary of the Chianti region, Our walk starts from
Panzano, an ancient town which has preserved its old walls, gate and the keep of the medieval castle, to reach
Greve in Chianti. Once the commercial center of the various regions of Chianti, Greve is arranged around a spacious triangular square surrounded by deep arcades still used for trading and by a church, Santa Croce, which contains interesting 14th century paintings. We will then continue until
Montefioralle, a beautiful walled village characterized by its steep narrow cobblestone streets. Our final destination is
Badia di Passignano, the religious complex that boasts the highest number of art works in the whole Chianti. Back to Castellina, we'll take the opportunity to taste some of the great wines which have made the Chianti one of the most renowned regions in the world.
Lodging hotel Palazzo Squarcialupi
Day four - Exploring the Chianti smooth hills and woodlands
Our walks encircle the beautiful Chianti countryside with its breathtaking sceneries that we have come to know and love so much. From the
castle of Brolio, the largest fortified residence in the whole Chianti as well as the headquarter of one of the leading wine-producing company of the world, we'll cut through dense woods overlooked by smooth hills scored by lines of vineyards to reach a small picturesque village. Here we’ll enjoy a typical Tuscan country lunch in a cozy trattoria. Then, after a good rest, we’ll end up our day with a touch of magic visiting the perfectly preserved citadel of
Monteriggioni, built by the Sienese in 1203 and made world famous by its circle of walls crowned with fourteen towers.
Lodging hotel Palazzo Squarcialupi
Day five – Discovering the magic medieval villages
Today’s walk will take us along the most renowned slopes in Chianti, from the country church of Santa Maria Novella to the tiny picturesque castle-town of
Volpaia. A famous wine shop is located in the keep of the castle, where different high-quality wines can be purchased, as well as red or white wine vinegar and extra virgin olive oil. After a deliciously reinvigorating Tuscan lunch in Carla’s garden (her ravioli and ribollita are well worth the walk!) and a rest, we will visit another charming village,
Radda in Chianti. Situated on a little hill Radda was made into a Florentine fortress during the 15th century and subsequently became chief town of the Chianti league. The ruins of the ancient defensive walls and look-out towers are all that remains of that period, along with the Palazzo Pretorio, which façade is still adorned with the coats of arms.
Lodging hotel Palazzo Squarcialupi Day six – From the wild Sienese Crete to AscianoOur last tour will lead us to the southern boundary of Siena territory, through the area of the Sienese Crete. Here the verdant hills of Chianti give way to little domes of clay and Tuscany reveals another facet of its identity, an unusual, almost lunar landscape of chalk cliffs and gullies soaked in a primeval atmosphere. We’ll walk along one of the most beautiful and suggestive unpaved roads in the region, among isolated farmhouses and breathtaking vistas of the most secluded area of the Crete. Picnic lunch at
Oliveto Maggiore Maggiora abbey. Founded in 14th century, this great monastery stands out in a beautiful position among lofty cypresses, and contains a large number of works of art, particularly in the loggia running around the larger cloister where the walls are frescoed with 36 scenes from the Stories of Saint Benedict. Transfer to
Asciano and check in the hotel CasaBianca, a 16th century villa situated high on the ridge that separates the Chiana valley. Farewell Dinner.Lodging Casa Bianca country inn
Day Seven – End of tour after breakfast.
Difficulty :
easy walk
Price :
Euro 2,200 p/person: based on double accommodation
Single supplement: Euro 300
Inclusions:
» Six nights in superior hotels with private bath and breakfast
» Six dinners (wine not included) & one wine tasting
» Five lunches (wine not included)
» Services of experienced bilingual local guides
» Support van, all transfer baggage
» Guided visit of historic sites in Siena
» Tickets for included visits
» All maps and trip notes
» Transfers from and to Siena or Chiusi rail stations.
Duration:7 days/6 nights
Dates:2010
13 - 19 September
Notes: Experienced local guides will lead our group, walking between 5 and 7 miles per day. A support van will escort us each day, to drive us around before and after the walks, as well as to welcome resting hikers. The groups are small (max. 12 walkers); to create a sense of intimacy.
Custom tour at anytime
ACCOMMODATIONS
Palazzo Ravizza is a renaissance Palace, which stands in a quiet area of the historical center of Siena. It was transformed into hotel in the 1920's and it has been recently renovated to offer modern facilities while maintaining original character. Lovely rooms and beautiful garden overlooking the Tuscan hills.
Palazzo Squarcialupi is part of the history of Castellina in Chianti. It is situated in the historical town center, on a road running along the XV century City Wall. It has medieval origins and it has been renewed becoming a luxury Palace with spa and beautiful pool overlooking the valley.

The estate of
CasaBianca is situated high on the ridge that separates the Chiana valley, and the famous "Crete Senesi”, in an area that is rich both in history and in natural beauty. The hotel is a villa of the 16th century has rooms furnished with antiques chosen with special care to the style and the epoch of the building.
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