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South Tuscany Cycle Tour

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Homepage > Italy > South Tuscany Cycle Tour
  • Duration: 4 or 7 Nights
  • Difficulty: Level 2-3
  • Tour Type: Self Guided
  • Availability: Daily from 23rd March to 31st October
  • Location: Buonconvento

South Tuscany

Tour Details

This cycling holiday in Italy is in the Val d’Orcia located just south of Siena. The Tuscan landscape of the Val d’Orcia will warm your heart like a classic photograph as you cycle the waves of undulating green hills, captured in time as if the Etruscans just rode through. On this bike vacation, make sure you glance at the 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 phenomenal labyrinth streets and artisan workshops of Montepulciano.

You shall visit Renaissance palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red “Brunello”. Soaring up high on invigorating hilltop towns, you’ll revel in delight. You will stay 4 nights in a Tuscan Estate with on-site wellness resort and organic food production. The restaurant serves entrees prepared primarily with their own local produce. Visit the natural, artistic and cultural treasures of the Val d’Orcia, on the UNESCO heritage list.

Starting Location


Price Includes

  • 4 or 7 Nights Bed and Breakfast
  • Accomodation with swimming pools
  • Navigation by Smart Phone App
  • Information Pack
  • Luggage transfers
  • Transfer on 4 night trip
  • Arrival and departure transfer from Buonconvento

Price Excludes

  • Transport before and after tour
  • Flights
  • Travel Insurance
  • Extra nights Florence , Siena or Pisa
  • Hybrid Rental Bike
  • E-Bike Rental Bike
  • City Tax
Trip Info


The Fattoria Pieve a Salti is a true organic agriturismo (farm) nestles amidst the magnificent rolling countryside of the Crete hills south of Siena. This large Tuscan estate-produced olive oil, organic cereals and much of the typical regional cuisine which you will enjoy at their restaurant. There are forty cosy room and apartments, some in the main farm while others are dotted around the vast estate. The bedrooms are simply and snug, furnished in the typical Tuscan farmhouse style and all rooms have private bathrooms, telephone, hairdryer and central heating – however, there is no TV or AC.

There is a large outdoor pool near the restaurant and heated indoor pool in the wellness centre where they also offer, for a fee, Turkish bath and sauna, massage and manicure and pedicure. Enjoy an idyllic calm. (Pool may not be open early season – May onwards)

Hotel Rutiliano

The Hotel Rutiliano is a small, comfortable hotel, 100 meters from the historic centre of Pienza. The hotel works as a bed and breakfast in a peaceful area, with a lovely garden, swimming pool and private car park. There are eleven double rooms with private bathrooms, mini bar, satellite TV, AC and telephone. The hotel also has a spacious reception area and breakfast room. When the weather is nice, you can enjoy breakfast out on the terrace overlooking the garden.

Route Characteristics

Cycling on hilly terrain, with sometimes very little shade on roads. The rides follow mostly well-asphalted country lanes and smooth turf roads with very little traffic. More traffic near larger towns.

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


4 night tour stays 4 nights in Fattoria Pieve a Salti, the tour includes Days 1,2,3, on day 4 you have a transfer to Pienza and you then have day 7 (becomes day 4) and 8 (becomes day 5).

Day 1Arrive 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 to the Agriturismo (farmhouse, Tuscan Estate) where you will stay for the next four nights. A delicious Tuscan dinner awaits you! If you have rented bikes with us, they will be waiting for you at the accommodation.

Day 2Buonconvento to Murlo and La Befa round tour. 20.5 miles 33km, up 584m

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.

Day 3 Buonconvento to Montalcino round tour 15-27 miles 24-43 km, up 587-1177m.

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. You can sample the world-famous Brunello wine and maybe arrange a crate to be delivered back home. Then you cycle back to Buonconvento along remote back roads.

Day 4Buonconvento to Pienza 23.5 miles 38km, up 1000m.

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 to 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.

Day 5Pienza to Bagno Vignoni round tour 18 miles 28 km, up 674m.

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 the unspoiled countryside and embrace the essence of Southern Tuscany.

Day 6 Pienza to Montepulciano round tour 20.6 miles 33 km, up 1000m.

From Pienza, travel along an immensely panoramic road past the medieval stone-built hamlet of Monticchielo. 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.

Day 7Pienza to Buonconvento via Lucignano d’asso 15 miles 24 km, up 400m.

Today your cycle tour is mostly on gravel road known locally at Bianca Strada or white roads. You shall experience gentle rolling hills in the most beautiful countryside of the Orcia valley. Around halfway on your bike tour, you can stop in Lucignano d’Asso, a tiny village on the L’eroica cycle route. This is a small hamlet which is extremely beautiful, when there you shall feel as though time has stood still, so beautifully restored by its current owner Countess Angelica Bandini Lucignanello. Yes, the hamlet is owned by a Countess! After your rest, you then ride back to the organic farm of Pieve a Salti.

Day 8Departure

After breakfast, a short transfer takes you down to Buonconvento where you can catch the local bus or train to the airport.


How to get there

By Plane
Fly to Pisa, Florence or Bologna airports and then by train to Buonconvento where we shall arrange your short transfer to the accommodation (5 minutes)

Book Now

2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
TUSSOUTH-4 (4 Nights)  from £570 Book Now
TUSSOUTH-7 (7 Nights)  from £893 Book Now
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South Tuscany