A Cicloposse representative will meet you at the charming Villa Marsili (you can arrive by the train to Cortona/Camucia station). After the bike fitting and orientation you're free to explore this delightful hill town, made famous by Frances Mayes in her best selling novel Under the Tuscan Sun, Stroll the winding narrow - and steep! -medieval streets, then enjoy a fabulous dinner at one of our recommended restaurants.

Accommodations: Villa Marsili in Cortona

Ride to Valle di Pierle and his splendid castle “Rocca”. The history of Val di Pierle is closely linked to the history of the splendid castle (la Rocca) that dominates the valley. The castle was built prior to the 10th century and belonged to the marquises of Monte Santa Maria Tiberina. Another climbs and reach the top of hill Cima di Tuoro from where you will be able to enjoy a stunning view of the Lake and its islands From the top enjoy the nice downhill to Tuoro sul Trasimeno. You are in Umbria region now. in Tuoro you can stop in the village at the beach.On the saddle again and back to Cortona on gentle terrain with last climb to Cortona.

Total distance: 50 km / 31 miles
Elevation gain: + 164 ft / - 164 ft | +1042 m / -1038 m
Accommodations: Villa Marsili in Cortona
Meals: Breakfast

Ride from Cortona to Pienza via Montepulciano, through vineyards. This splendid little town – whose artistic and architectural heritage led it to be called the Pearl of the Cinquecento – has preserved its beauty intact. Leave the hilltown taking soon a beautiful scenery back road leading you to Monticchiello: you are now at one door to Parco naturale e artistico della val d’Orcia, it is an UNESCO site with this main justification: “The Val d’Orcia is an exceptional reflection of the way the landscape was re-written in Renaissance times to reflect the ideals of good governance and to create an aesthetically pleasing picture.” Imagine cycling up and down in a scene from painting to get to the perfect Renaissance town Pienza, now famous also for the delicious sheep milk cheese: “pecorino”.

Total distance: 39 mi / 63 km
Elevation gain: +3441 ft / -3350 ft | +1049 m / -1021 m
Accommodations: Hotel Il Chiostro in Pienza
Meals: Breakfast

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, you'll head back into the country, along some of those winding cypress-lined roads and stop in another medieval village Contignano. Have a light lunch to stoke your legs and back in he saddle take another scenery road back.

Total distance: 39 mi / 63 km
Elevation gain: +3349 ft / -3380 ft | +1022 m / -1029 m
Accommodations: Hotel Il Chiostro in Pienza
Meals: Breakfast

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.

Total distance 28 mi / 44 km
Elevation gain: +3021 ft / -2874 ft | +920 m / -876 m
Accommodations: Hotel Vecchia Oliviera in Montalcino
Meals: Breakfast

Bike ride from Montalcino to Siena via Monte oliveto Maggiore and Asciano. On the way you'll coast along the forested crest of a ridge, home to the famed Monte Oliveto Maggiore monastery. visit the beautiful buildings and admire frescos. Afterwards, you'll travel through the fascinating area called Le Crete, Tuscany's answer to the Badlands. Often described as Italy's best preserved medieval city, Siena rivaled Florence for dominance in Tuscany during the 1300s. leisurely stroll about this medieval art city in the afternoon and to visit Piazza del Campo square, Torre del Mangia and the famous Duomo. The main square is famous because here it is held twice a year the disputed “Palio” horse race, which opposes the 17 “contrade” of this fascinating city.

Total distance 36 mi / 58.7 km
Elevation gain: +3396 ft / -3995 ft | +1035 m / -1217 m
Accommodations: Hotel Villa STR in Siena
Meals: Breakfast

Your tour ends in Siena after breakfast. Extend your stay with an additonal day or two to explore the city or continue on to parts of Tuscany. Nearest airport is Florence, airport transfer available (additional costs apply).

Meals: Breakfast