We'll meet you at the charming Corte del Sole country inn in Castiglione del Lago. Alla Corte del Sole is located close to Lake Trasimeno and also Montepulciano.

After the fitting of bikes you're free to explore the delightful hill town of Petrignano, which gazes down on tranquil Lake Trasimeno's fishing boats and beaches. Nearby Castiglione boasts a 16th-century town hall and a ruined medieval castle.
 

Today you will ride in the Chiana Valley, an easy ride until the climb to Cortona!

Explore this delightful hill town, made famous in the best-selling book Under The Tuscan Sun. Stroll its winding narrow- and steep -medieval streets, then enjoy a fabulous lunch at one of our recommended restaurants.

60km riding.

Today you ride from Petrignano to Pienza via Montepulciano, the jewel of southern Tuscany. En route you pause in the village of Monticchiello, the quintessential Tuscan hill town.

Your charming hotel Il Chiostro di Pienza is housed in a 15th century convent and sits protected and quiet right in the centre of this tiny town. It has been recently renovated but all the beamed ceilings frescoed walls and ancient tile floors have been preserved. It has a garden and swimming pool as well as wonderful views.

45km riding.

Today embark on a circular bike ride into the famed Orcia Valley.

Riding solely on country roads the first 15 km is downhill and very easy through gentle rolling hills. Then there is a gentle climb to reach Radicofani, an enchanting medieval village with a rocca (fortified stronghold) dating from 1200

After a stroll around the stately old town, you'll head back into the country, along some of those winding cypress-lined roads.

66km riding.

First pause in fairytale Bagno Vignoni, a miniature spa that is among the most unique towns in Europe, then push on to the monastery of Sant'Antimo, where you might catch one of several vesper services performed each day by the monks.

The famed wine town of Montalcino is your highlight: visit the fortress to see a breathtaking view of the entire valley you've just biked. Back in the saddle and enjoy the long downhill and flat stretch to reach San Giovanni and the charming castle that is your accommodation tonight.

La Locanda del Castello, built in limestone and bricks, is located in the old part of the small hamlet inside the walls surrounding the Castle of San Giovanni d'Asso, and which dates back to 1500.

(Note that there is a shorter option via San Quirico.)

55km riding.

Today you head to that Renaissance gem, Siena.

On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. Stop here to visit the beautiful buildings and perhaps have lunch at the restaurant.

Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands.

Your accommodation tonight is Il Chiostro del Carmine Residence, meticulously restored from a 14th century Carmelite Monastery. It is situated a few hundred metres from the Siena Cathedral and from Piazza del Campo.

40km riding.

End of tour after breakfast.