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Cycling in Tuscany: Val D'Orcia and Brunello Vineyards

Cycling in Tuscany: Val D’Orcia and Brunello Vineyards


Take an unforgettable dual-based cycling holiday through Brunello vineyards. The Tuscan landscape of Val d’Orcia will enchant you as you cycle the undulating green hills, passing by picturesque farmhouses nestled amidst the olive groves and vineyards. Pass walnut and fig trees on your way to the hot spring town of Bagno Vignoni, and then explore the labyrinth streets and artisan workshops of Montepulciano. You will visit Renaissance palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red Brunello.


  • Stay in a quintessential Tuscan Estate with an onsite wellness resort
  • Enjoy locally farmed organic food served in the Estate restaurant
  • Visit the natural, artistic and cultural treasures of the Val d’Orcia, on the UNESCO world heritage list
  • Wonderful landscapes, wide-open fields, cypress-lined hills and vineyards
  • Incredibly well preserved medieval and renaissance villages and hilltop towns
  • Peaceful country roads, friendly Tuscans and delicious regional culinary specialities

Click to view map


Day 1: Arrive in Buonconvento

Upon arrival in the charming medieval town of Buonconvento, rich in history and architecture with 700-year old walls, a transfer will take you from the train station to your agriturismo (farmhouse), where you will stay for the next three nights. If you have rented bikes from us, they will be waiting for you at the accommodation so you can give them a try before enjoying a delicious Tuscan dinner (not included).

Day 2: Murlo and La Befa Loop | 33 km

Ride through the bountiful 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 300 m); however, the exhilarating views are more than worth the effort.

Day 3: Brunello Wine District Loop | 24-42 km

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. There is a steep climb 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.

  • Cycling for the day (short loop): 24 km, ↑590 m590 m
  • Cycling for the day (long loop): 42 km, ↑1180 m1180 m
  • Accommodation: Agriturismo Pieve a Salti or similar

Day 4: Buonconvento to Pienza | 38 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 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 frescoes, then finish your day in the lovely town of Pienza, another UNESCO heritage site.

  • Cycling for the day: 38 km, ↑1000 m ↓760 m
  • Accommodation: Hotel Rutiliano or similar

Day 5: Bagno Vignoni Loop | 28 km

Today is a relaxing day on which you will pedal 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 Ancient Romans and home to the legendary nymphs. Ride back to Pienza along gently undulating hills through the unspoiled countryside and embrace the essence of Southern Tuscany.

  • Cycling for the day: 28 km, ↑675 m ↓675 m
  • Accommodation: Hotel Rutiliano or similar

Day 6: Montepulciano Loop | 34 km

From Pienza, pedal 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 do the climb up to Montepulciano. Upon arrival, celebrate with a glass of the famous local Vino Nobile wine.

  • Cycling for the day: 34 km, ↑1000 m ↓1000 m
  • Accommodation: Hotel Rutiliano or similar

Day 7: Pienza to Buonconvento via Lucignano d’Asso | 24 km

The day today 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. 

Day 8: Departure

After breakfast a private transfer will take you to Buonconvento train station.

What to Expect


Standard accommodation for this trip is in Agriturismo** and a charming 2-star countryside hotel, both with a swimming pool, in double/twin en-suite rooms. All places have been carefully hand-picked by us, and their quality is regularly monitored. We have tried to choose accommodations that offer friendly service, clean and comfortable rooms and local flavour.

Click to view default hotels

Pieve a Salti is located 5 km from Buonconvento, and it’s housed in a restored Tuscan farmhouse. Immersed in the Tuscan countryside, the farmhouse is set on two buildings located 1 km away from each other, offering rooms with a rustic style with wooden ceilings. It offers a TV, refrigerator, air conditioning, indoor and outdoor pools. Abundant buffet breakfast with local products.

Hotel Rutiliano is just 5 minutes walk from the historic centre of Pienza. Rooms are modern with a classic style and equipped with a TV, private bathroom, free Wi-Fi; there are a spa, a garden and a swimming pool. The breakfast buffet is good. The staff is friendly and welcoming.

*Hotels are subject to availability. In case a particular hotel is fully booked for your desired dates, we will replace it with a hotel of equal or higher value and quality level. We will provide exact accommodation details to you upon booking confirmation.

**What is an agriturismo? A combination of the words for “agriculture” and “tourism” in Italian — It is a farm-stay, but it’s also much, much more. Typically, an agriturismo is an independently-owned farm that the owners have decided to use partially for accommodation purposes, in a way similar to English or American bed and breakfasts. One of the best parts of staying in a traditional agriturismo? The food. An Italian agriturismo will usually serve guests food that was prepared from raw materials – vegetables, fruit, eggs, meat, and often wine and olive oil – produced on the farm or from other local merchants.


Breakfast is included each morning. When no restaurant is available on the route, lunches and snacks can either be bought from local shops, or packed lunch can be pre-ordered from your hotel the night before. You can have dinner at your hotel or nearby restaurants.

Difficulty & terrain

This is a fairly moderate trip on hilly terrain. The rides follow mostly well-asphalted country lanes and smooth turf roads (approx. 1/3 of the time) with very little traffic. You can expect more traffic near larger towns. Average daily distances vary between 30 km and 40 km, with daily elevation gain ranging from 350 m to 750 m. The trip is suitable for fit cyclists who have an active lifestyle (read more about difficulty grades). Once you arrive at your first hotel, you will receive a detailed information package, including a destination manual, route notes, and maps. Before the start date, you will also be sent GPS tracks, which you can load on any Garmin device or smartphone application that you are used to working with.

When to go

This trip is available from late-March until late-October, departing on any day of the week (subject to availability). The overall trip can be shortened upon request. Spring and autumn months are a preferred travel period if you want to avoid the summer heat of July and August. In September – October, you will enjoy pleasant temperatures and might also be able to catch the regional wine harvest.

Getting there

FCO up-to-date travel advice

Click to view travel options

By plane

Our recommended arrival/departure airports for this holiday are Florence (FLR)Pisa (PSA) and Bologna (BLQ), all served by major and low-cost international flight carriers.

By train or bus
  • 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.



  • 7 nights in hand-picked accommodations as listed in the itinerary
  • 7 breakfasts
  • Luggage transfer on Day 4 and Day 7 when changing hotels
  • Private transfer from Buonconvento train station to Pieve a Salti on Day 1
  • Private transfer from Pieve a Salti to Buonconvento train station on Day 8
  • A detailed information pack, route notes and maps with tracks on
  • 24/7 phone support by our local office/representative


  • Airfare and connecting land transfers
  • Lunches, dinners, drinks and snacks
  • Bike rental
  • Travel insurance (required – get a quote online)
  • Local tourist tax & entry fees (payable on the spot)
  • Personal expenses
  • Any items not specifically mentioned as ‘Included’ in the programme

Options, extras & supplements

  • Supplement applies to members of a group who require a single room / single use of a double room
  • This holiday is available for solo travellers; a supplement will be charged as accommodation and luggage transfer costs are not shared (we never mix and match – solo travellers will be accommodated in single rooms)
  • Bike rental, including Bike delivery to Pieve a Salti, theft insurance and collection from Pieve a Salti
  • Extra nights

Bike Rental

In case you would like to rent a bike from us, we can offer you a standard trekking bike, mountain bike or E-bike. All our bikes are equipped with phone holder, rear bags, odometer, repair kit, padlock, and helmet.

Sample models: Univega Terreno 5.0 Cross, Focus Whistler 27R 2.0, Univega Summit E LDT (Bosch)