• Distance: 73 km45 mi
•  Elevation: 1150 m3773 ft

Our first contact with this extraordinary region takes place in the Chianti Hills area. This area, famous all over the world, gives the name to the excellent Chianti wine. We’ll start our cycling day directly from our Hotel in Siena and heading to Gaiole in Chianti, we’ll ride through these rolling hills, surrounded by vineyards deep in an enchanting landscape.

Once we arrive in Radda in Chianti we’ll stop for a cappuccino and cornetto in its magnificent old square.
After our stop, we’ll keep on riding up and down, enjoying breathtaking views of vineyards and wild areas and going through historic villages. Getting to the Hotel, we can wind down in its swimming pool and get ready for our delicious dinner in Siena.

Overnight in Siena.

• Distance: 72 km45 mi
•  Elevation: 1200 m3937 ft

After an excellent breakfast, departure towards Monteroni D’Arbia on quieter secondary roads, through the magnificent Val d’Arbia. We will then continue towards Asciano, with its splendid Monte Oliveto Maggiore abbey. Riding up and down between hills and cypress trees you will arrive at Buonconvento, in the Ombrone valley.

The final stretch of the day’s ride takes us to our destination today: Montalcino. This town is well-known for the production of the famous Brunello wine, which you may be interested to know is never sold less than five years after the grape harvest, and becomes “Reserve” after at least six years . Welcoming accommodation and an excellent dinner of local food and fine wine bring this first day by bike to an end.

Overnight in Montalcino.

• Distance: 68 km42 mi
•  Elevation: 1000 m3281 ft

A new unforgettable day is waiting for us. Today we’ll get in touch with the unique Val D’Orcia, riding on peaceful back roads. We’ll start our day dealing with the descent from Montlcino to Torrenieri, then we ride continuously up and down through ancient villages, where we’ll have our inevitable cappuccino and espresso.

Then, we must absolutely visit the splendid Pienza, where we can have lunch in a typical “trattoria” to recover energy for taking on the demanding Montalcino ascent. This ascent is 10 km long with a difference in altitude of 500m. An exclusive dinner in this fairy-tale village will close our fourth day.

Overnight in Montalcino.

• Distance: 76 km47 mi
•  Elevation: 1200 m3937 ft

Another superb day through villages surrounded by breathtaking nature. San Quirico d’Orcia is the first village we encounter, the spa in its hamlet Bagno Vignoni is famous. Radicofani, a wonderful village dominated by a castle, is waiting for us along the way. Finally, we ride into the Lazio region at Acquapendente, where we will be justly rewarded for our efforts with a visit of the historical centre and an excellent dinner.

Overnight at Sant Apollinare Farmhouse.

• Distance: 61 km38 mi
•  Elevation: 700 m2296 ft

A change of scenery is the main feature of today’s ride: we ride back, briefly, into the Tuscany region and arrive in Pitigliano, with its characteristic historical center called “Little Jerusalem” because of the presence of an ancient Jewish community.

After leaving Pitigliano we head for Lake Bolsena, a destination that coincides with our return to the Lazio region, Civita di Bagnoregio is waiting for us. Here, a very different landscape will provide the ideal setting for an evening in good company and a delicious dinner.

Overnight in Bolsena.