8 days

Cycling on peaceful country roads through an idyllic landscape of lush green fields and cypress-lined hills

Stay in a quintessential Tuscan Estate with onsite wellness resort and organic food produced on-site

Discover the natural, artistic and cultural treasures of the Val d’Orcia, on the UNESCO world-heritage list

 Explore incredibly well-preserved medieval and renaissance villages and hilltop towns

Enjoy the warmth of the friendly Tuscans and the delicious regional culinary specialties

Cycling in the Val d’Orcia: self-guided cycling holiday

Cycle among undulating green hills in the World Heritage Tuscan landscape of the Val d’Orcia on this self-guided cycling holiday. This is the Tuscany of your dreams, where time seems to have stood still. Glance at the picturesque farmhouses nestled amidst the olive groves and vineyards. Pass walnut and fig trees on your way to the thermal baths of Bagno Vignoni, and then explore the labyrinthine streets and artisan workshops of Montepulciano. Discover Renaissance palaces, Romanesque churches, thermal baths, and prestigious wineries. Enjoy a glass or two of the divine local red “Brunello” as you soak up the panoramic views from charming hilltop towns.


This is a moderately difficult cycling trip on hilly terrain (Daily climb 350 to 750m). With a reasonable level of fitness, it is not overly demanding. The routes follow mostly well asphalted country lanes and smooth turf roads (approx. 35%). There is generally very little traffic, with more near the larger towns. There is very little shade on the roads, so sun protection is important.

Four of the daily itineraries follow circular tours, so you can easily include a rest day if you wish. It is also possible to lengthen or shorten the routes on several days. E-bikes are also available for this trip if you want to make the cycling a little bit easier!

8 DAYS/7 NIGHTS From €880 per person sharing*

*Discounts available for groups of 3 in triple room. Please enquire for prices.
*A single supplement charge will apply for solo cyclists.

BIKE RENTAL If you don’t bring your own, you can rent a bicycle from us. You will find it waiting for you in the Hotel’s storage room, fitted to your requirements. Our adult hybrid-bikes are provided with comfortable seats, reliable components, 21 gears and Shimano Alivio components. All bikes are cleaned and overhauled before delivery.

All bikes are equipped with a padlock and key that must be used at all times when not riding the bike, as well as rear pannier bags, phone holder, front and back lights, puncture repair kit, pump and spare inner tube, all of which you should know how to use. One of every 2 bikes has a KM distance counter.


  • Hybrid/Trekking bike (21-gear): €175
  • E-bike: €260

Prices include bike delivery, collection and theft insurance.

ACCOMMODATION The accommodation in Buonconvento is a true 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 can enjoy at their restaurant.

The accommodation is 3-star equivalent, decorated in rustic Tuscan style, the rooms are simply and snug, with private bathrooms, telephone, hair dryer, central heating, TV and Air Condition.  The large outdoor pool near the restaurant is open from June to September, the rest of the year you can enjoy the indoor heated pool and the wellness centre where they also have a Turkish bath sauna, massage and manicure and pedicure.

The accommodation in Pienza is a small comfortable family-run 3* hotel, located 100 metres from the city gates of the historic village of Pienza. The hotel is in a quiet area, with a nice garden, swimming pool and private car park. All the bedrooms have private bathrooms, mini bar, satellite TV, AC and telephone. When the weather is nice, you can enjoy breakfast out on the terrace overlooking the garden. In Pienza it is possible to upgrade to 4* hotel depending on availability. Extended continental buffet breakfast is included each day of the tour and a 3-course dinner (drinks excluded) every night at the accommodation in Buonconvento. Dinner is not included in Pienza.

You can find below the standard hotels of this trip. If a hotel is fully booked, then we will book a similar one for you and inform you about the alternative booked.

AVAILABILITY You can start on any day of the week, subject to availability, between March 23rd and October 31st.
7 x overnight stays in selected agriturismo and hotel
7 x breakfasts
Luggage transport on day 4 and day 7
Day 1: transfer from Buonconvento train station to Pieve a Salti
Day 8: transfer from Pieve a Salti to Buonconvento train station
Detailed route notes and maps with tracks on
GPS tracks
Navigation App
24/7 telephone support
Flights & travel insurance
Lunches or dinners not specifically mentioned
Travel to/from Buonconvento at start/end of trip
Anything else not mentioned in the Included section
Bike rental
Additional nights before, during or after trip
Single room supplement

Day 1: Arrive in Buonconvento

The starting point for your trip is the charming medieval town of Buonconvento, rich in history and architecture with 700-year old town walls. A transfer is arranged to take you to the agriturismo (farmhouse) 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.

Overnight: Buonconvento


Day 2: Circular cycling route via Murlo and La Befa

Distance: 33 km | Ascent: 584 m | Descent: 675 m | Time: 3½ hrs approx.

Ride through the bountiful, unspoiled countryside to Murlo and enjoy the tranquillity of dense woodlands as you cycle along the Crevole River. Continue past steep cliffs with 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.

Overnight: Buonconvento


Day 3: Cycling through the Brunello vineyards of Montalcino

SHORT LOOP: 24 km | Ascent: 587 m | Descent: 587 m | Time: 3 hrs approx.


LONG LOOP: 43 km | Ascent: 1177 m | Descent: 1177 m | Time: 6 hrs approx.

Optional extension to Montalcino: 6 km

You have the option of a shorter or longer cycling route today. Both routes take you through vibrant fields of sunflowers past Buonconvento to the heart of the Brunello wine district. The Monte Amiata volcano forms an imposing backdrop as the surrounding countryside transforms into endless olive groves and vineyards. A steep climb takes you 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.

Overnight: Buonconvento


Day 4: Cycle from Buonconvento to Pienza

Distance: 38 km | Ascent: 1000 m | Descent: 756 m | Time: 4½ hrs approx.

The early part of today’s route features a climb to the renowned Monastery of Monte Oliveto Maggiore. It is well worth a stop to enjoy its delightful frescoes and botanical garden. After replenishing your soul, follow a winding route past isolated villages until you reach a row of hundreds of cypress trees. These mark the entrance to the stunning monastery of Santa Anna in Camprena, made famous by the movie “The English Patient”. Admire the frescos then finish your day in the lovely town of Pienza, another UNESCO heritage site

Overnight: Pienza


Day 5: Pienza to Bagno Vignoni circular cycle route

Distance: 28 km | Ascent: 674 m | Descent: 674 m | Time: 3 hrs approx.

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

Overnight: Pienza


Day 6: Pienza to Montepulciano circular cycle route

Distance: 34 km | Ascent: 1000 m | Descent: 1000 m | Time: 4½ hrs approx.

From Pienza, you cycle 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!

Overnight: Pienza


Day 7: Pienza to Buonconvento via Lucignano d’asso

Distance: 24 km | Ascent: 400 m | Descent: 654 m | Time: 2½ hrs approx.

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

Overnight: Buonconvento


Day 8: Arrivederci Val d'Orcia

Your cycling holiday in the Val d’Orcia comes to an end after breakfast this morning. A short taxi transfer is arranged to take you to Buonconvento train station, from where you can catch the local bus or train to the airport.

Arrival & departure info

  The most convenient airports to fly into are Florence (FLR), Pisa (PSA) and Bologna (BLQ).

All three airports can be easily reached with frequent and affordable public transport options.

  • From Florence airport (FLR), take the bus to Santa Maria Novella train station and then a train to Buonconvento (change in Siena).
  • From Pisa airport (PSA), take the train to Buonconvento (with 2/3 changes, depending on time. You always have to change at Pisa Centrale).
  • From Bologna (BLQ), take a bus to Bologna Centrale train station then a train to Buonconveto (change in Florence and in Siena).

Check train timetables on www.trenitalia.com.

Val d'Orcia cycling holiday
The historic walled town of Buonconvento in Tuscany's Val d'Orcia
Rolling hills of the Val d'Orcia
Cycling in the Val d'Orcia
Montalcino Fortress
The hilltop village of Pienza
Staircase in Pienza
Old well in Pienza
Signposts for the Capella di Vitalleta near Pienzad
Val d'Orcia landscape near Pienza
Typical cypress-lined avenue in the Val d'Orcia
Cappella di Vitaletta
Cycling in Val d'Orcia, Tuscany
Bagno Vignoni
Val d'Orcia cycling
Church of San Biagio, Montepulciano
San Quirico d'Orcia
San Quirico d'Orcia

Tour Reviews

There are no reviews yet.

Leave a Review