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Highlights
Visit picturesque Tuscan villages on bike tour of Val d’Orcia
Cycle through the Val d’Orcia, one of the most beautiful natural areas in Tuscany.
Stay in an authentic Tuscan estate with an onsite spa and an excellent restaurant.
Cycle to ancient medieval towns and through quintessential Tuscan countryside.
Dine on locally produced, organic Tuscan delicacies from nearby farmers.
This self-guided cycling tour through Tuscany takes you through the Val d’Orcia. This bike tour is an incredible opportunity to see one of Tuscany’s most pristine natural areas by bicycle. Cycling through quaint Tuscan towns, eating delicious, authentic cuisine, and relaxing in expansive accommodations await you on this lovely Tuscan cycling tour.
This cycling tour of the Tuscan countryside begins in Buonconvento, a medieval town with rich history. You can spend some time exploring the ancient architecture before retiring to your accommodations. You’ll be staying in a farmhouse inn, or “agriturismo”, with wonderful amenities. Take a dip in the pool before diving into the first of your authentic Tuscan dinners.
The next day, you’ll start your cycling tour of Tuscany’s Val d’Orcia region by riding through the pristine countryside to Murlo. Dipping down into the dense woods by the Crevole River provides another great view before riding through an oak tree forest filled with yellow flowers. The scenery is so divine, you might want to pause for a moment before arriving in La Befa.
The next leg of the Tuscany cycling through the Val d’Orcia Tour has you cycle through Brunello wine country. Pedaling through fields of sunflowers is sublime, and the view once you arrive at the Monte Amiata volcano is imposing. Continuing through olive groves and vineyards is blissful before you make it to Montalcino. This 14th-century fortress city is the perfect break for a snack and sightseeing before hopping back in the saddle to return to Buonconvento.
The next portion of your cycling tour of the Val d’Orcia involves an uphill ascent to the Monastery of Monte Oliveto Maggiore, a stunning sight with a lovely botanical garden. Then, a swim in the thermal pools near Bagno Vignoni is welcome on your legs. Cycling to Pienza on gently rolling hills is truly what Tuscany is all about, and you’re sure to be raving about the views all the way to Buonconvento and then on the trip home. Arrivederci, Val d’Orcia!
This self-guided cycling tour through Tuscany takes you through the Val d’Orcia. This bike tour is an incredible opportunity to see one of Tuscany’s most pristine natural areas by bicycle. Cycling through quaint Tuscan towns, eating delicious, authentic cuisine, and relaxing in expansive accommodations await you on this lovely Tuscan cycling tour.
This cycling tour of the Tuscan countryside begins in Buonconvento, a medieval town with rich history. You can spend some time exploring the ancient architecture before retiring to your accommodations. You’ll be staying in a farmhouse inn, or “agriturismo”, with wonderful amenities. Take a dip in the pool before diving into the first of your authentic Tuscan dinners.
The next day, you’ll start your cycling tour of Tuscany’s Val d’Orcia region by riding through the pristine countryside to Murlo. Dipping down into the dense woods by the Crevole River provides another great view before riding through an oak tree forest filled with yellow flowers. The scenery is so divine, you might want to pause for a moment before arriving in La Befa.
The next leg of the Tuscany cycling through the Val d’Orcia Tour has you cycle through Brunello wine country. Pedaling through fields of sunflowers is sublime, and the view once you arrive at the Monte Amiata volcano is imposing. Continuing through olive groves and vineyards is blissful before you make it to Montalcino. This 14th-century fortress city is the perfect break for a snack and sightseeing before hopping back in the saddle to return to Buonconvento.
The next portion of your cycling tour of the Val d’Orcia involves an uphill ascent to the Monastery of Monte Oliveto Maggiore, a stunning sight with a lovely botanical garden. Then, a swim in the thermal pools near Bagno Vignoni is welcome on your legs. Cycling to Pienza on gently rolling hills is truly what Tuscany is all about, and you’re sure to be raving about the views all the way to Buonconvento and then on the trip home. Arrivederci, Val d’Orcia!
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Tuscany Cycling through the Val d’Orcia Tour Itinerary
Day 1 Arrival in Buonconvento
Your cycling tour of Tuscany’s Val d’Orcia region begins in Buonconvento, a town rich in culture and history. Explore the medieval buildings before settling into the B&B where you’ll be staying.
Overnight Location: Hotel in Buonconvento
Distance: None
Meals: None
Day 2 Tour of Murlo and La Befa
The first full day of your Tuscan cycling tour starts off in one of the most beautiful parts of Italy, and the ride to Murlo is simply incredible. After cycling through the rolling hills of the Tuscan countryside, you’ll dive into the woods to ride alongside the Crevole River. Ascending towards cliffs brings you through a magical oak forest dotted with yellow flowers to the town of La Befa. Your effort will be rewarded with picturesque views.
Overnight Location: Hotel in Buonconvento
Distance: 3.5 hours, 33km, 584m elevation gain
Meals: Breakfast=
Day 3 Montalcino and Brunello Wine loop
Today’s ride captures some of the most beautiful scenery you’ll see on your Val d’Orcia cycling tour. Start by riding through simply perfect sunflower fields to Brunello wine country. Soon, the Monte Amiata volcano looms ahead and rows of vineyards and olive groves line the trail. If you wish to enjoy a longer ride today, cycling to Montalcino gives you the chance to explore a 14th-century fortress town and its vibrant Palazzo Communale before heading back to Buonconvento for the night.
Overnight Location: Hotel in Buonconvento
Distance: 3 or 6 hours, 24 – 23 km, 587 – 1,177m elevation gain
Meals: Breakfast=
Day 4 Cycle to Pienza
Today’s leg of your cycling tour through Tuscany starts with an ascent to the incredible Monastery of Monte Oliveto Maggiore. Take some time to snap photos of the beautiful frescoes and the lush botanical garden before hopping back on the bike towards Pienza. This section of the ride is simply incredible, with hundreds of cypress trees and small hamlets whizzing by. Stop by the Sant’Anna in Camprena monastery, where “The English Patient” was filmed. Pienza is a UNESCO World Heritage Site, and you’ll love spending time exploring its streets.
Overnight Location: Hotel in Pienza
Distance: 4.5 hours, 37.7 km, 1,000 m elevation gain
Meals: Breakfast
Day 5 Bagno Vignoni loop
Today’s ride is nice and relaxing. You’ll cruise down smooth trails to the hamlet of Bagno Vignoni. Take some time to rest your legs in the thermal springs here- keep an eye out for the fabled water nymphs! Cycling back to Pienza is relaxed and calm in the fading daylight.
Overnight Location: Hotel in Pienza
Distance: 3 hours, 27.7 km, 674 m elevation gain
Meals: Breakfast
Day 6 Montepulciano loop
Another stunning moment in your Val d’Orcia cycling tour is riding the panoramic trail from Pienza to Montepulciano. Pass the ancient hamlet of Monticchiello as you ascend a limestone ridge that gives you a great birds-eye view of the Val d’Orcia. It’s a tough ascent up to Montepulciano, but the glass of well-loved local Vino Nobile wine helps ease the pain. Have two glasses, because the way home is all downhill!
Overnight Location: Hotel in Pienza
Distance: 4.5 hours, 24 km, 1,000 m elevation gain
Meals: Breakfast
Day 7 Cycle to Buonconvento
The last full day of your Tuscany Val d’Orcia cycling tour starts on a historical pilgrimage trail to San Quirico d’Orcia. The narrow streets take you right back to the 16th century, with carefully preserved buildings and frescoes. Hop back on the bike for a ride across the Tuoma stream bridge, and then cycle into panoramic views of Tuscany’s gorgeous countryside.
Overnight Location: Hotel in Buonconvento
Distance: 2.5 hours, 24 km, 400 m elevation gain
Meals: Breakfast=
Day 8 Farewell, Val d’Orcia
Enjoy a final breakfast before a quick transfer starts your journey home. Rest those legs and revel in your memories of the wonderful trip.
Overnight Location: None
Distance: None
Meals: Breakfast
2026 Pricing for Tuscany Cycling through the Val d’Orcia
The departures are available from April 1 to October 31, 2026.
Accommodation on the Tuscany Cycling through Val d’Orcia Tour
This tour is based in 2-2.5 star hotels and farmhouse bed and breakfasts. The hotels offer ensuite rooms with rustic decoration. In some cases, accommodation listed below may need to be substituted for other, comparable accommodations.
Single Rooms and Solo Travelers
Solo travellers must pay a supplement (please check Dates and Prices for more info). However, it’s definitely possible to match single travellers up.
What’s included in the Tuscany Cycling through the Val d’Orcia Tour?
Meals
7 breakfasts are included.
Accommodations
Accommodation for 7 nights is included.
Transportation during the Tour
This tour includes transfers to and from Buonconvento on the first and last days of the tour, as well as rental bike delivery and pick up. This tour also includes two luggage transfers (on day 4 and day 7).
Also Included
- Route guides and notes
- Maps and detailed information packs
- 24/7 telephone guidance and support
- Bike theft insurance
Not included
- Bike rental
- Travel insurance
- Tourist taxes (€1 EUR per person daily)
- Personal equipment
- Anything not mentioned as ‘included’
Optional Extras
- Bike and biking equipment rental
- Any additional nights before or after tour
- Airport transfers
- How hard is the Tuscany Cycling through the Val d’Orcia Tour?
- Do I need a Visa to travel to Italy?
- Are meals included on the Tuscany Cycling through the Val d’Orcia Tour?
- Do I need insurance?
- How do I get to Buonconvento to start this tour?
- Is the Tuscany Cycling through the Val d’Orcia Tour guided?
- I’ve never been on a self-guided trip! How does it work?
- Where does the Tuscany Cycling through the Val d’Orcia Tour end?
- Can I rent a bike?
- Do I need special vaccines to travel to Italy?
- Are there any travel restrictions for Italy?
We rate this tour as a 3 / 5. While the distances aren’t great, the route is hilly and there is significant elevation gain. You can rent an e-bike if you’re looking for a bit of help on this tour.
Check with your local country about visa requirements. You could also try this website, though you should verify with your government.
7 breakfasts are included.
Yes. You will need to acquire travel insurance that covers hiking/walking. Get your Travel Insurance.
The best airport to arrive at is Florence (FLR). From FLR, take the bus to Santa Maria Novella train station and then transfer to a train for Buonconvento, which changes once in Siena. Check train schedules here.
No, you will be provided with maps, route guides, notes, and 24/7 telephone support to complete your self-guided tour.
Self-guided travelling is not difficult! For many, it is a preferred type of travel as you are in charge of your own time and pace. You are provided all the information on which direction you need to go daily. You don’t need to carry lots of things with you and can only carry your daypack, as your luggage will be picked up from your hotel daily in the morning and delivered to your destination hotel.
The tour ends in Buonconvento, where you can take the train to the airport.
Yes, you can rent an electric, hybrid, or mountain bike. Your rental includes a helmet, bags, odometer, padlock, repair kit, and water bottle.
Check with your family doctor.
Please check with your local government about travel restrictions before you book your tour. This map from the US Department of State provides an overview of the current status in countries around the globe. The UK‘s Foreign Office and Government of Canada also provide advice on foreign travel. Note that the travel advice may change depending on your nationality.
Customer Ratings
S-Cape Travel is a boutique tour operator focused on sharing the best walking, cycling, cultural and food & wine tours in Europe. Book one of their self-guided tours to live La Dolce Vita for a week or two, as you walk or cycle around Europe, enjoying incredible views and amazing food and wine.
