8-day Val d'Orcia Cycling Holiday

Upon arrival in the charming medieval town of Buonconvento, rich in history and architecture with 700-year old walls, a transfer will take you to the agriturismo (farm house) where you will stay for the next four nights. If you have rented bikes with us, they will be waiting for you at the accommodation.

Ride through the bountiful, uncontaminated countryside to Murlo and immerse yourself in the dense woods as you ride by the Crevole River. Continue past steep cliffs to the sweet smell of bright yellow flowers and through an enchanting oak tree forest to La Befa. A short part of the trail is too narrow or rocky to cycle (about 300m) however the exhilarating views are more than worth the effort.

Challenge: 3.5 hours, 33 km / 20,5 mi, 584m ascent, 675m descent

Pedal through vibrant fields of sunflowers past Buonconvento to the heart of the Brunello wine district. The Monte Amiata volcano lures above as the surrounding countryside transforms into endless olive groves and vineyards. Ride steeply up to the fortified city of Montalcino where you can visit its magnificent 14th century fortress and Palazzo Comunale, then return to Buonconvento along remote back roads.

Challenge: 6 / 3 hours, 42.5 - 24 km / 26,5 - 15 mi, 1177 / 587m ascent, 1177 / 587m descent, optional extention to Montalcino 6 km

Climb uphill to the renowned Monastery of Monte Oliveto Maggiore with its delightful frescoes and botanical garden. After replenishing your soul, follow a winding route past isolated villages to until you reach a row of hundreds of cypress trees, inviting you to visit the stunning Santa Anna in Camprena monastery where "The English Patient" was filmed. Admire the frescos then finish your day in the lovely town of Pienza, another UNESCO heritage site

Challenge: 4.5 hours, 37.7 km / 23,5 mi, 1000m ascent, 756m descent

Today is a relaxing day in which you will travel on smooth country roads to the medieval hamlet of Bagno Vignoni where you can rest and swim in its healing hot thermal waters, enjoyed by the Anceint Romans and home to the legendary water nymphs. Ride back to Pienza along gently undulating hills through unspoiled countryside and embrace the essence of Southern Tuscany.

Challenge: 3 hours, 27.7 km / 17 mi, 674m ascent, 674m descent

From Pienza, travel along an immensely panoramic road past the medieval stone-built hamlet of Monticchiello. Ride up a remarkable limestone ridge and enjoy breathtaking views of the Val d'Orcia. Gather your strength as you make the climb up to Montepulciano. Upon arrival, celebrate with a glass of the famous local Vino Nobile wine. Head back down happy and giddy towards Pienza !

Challenge: 4.5 hours, 34 km / 21 mi, 1000m ascent, 1000m descent

Day 7 offers you a brilliant medieval experience. Follow an ancient pilgrimage route to the fortified town of San Quirico d'Orcia. Promenade its narrow streets full of well-preserved history and visit a 16th century Italian garden. After a ride across an arched medieval bridge and past the Tuoma stream, the road climbs and opens, revealing enchanting 360° views of Southern Tuscany's majestic landscape.

Challenge: 2.5 hours, 24 km / 15 mi, 400m ascent, 654m descent

 After breakfast a short transfer takes you down to Buonconvento where you can catch the local bus or train to the airport, unless you have booked a transfer or extra services with us.

Villages along the way: Buonconvento