Cycle the Wine Regions of Tuscany

Cycle the Wine Regions of Tuscany

Trip Highlights

  • Medieval villages & hilltop towns
  • Staying in a quintessential Tuscan Estate
  • Regional culinary specialities
  • Cypress lined hills & vineyards

Trip Summary

The Tuscan landscape of the Val d’Orcia will excite you with its natural beauty. You are in for a thrilling ride along steep valleys, dense forests, rivers and the legendary “badlands” eroded clay slopes. Mountain bike by picturesque farmhouses nestled amidst olive groves, vineyards and fig trees on your way to the hot spring hamlet of Bagno Vignoni and the heavenly Renaissance city of Pienza. You shall visit captivating palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red “Brunello”.


Moderate trip on hilly terrain, very little shade on roads (Daily climb 350 to 750m). The rides follow mostly well asphalted country lanes and smooth turf roads (approx. 35% of the time) with very little traffic. More traffic near larger towns.


Make your own way to Buonconvento. For your 4 nights, you will be staying at an organic farmhouse (agriturismo) nestled amidst the magnificent rolling countryside of the Crete hills south of Siena. This large Tuscan estate produces olive oil, organic cereals and pasta that are used to prepare the typical regional dishes you will enjoy at their restaurant.

Meals:  D

A great first ride through the countryside on well kept dirt roads to Murlo. 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. Return to Buonconvento.

Meals:  B,D

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.

Meals:  B,D

Climb uphill to the renowned monastery of Monte Oliveto Maggiore with its delightful frescos and botanical garden. After replenishing your soul, follow a winding route past isolated villages until you reach a row of hundreds of cypress trees, inviting you to visit the stunning Sant’Anna in Camprena monastery. Admire the frescos then finish your day in the lovely town of Pienza.

Meals:  B

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 thermal waters, enjoyed by the Romans and home to the legendary water nymphs. Ride back to Pienza along gently undulating hills through unspoiled countryside embracing the essence of Southern Tuscany.

Meals:  B

From Pienza, travel along immensely panoramic roads past the medieval stone-built hamlet of Monticchiello. Ride up a remarkable limestone ridge and enjoy breath-taking 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 before freewheeling back to Pienza.

Meals:  B

The ride today is mostly on gravel road, gentle rolling hills in the most beautiful countryside of the Orcia valley. Half way you can stop in Lucignano d'Asso, a tiny village on the L'eroica cycle route. Then you ride back to the organic farm of Pieve a Salti where you spend your last evening.

Meals:  B,D

After breakfast a short transfer takes you down to Buonconvento (arrange the time with the reception in advance), where you can catch the local bus or train to the airport for your onward journey.

Meals:  B

What's Included

  • 7 breakfasts, 4 dinners
  • 7 nights in 2-3 star hotels & agriturismo
  • Hybrid bike, pannier and odometer (1 per 2 bikes)
  • Vehicle transfer day 8
  • Luggage transfer (1 bag per person not weighing anymore than 20kg)
  • Information pack including route notes & maps
  • GPX tracks
  • Emergency hotline

What's Not Included

  • 2 evening meals, all lunches & beverages
  • Entrance fees
  • Travel insurance
  • Travel to the start and from the end point of the trip
  • Personal expenses such as laundry and phone calls
  • Tourist taxes €1.00 - €2.50 per night
  • E-Bike, rear bags & odometer €216.00 - must pre-book

Upcoming Travel Dates


Duration:8 Days
Starting Point:Buonconvento
Finishing Point:Buonconvento
Activities:self-guided cycling
Grade:moderate  Click for more information
Trip Code:JTS
Prices From:GBP£1150 Per Person
Single Supplement:GBP£200  Click for more information
Solo Traveller:GBP£290  Click for more information
Please do not book any flights or extra arrangements until such time that your booking is confirmed by Sherpa Expeditions by phone or email.