Starting from Lake Trasimeno on the border Umbria/Tuscany you will discover Cortona, Montepulciano, Pienza & val d'orcia; le crete area through a landscape of sculpted curves designed over the centuries by wind, rain, and man. The mystique of this land lies not only in its landscape, but also in its nature, its vineyards and its history: oak woods, olive groves and vineyards watch over enchanting hillsides, medieval villages and historical monuments. Glorious ending in Siena


Day One - Castiglione del Lago
We'll meet you at charming Corte del sole country inn (you will arrive by the train to Chiusi-Chianciano station, a major stop on all the Rome-Florence lines) After the fitting of bikes you're free to explore this delightful hill town, which gazes down on tranquil Lake Trasimeno's fishing boats and beaches. Castiglione boasts a 16th-century Town Hall and a ruined medieval castle.
Lodging at Corte del Sole in Petrignano


Day two: Cortona
Total distance: 60 km.
Today you will ride in the Chiana valley, will be easy until the climb to Cortona! explore this delightful hill town, made famous in the best-selling book Under The Tuscan Sun. Stroll the winding narrow - and steep! - medieval streets, then enjoy a fabulous lunch at one of our recommended restaurants.
Lodging: hotel Alla Corte del sole in Petrignano


Day three: Pienza & Montepulciano
Total distance: 45 km.
Ride from Petrignano to Pienza via Montepulciano, the jewel of southern Tuscany and a stop in the village of Monticchiello, the quintessential Tuscan hill town. Your charming hotel Il Chiostro is housed in a 15th-century convent in a quiet, secluded location right in the center of Pienza - itself is a rare masterpiece: entirely rebuilt between 1459 and 1462, it was the brainstorm of Pope Pius II.
Lodging hotel Il chiostro


Day four: val d'orcia & Radicofani
Total distance: 66 km.
Circular bike ride into Orcia valley: is a completely country ride and for the first 15 km you will ride downhill and very easy gentle rolling hills. Then the gentle climb to reach Radicofani, a medieval and enchanting village with a 1200 dating Rocca. After a stroll around the stately old town, we'll head back into the country, along some of those winding cypress-lined roads.
Lodging hotel Il chiostro


Day five Montalcino & San Giovanni d'Asso
Total distance: 55 km.
first pause in fairy-tale 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 part to reach San Giovanni and the charming castle that is your accommodation.
Shorter option via San Quirico.
Lodging hotel locanda del castello


Day six - siena
Total distance km 40
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.
Lodging hotel Il Chiostro del Carmine


Day seven end of tour after brekfast