Arrive into Pisa or Florence and we will pick you up from the airport.
Today you will ride out into the lush Chianti countryside. Your ride will take you to the beautiful town of Strada in Chianti and as you head further south, you will notice the air changing, the smell of grapes drifting through the breeze and be greeted with miles and miles of vineyards. Stop in Greve in Chianti to discover the local town square, or should we say triangle, and enjoy a coffee. To blend in, remember cappuccino is a morning drink in Italy and not to be drunk after lunch!
From Greve you will head towards Panzano, a medieval town that has been fought over by Siena and Florence for hundreds of years. If you are riding this route on a Sunday, the town has a morning outdoor market selling cheeses, meats, flowers and other Chianti favourites. From Panzano you will ride back to the hotel.
Leave your bags for collection in the morning and ride out today on our favourite Tuscan route. The morning will take you up some hills for about 10km before a long downhill through San Benedetto. Then it’s a climb to San Giminano, a sight for any seasoned traveller, and a UNESCO World Heritage Sight. Encircled by its medieval walls and with its hilltop views, 12th century skyscrapers loom over the Piazza della Cisterna. We recommend a plate of Pappardelle, a favourite in Tuscany, in one of the numerous restaurants and cafes in the town.
From there, the route heads back out into the countryside finishing with a bit of climbing up to your hotel for the evening.
You can leave your bags at the hotel as you will be returning there at the end of the day. Today’s route is a beautiful loop taking in some climbing and some downhills through this undulating and hilly countryside.
You will pass through Radda in Chianti, a beautiful medieval town, perched on a hill with stunning views. From there, it’s on to Gaiole in Chianti, famous for it’s green gold olive oil. Deep tasting, spicy and peppery olive oil, is a feature of Chianti and you will notice colour and texture changes as you ride through the region.
The route takes you past Castello di Brolio where Baron Bettino Ricasoli invented the Chianti formula in 1872 so feel free to stop and explore the castle. From there, it’s back through the Cypress tree lined roads to the hotel.
You can leave your bags in the hotel as we will be returning later in the evening. Today’s ride takes us on a loop and into Siena, a UNESCO World Heritage Site. The Piazza del Campo is the highlight with it’s open square featuring the Mangia Tower.
The city will be flying the flags of the local contrade, or city ward and the right to fly the flag is won and lost in an epic biannual horse race known as the Palio di Siena. The horse race has been run since the 14th century and the Piazza del Campo is turned from a square with people milling about, to a horse track featuring bareback riders being thrown from their mounts in ever tightening turns. If you happen to be in Siena on 2 July and 16 August, this is one of the most thrilling Tuscan experiences.
Leave a bit in the legs as the ride back to the hotel is mainly uphill.
Enjoy a leisurely breakfast at the hotel and you will be transferred back to the airport for your return flight home.
If there is a better cycling experience than riding through Tuscany then we haven’t found it yet. Explore the medieval fortified towns of San Giminano and Montepulciano, sip cappuccino in a Chianti town square and roll through the endless olive groves and vineyards.
Cypress trees will line your routes and under the warm Tuscan sunshine life’s daily stresses just melt away.