Italian Classic: The best of Tuscany

Once you’ve arrived, our staff will be waiting to welcome you to Siena. They will give you a briefing on the week ahead and help you assemble and prepare your bikes for our first ride on Day 2. We will enjoy a welcome drink together before having dinner at Monteriggioni Castle. We will spend the night at Sangallo Park Hotel.

To kick off our tour, we’ll be riding through the extraordinary Chianti Hills area, famous around the world for the excellent Chianti wine grown on the land. We’ll set out directly from the hotel in Siena and head to Gaiole in Chianti. We’ll ride across the rolling hills surrounded by vineyards, deep in the enchanting landscape. Our next stop will be Radda in Chianti, where we’ll stop for a coffee and ice cream in the magnificent old square. Just a few kilometres left before heading back to the hotel where we can relax in the swimming pool and get freshed up ready for our delicious dinner in Siena. We will spend the night once again at Sangallo Park Hotel.

We will start the day with a hearty breakfast before setting off on our bikes towards Monteroni D’Arbia on quiet country roads through the magnificent Val d’Arbia. We will ride towards Asciano, with its splendid Monte Oliveto Maggiore abbey towards our next destination, Buonconvento, in the Ombrone valley. Our final stretch takes us to today’s destination: Montalcino. Our charming accommodation, an excellent dinner made from local ingredients and a glass of fine wine await us as we bring our second day of riding to a close. We will spend the night at the Hotel dei Capitani.

Another memorable ride awaits us on Day 4. Today we’ll discover the unique Val D’Orcia, riding on peaceful country roads. Our day begins by descending from Montlcino to Torrenieri, before we ride over rolling hills and through ancient villages, where we’ll inevitably stop for a morning espresso. We will then visit the splendid San Quirico d’Orcia for lunch in a typical “trattoria” to refuel ready to take on the demanding Montalcino ascent. This ascent is 10 km long with 500 m of positive elevation. A wonderful dinner in this fairy-tale village will bring our fifth day to a close, before we spend the night once again at the Hotel dei Capitani.

Our route on Day 5 offers another superb experience riding through mediaeval villages surrounded by stunning nature. San Quirico d’Orcia is the first village we come to. Radicofani, a wonderful village dominated by a castle, is waiting for us next along our route. Finally, we will cross over into the region of Lazio at Acquapendente, where we will be justly rewarded for our efforts with a visit to the historical centre and an excellent dinner. We will spend the night at Sant Apollinare Farmhouse.

On the cards today for our final ride is a change of scenery. We will start by riding back, briefly, into the Tuscany region to Pitigliano, with its characteristic historical centre called “Little Jerusalem”, due to the presence of an ancient Jewish community. After leaving Pitigliano we will set out towards Lake Bolsena, a destination that coincides with our return to the Lazio region, where 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 final dinner. We will spend the night at the Hotel Royal.

We will enjoy a final breakfast together as a group at the hotel before catching our transfer back to Siena and heading off on our respective onward journeys.