Cycling Tuscany South of Siena (8d) - Italy
Short walks of generally 3-4 hours plus optional day excursions; level or slightly hilly terrain using well kept paths.
2. Average/ Moderate
Easy day walks with more strenuous excursions. 4-5 hours per day in hilly to mountainous areas using well kept, sometimes stony paths.
Strenuous day walks or trekking in mountainous areas. 5-7 hours per day, sometimes carrying backpacks with stuff for one night; altitude differences between 1,500-3,000 ft. (500-1,000 m.) per day.
Serious excursions in high mountains, sometimes carrying backpacks with stuff for several nights. 6-8 hours per day; altitude differences up to 3,600 ft. (1,200 m.) per day. Only for those with an excellent condition and without fear of heights.
Easy cycling in nearly flat areas; Little or no experience needed. Approx. 20-50 km daily. Bicycles with up to 3 gears will do.
2. Average / Moderate
Nearly flat to hilly areas with the occasional short climb. Approx. 30-65 km daily. Bicycles with minimum 7 gears will do.
Strenuous cycling with some steeper climbs. Some experience needed. Approx. 30-75 km daily. Bicycles with up to 21 gears needed.
Serious and strenuous in mountainous areas. Slopes are longer and/or steeper. Good physical condition needed. Experience and a mountain bike needed. Approx. 30-80 km daily.
You can choose from 4 different levels of comfort, although most of our trips are rated 2 or 3 (or a combination of the two) on our accommodation scale. We try to provide en-suite rooms where possible but on occasions this may not be possible on some tours.
We are constantly looking for hotels, B&B’s, guesthouses and mountain huts that offer a special location, ambience or atmosphere that fits the trip. Accessibility to the route and personal hospitality of the owners are part of our choice of accommodations.
A hotel, a pension or a mountain hut with all the basic facilities. Most rooms have a shared bathroom.
Fine hotels or B&B’s with basic to moderate facilities. Almost all rooms have a private bathroom.
A 3-star hotel, B&B or guesthouse. Comfortable rooms with private en-suite bathroom and often air conditioning. Some accommodations might have a swimming pool.
A 4-star chateau hotel or guesthouse. The rooms are relatively large with en-suite bathroom and air conditioning. A warm welcome and a high quality are guaranteed. Some hotels have a swimming pool or sauna.
Welcome to this individual cycling holiday in Tuscany. The landscape in Tuscany, near Val d'Orcia will warm your heart. During this cycling holiday you will ride along serene valleys, dense forests, rivers and the legendary “badlands” eroded clay slopes. Ride your bike along 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. During your cycle tour you will also visit historical palaces, Romanesque churches, thermal baths, and prestigious wineries serving the divine local red “Brunello”. Enjoy the famous hilltop towns, and a fine cappucino out on the terrace.
Tuscany Trip Highlights:
- Stay in a quintessential Tuscan Estate with onsite 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
- 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 specialties
- Total distance: 199 km, 124 mi.
The indicated routes on Google Maps are approximate.
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 to the agriturismo (farm house) where you will stay for the next four nights. A delicious Tuscan dinner awaits you! If you have rented bicycles through us, they will be waiting for you at the accommodation.
Day 2 Buonconvento to Murlo and La Befa round tour
Distance: 31 km, 19 mi, ↑550 m. Cycling on small paths through the bountiful and pristine 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 bike trip is too narrow or rocky to cycle (about 300 m) however the exhilarating views are more than worth the effort.
Day 3 Buonconvento to Montalcino round tour
Distance: 39 km, 24 mi, ↑600 m. Today is wonderful cycling 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 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.
Day 4 Buonconvento to Pienza
Distance: 38 km, 24 mi, ↑700 m. Ride your bike uphill to the renowned monastery of Monte Oliveto Maggiore with its delightful frescos and botanical garden. After replenishing your soul, follow a winding cycling 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. What a perfect day of cycling and exploration!
Day 5 Pienza to Bagno Vignoni round tour
Distance: 24 km, 15 mi, ↑300 m. Today is a relaxing cycling 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 and embrace the essence of Southern Tuscany.
Day 6 Pienza to Montepulciano round tour
Distance: 33 km, 21 mi, ↑750 m. From Pienza, cycle along an immensely panoramic road past the medieval stone-built hamlet of Monticchiello. Ride your bike 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 7 Pienza to Buonconvento via San Quirico d’Orcia
Distance: 34 km, 21 mi, ↑350 m. Day 7 offers you a brilliant medieval cycling experience. Cycle 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 bike 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 Arrivederci Val d’Orcia
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, unless you have booked a transfer or extra services with us.
- 7 nights accommodation with continental breakfast, all rooms with private bathrooms (for an image selection, please see Flickr)
- 4 dinners (in Buonconvento)
- Accommodations have a swimming pool
- Luggage transfer, normally provided by the accommodation itself (don't forget to label your belongings)
- 24-hour telephone assistance (simple puncture not covered)
- Detailed road book and maps are in English
- Flights and public transportation
- Travel insurance
- Bike rental
- City tax
- Admissions and entrance fees of any kind (when not previously agreed upon)
- Personal extras and expenses such as meals, drinks, phone calls, tips etc.
- Any items not mentioned in the program
Optional services (to be booked in advance):
- Additional night(s) at any of the accommodations (please use booking remarks field)
- Arrival and/or departure transfers to Buonconvento and back
- Single supplement surcharge $Cad 343.-
- Ask about our 3-person room rates
- 21 speed hybrid rental bike including 1 small front bag, 2 rear bags, 1 odometer every 2 bikes, helmet, water bottle, 1 repair kit and 1 padlock. Bike rental price $Cad 150.-
- Also Mountain bike available for same price
With a certain athletic attitude, the majority of the day are not really demanding. You’ll be in a position to fully enjoy the exhilarating sections through unspoilt country and nature areas. Four days you make circular tours, during these days you can eventually intercalate a resting day. Several days you can lengthen or shorten the rides. Moderate trip on hilly terrain, very little shade on roads (daily climb 350 to 750 m). The bike 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.
How to get there:
Best arrival and/or departure airports are Florence, Pisa or Bologna airport. The Florence airport has both major and low cost international flights. Several low cost carriers serve Pisa and Bologna.
From Florence airport take the bus to the Santa Maria Novella train station and then the train to Buonconvento, changing trains once in Siena. Travel time approximately 2.5 hours. From Pisa you take the train to Buonconvento, changing trains three times along the way: in Pisa Centrale, then Empoli and finally in Siena. Travel time approximately 3 hours. If you fly on to Bologna airport, you have to take the bus to Bologna Centrale train station, then the train to Buonconvento, changing trains twice – in Florence and in Siena. Travel time approximately 3.5 hours.
Tip: For online rail connections and reservations visit Rail Europe.