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  • self guided cycle
  • 4 nights 3 star agriturismo
  • 2 nights 2 star hotel
  • 7 Breakfasts

8 Days£1310GBP


Trip Code: JTS

Trip highlights

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

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”.



Starting Point:


Finishing Point:


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:  Nil

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

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

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

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


  • 7 breakfasts
  • 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)
  • Digital information pack: navigational App (can be used offline) with route notes & maps. Smartphone essential
  • Emergency hotline

  • 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
  • E-Bike, rear bags & odometer - must pre-book
  • A supplement will apply if you are travelling solo or book a single room
  • Guide - this is a self guided holiday

Bike information




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. *Please note that by Italian law, you can ride an electric bike if you’re 14 or over. For cyclists 14-18 years, wearing a helmet is compulsory.

Departure dates

Daily 26 Mar to 31 Oct


*Please note that by Italian law, you can ride an electric bike if you’re 14 or over. For cyclists 14-18 years, wearing a helmet is compulsory.

Priceper person from


Options & Supplements*
  • Electric Bike SupplementGBP£100
  • Single Room SupplementGBP£240
  • Solo Traveller SupplementGBP£400
*Prices listed are per person

Trip reviews

Why travel with us

Personal Experience

We've been walking and cycling the planet for over four decades and are passionate about delivering exceptional service. Combined, we’ve travelled to virtually every corner of Europe, and are eager to share the many benefits of travelling on foot or by bike.

Great Value & Quality

Our well priced trips offer great value for money. Included in your package are comprehensive route notes, maps & guide books along with bag transfers and locally run accommodation. We take the stress out of organising your holiday.

Self-Guided Specialists

We have been operating active self guided holidays since 1973. We handle all the necessary logistics so that you can relax and explore your destination at your own pace. Many of our tours depart daily, giving you even greater flexibility.