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email The cloister  of Monte Oliveto Maggiore houses 15th and 16th century frescoes featuring the Life of St. Benedict painted by Luca Signorelli and il Sodoma which are today considered to be some of the most important Renaissance artworks in Italy.

Italy Experiences

“Under the Tuscan Sun”


Cortona~ Montepulciano ~ Siena

tribally Self Guided, 7 Days/ 6 Nights, Euro 1,350 per person sharing

Starting from Cortona on the border of Umbria andTuscany, this tour will offer you the chance to discover Montepulciano, Pienza, Montalcino and the  val d’orcia Le crete area through a landscape of sculpted curves created over the centuries by natural and man made forces. 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. Your tour ends in Siena a medieval city with beautifully preserved Gothic architecture, with the famous Piazza del Campo where the “Palio” horse race takes place.

Day 1:Cortona Etruscan town
Meet at the charming Villa Marsili. After your bike fitting and orientation you’re free to explore Cortona, a delightful medieval hill town, made famous by Frances Mayes in her bestselling novel “Under the Tuscan Sun”.

Day 2: Lake Trasimeno
Your bike tour starts with a downhill ride from Cortona to Valle di Pierle. Following this continue on to the top of hill Cima di Tuoro from where you will enjoy a stunning view of the Lake and its islands. After a ride to Tuoro sul Trasimeno  you will have entered the Umbria region before returning to Cortona Distance 52km/32,5Miles.

Day 3: Montepulciano & Pienza
Ride through vineyards from Cortona to Pienza via Montepulciano. 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 hill town taking  the scenic back road leading you to Monticchiello: you are now at one door to Parco della val d’Orcia, a UNESCO world heritage site. Finally cycle on to the famous Renaissance town Pienza, now famous also for the delicious sheep milk cheese: “pecorino”. Distance 55km/34miles.

Day 4: Val d’Orcia and Radicofani
Today take a looped bike tour into a UNESCO site park,  through gentle rolling hills and climb to Radicofani, an enchanting medeival village with a 12th century Rocca or castle. Once you have finished exploring, head back into the country, cycling along winding cypress-lined roads before stopping in another medieval village – Contignano. Distance 66Km / 40,5Miles

Day 5: Montalcino & Brunello wine
The first pause of your bike trip today is in fairy-talesque Bagno Vignoni, a miniature spa town, before pushing on to the monastery of Sant’Antimo, where you might catch one of several vesper services performed by the monks. The famed wine producing town of Montalcino is also a highlight today: visit the fortress to see a breathtaking view of the entire valley you’ve just biked. Distance 46 km/28,5 Miles 

Day 6: Monte Oliveto and Siena
Today’s bike tour  from Montalcino to Siena will take you via Monte Oliveto Maggiore, a benedictine abbey famous for its frescos. Afterwards, travel through the fascinating area of Le Crete, Tuscany’s answer to the Badlands. Today’s highlight is Siena, with its Piazza del Campo square, Torre del Mangia & famous Duomo. Distance 58Km / 37,5Miles 

Day 7: Sightseeing in Siena
Enjoy your farewell breakfast marking the end of your bike tour: Arrivederci!



What’s Included?

Included in this trip:

Six nights in excellent four & three-star hotels
Six breakfasts
Route notes, maps, elevation gain and city map
Sightseeing, restaurant and shopping suggestions
All Baggage transfers
Delivery bike & equipment in Cortona
Pick-up of bikes and gear in Siena
Keepsake Cicloposse water bottle
Sales taxes


What’s not included?

Airfare to Italy, Lunches and dinners, alcoholic/non-alcoholic beverages, gratuities, travel insurance, laundry expenses and items of a personal nature.

Dates and Pricing

Cost: Euro 1,350 per person (in double occupancy)
single supplement euro 350

Optional luxury hotel upgrade la Bandita on day three & four
Cost: Euro 1,550 per person (in double occupancy)

Hybrid/Touring bike  euro 140
High-end Race bike euro 170

Helpful Notes

Daily Mileage and Difficulty: 30-35 miles per day on gently rolling terrain with some climbs. This tour can be tailored to include longer rides on request.

Tour Departures: Any date between 15th March to end of October.

Length: This tour is 6 nights long but is possible book the first 4 days only or to add some days or legs.