Chianti and Val d'Orcia

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Bike Tours, E-bike tours, Gravel bike tour, MTB cycling holidays, Road cycling holidays


7 days





The beauty of this package is in the freedom it offers: without a guide, you are free to decide the timing, pace, and stops of your journey. Travel freely, travel your way!

3/5 Medium

Moderate, between 35 and 85 kilometers per day with an elevation gain between 300 and 1000 meters.



The starting point is different from the ending point, with overnight stays in different hotels and daily stages.


Day 1: San Quirico d’Orcia
Individual arrival, dinner and overnight stay at the Hotel, residence and SPA located in San Quirico d'Orcia, in the heart of Val d'Orcia. Upon your arrival, you will receive instructions on how to best tackle each stage.

Day 2: La Val d’Orcia (56 km; +/-910 m)
Enjoy the views of Val d'Orcia, one of the most suggestive places in all of Tuscany and a UNESCO World Heritage Site. Visit Pienza, the ideal Renaissance city, also famous for its pecorino cheese. Then pass through the streets and squares of Montepulciano and arrive at Monticchiello, a small medieval village of extraordinary charm. Free time before dinner to relax in the pool or at the SPA. Dinner and overnight stay in the hotel.

Day 3: Montalcino and Brunello (54 km; +/-1030 m)
Continue your journey to Bagno Vignoni, a charming medieval village where hot springs flow from a basin in the center of the square. Climb towards Castiglione d’Orcia and Rocca d’Orcia: the view will reward your effort! Cycle further to the Abbey of Sant'Antimo, one of the most beautiful Romanesque churches in Tuscany, and again uphill to Montalcino, a medieval town surrounded by precious vineyards and home to Brunello. Finally, a descent awaits you to Buonconvento, one of the most beautiful villages in Italy. Dinner and overnight stay at a typical Tuscan farmhouse equipped with SPA, riding stable and restaurant.

Day 4: The Crete Senesi and Siena (54 km; +/-890 m)
Today you will enjoy an unforgettable bike ride surrounded by the landscapes of the Crete Senesi until reaching Siena. Cross the Crete Senesi, where Badlands and clay lands alternate in this suggestive territory. Reach the Abbey of Monte Oliveto Maggiore, with its stunning cycle of Renaissance frescoes. Also allow a brief stop in Asciano, center of the Crete Senesi, rich in churches and museums. Siena appears on the horizon and staying in this city will make your bike trip unique. Free dinner and overnight stay in a hotel located in the center of Siena.

Day 5: The Chianti (52 km; +/-980 m)
Proceed towards Castelnuovo Berardenga and the landscape museum and push yourself to the villages of Villa A Sesta and San Gusmè, small jewels of the Chianti region. Visit the Brolio Castle, symbol of Chianti and taste its excellent wines. Venture into the streets of Gaiole, surrounded by greenery, which is the town where L'Eroica was born in 1997. Then reach Radda in Chianti, where the alleys and walls offer an unmissable view of the vineyards. Dinner and overnight stay at a hotel located in Radda in Chianti.

Day 6: Panzano and Greve in Chianti (55 km; +/-800 m)
Today you will ride in the Florentine Chianti. On your way you will come across Panzano, a picturesque village located on the hills of the Chianti. Here we recommend that you stop at the famous butcher shop of Dario Cecchini and savor some of his excellent cold cuts and cheeses. Heading towards Greve in Chianti, you will cross the Florentine Chianti, a wine region famous for its precious wines where, if you wish, you can stop for a tasting. Continuing the itinerary you will then arrive in Greve in Chianti, a charming medieval town located in the heart of Chianti. Admire the famous triangular square, which hosts the market on Saturday mornings where you can buy fresh local products. You will leave Greve in Chianti to head towards Piazzale Michelangelo in Florence, located on the hill in front of the city's historic center. This square offers a spectacular view of the city, the Arno River and its surroundings. We also recommend you visit the nearby Rose Garden.

Day 7: Florence
After breakfast, end of services and individual departure.

By choosing to travel by bike with us, you help us make the world a better place: we plant a tree for every trip sold

Why book online on Cyclando?

Because we guarantee you the lowest price and if your tour is not available or confirmed, you can always opt for the refund of the amount paid, or choose another tripfrom the over 800 on the platform.

Our cancellation insurance is the most advantageous you will find around!


Cancel for any reason

Trip cancellation for any documentable reason: pregnancy, illness, work and more, guaranteed.


Coverage of all costs

Full insurance covers all travel costs and penalties from companies, without worries.


Refund in 7 days

With Smart Claims, we guarantee fast refunds in just 7 days for complete peace of mind.

✅ What is included in the trip?

  • Travel/Medical Insurance 24/24
  • Overnight stay and breakfast
  • Luggage transfer
  • Local telephone assistance 7/7
  • Detailed description and maps of the itinerary
  • GPS or navigation APP
  • 2 dinners (drinks not included)

❌ What is not included?

  • Transfers not listed as "Included"
  • City tax
  • Tips
  • Journey to/from the starting point of the tour
  • Meals and drinks not listed as "Included"
  • Bike rental
  • Extras
  • Entrance fees, ferries and anything not listed as "Included"
  • Welcome briefing
  • Bike return to the starting point

💸 Cancellation fees

  • Time Range
  • Full refund
  • More 31 days of departure
  • 75%
  • From 30 to 31 days before departure
  • 50%
  • Up to 7 days before departure
  • Not refundable

Chianti and Val d'Orcia

  • To live an authentic adventure riding a bike surrounded by the magnificent Tuscan landscapes
  • To visit the small but fascinating Pienza, an ideal city of the Renaissance
  • To take the characteristic streets of the beautiful villages of Montepulciano and Montalcino
  • To cycle surrounded by the magnificent views in Chianti Fiorentino
  • To cross iconic places like the Val d'Orcia, Pienza, Montalcino and the biking in Chianti

🙋 Frequently asked questions

  • Can I bring my own bike?

  • What kind of assistance will I have during the trip?

  • How do I know if a tour is within my capabilities?

  • What is the cost of renting bicycles?

  • Are rented bikes equipped with accessories like lights or bags?


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Starting from 1094per person

stariicon4.9/5on15 reviews

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Minimum participant number = 2




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