Loc. Armaiolo, 64 - 53040 Rapolano Terme (SI) - Italia

“Crete Senesi” Tuscany bike tour

Crete Tuscany bike tour is an ideal option for cycling enthusiasts of all levels. Whether you’re looking to pedal calmly along the gentle lanes of this beautiful region, or to challenge yourself on the very same hills that cycling legends—including Bartali, Cipollini and Bettini have trained on, Tuscany can truly be said to be a land of cyclists, and much, much more. In the Crete Tuscany bike tour you’ll be able to enjoy a diverse array of Tuscany cycling routes. There are bike routes to the UNESCO World Heritage site Val d’Orcia, tracks across the stark but gentle landscape of Crete Senesi, or lanes cutting through the vineyards of Chianti and Montalcino. You’ll also get a chance to walk the hallowed halls where the Chianti wine was born, or to stroll in such renowned and beautiful towns as Siena and Pienza. You will be warmly welcomed for all 6 nights of your Crete Tuscany bike tour at LA CHIUSELLA, a family-run farm stay, or agriturismo. This is an excellent way to discover Tuscany at its most real and authentic. As well as being a working farm, LA CHIUESELLA has premium accommodation options with luxury trappings—perfect for couples, solo travelers, and families alike.

Ecological sensibilities are also fully respected on this greenest of Tuscan bike tour vacations. And a complete cultural immersion into the Tuscan lifestyle—together with a warm hospitality is guaranteed from Michele and Silva.


DAY 1: Asciano Warm-Up

Welcome to Tuscany! Our meeting point is at the Agriturismo LA CHIUSELLA in Rapolano Terme. We’ll get together at 12:30 pm in the Quadrifoglio reustourant for lunch and a brief introduction talk. In the afternoon after a bike fitting, we’ll ride around Asciano.

KM 28
mt 375 variazione di altitudine

DAY 2: Val Di Chiana

Today we’ll ride along the Val di Chiana reaching Cortona nice town famus for the movie “UNDER THE TUSCAN SUN”. The Val di Chiana is a huge fertile plain bordering Lazio, Umbria and Tuscany. It has an esteemed agricultural production, becoming the symbol of the Terre di Siena and of entire region.

KM 106
mt 1268 variazione di altitudine

DAY 3: Val D’Orica

Today we’ll plunge into Val d’Orcia, considered one of Italy’s wonders and a UNESCO World Heritage Site. Medieval castles, sunny rolling hills, isolated hill top towns, charming isolated rural homes, avenues of cypresses, and golden wheat fields are just some of the elements of the fantastic and harmonious landscapes of this area. We’ll stop in Pienza, another UNESCO World Heritage site, for a stroll through town.

KM 93
mt 1581 variazione di altitudine

DAY 4: Rapolano Terme, Siena and Crete Senesi Loop

Today is a rest day! There will be an optional loop ride along the Crete Senesi, the world’s most photographed panorama! For those who don’t want to ride, spend the morning at the Spa and natural hot spring San Giovanni in Rapolano Terme. Hot springs are naturally produced by the emergence of geothermal heated groundwater from the earth’s crust. The Terme di San Giovanni is a natural terrace overlooking the sea of hills that is the Crete Senesi, so while relaxing in the pools or having lunch, you can enjoy a breathtaking view on this gorgeous landscape.

KM 73
mt 1408 variazione di altitudine

DAY 5: Chianti Classico

Today we’ll ride through the famous Chianti Classico region. We’ll ride along Castello di Brolio, built around 1,000 AD and owned since 1141 by the Ricasoli family, the oldest winery in Italy and the second oldest in the world. Afterwards, we’ll stop for lunch in Gaiole in Chianti, the starting point of L’Eroica, and we’ll visit the vintage “White Roads” to browse a selection of artisanal products. In the late afternoon, we’ll return to LA CHIUSELLA we can enjoi the olive test.

KM 95
mt 2071 variazione di altitudine

DAY 6: Montalcino

Our last ride will lead you to Montalcino, the city of the famous wine Brunello di Montalcino DOCG. We will ride along the Pecorile road in the heart of Crete Senesi and the Asso Valley. Montalcino, renowned all over the world for the production of its precious Brunello red wine, has scarcely changed in appearance since the 16th century. Once you get up to the town, a magnificent spectacle unfolds for your eyes.

KM 91
mt 1506 variazione di altitudine

DAY 7: Monte San Savino

Today will have a short ride to Monte San Savino was one of the first urban settlements
in Tuscany, Italy. It originated around 1100, but a further century had to pass before Monte San Savino could be considered a centre of a certain social, political and cultural importance of Tuscany in those times. But it is no longer now.the last past of the ride is mostly down hill!!

KM 58
mt 851 variazione di altitudine

DAY 8: Arrivederci!

After breakfast at 9 am, is possible, on request, have one group shuttle to Siena train station from where you can connect to Florence and Rome.


  • Informative tour leaders throughout the program
  • Van support
  • Guide bike
  • Welcome & Last dinner

Accomodations & Meals

  • All accommodations
  • All breakfasts


  • Use of a carbon road bike or gravel bike
  • Shuttle at the beginning and end of your bicycle tour in Tuscany, as well as for certain specified activities mentioned in the program.
  • Lunch and dinner (excepet for the welcome and last dinner)
  • Wine and alcoholic beverages


  • Accommodation in a 17th-century mill, whose remains are still visible
  • A central position that lets you experience 7 spectacular Tuscany cycling routes in 7 different parts of Siena Province
  • Breakfasts inspired by the localism movement for sustainable food
  • Relax at the spa and thermal springs in Rapolano Terme we have discount for Therme.


PRICE: 1150 €
TERRAIN: Rolling with hills
MARCH 14/21-21/28
APRIL: 4/11 – 18/25 – 25/02 MAY JUNE: 20/27
JULY: 11/18 – 18/25 AUGOST: 22/29
OCTOBER: 10/17 – 17/24 – 24/31 NOVEMBRER: 7/14 – 14/21

Do you need a bike?
Bike rental service 280€ a week