The villages of Chianti and Val d'Orcia

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Bike Tours, E-bike tours


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 the Val d’Orcia. On your arrival, you will be given detailed maps and guidance on how best to tackle each stage.

Day 2: The Val d’Orcia (56 km; +/-910 m)
Enjoy the landscapes of Val d’Orcia, one of the most evocative places in all of Tuscany and UNESCO World Heritage Site. Visit Pienza, the ideal city of the Renaissance, also famous for its pecorino. Then wander through the alleys 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 at the hotel.

Day 3: Montalcino and Brunello (52 km; +/-1030 m)
Continue your journey to Bagno Vignoni, a charming medieval village where thermal waters gush from the basin centered in the square. Climb towards Castiglione d’Orcia and Rocca d’Orcia: the view will reward the effort! Pedal further to the Abbey of Sant'Antimo, one of the most beautiful Romanesque churches in Tuscany, and again uphill towards Montalcino, a medieval town surrounded by prestigious vineyards and home to Brunello. Finally, descend to Buonconvento, one of the most beautiful villages in Italy. Dinner and overnight stay at a typical Tuscan farmhouse equipped with SPA, riding school, and restaurant.

Day 4: The Crete Senesi and Siena (54 km; +/-890 m)
Today you will take an unforgettable ride surrounded by the landscapes of the Crete Senesi to Siena. Cross the Crete Senesi, where Calanchi and Biancane alternate in this suggestive territory. Reach the Abbey of Monte Oliveto Maggiore, with its splendid cycle of Renaissance frescoes. Also allow yourselves a brief halt in Asciano, the center of the Crete Senesi, rich in churches and museums. Siena appears on the horizon and staying in this city will make your pedal journey unique. Free dinner and overnight stay at 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 fractions of Villa A Sesta and San Gusmè, small jewels of Chianti. Visit the Castle of Brolio, a symbol of Chianti, and taste the excellent wines. Head into the streets of Gaiole, surrounded by greenery, which is the town where L'Eroica was born in 1997. Afterwards, reach Radda in Chianti, whose alleys and walls offer an unmissable view over 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 pedal in the Florentine Chianti. On your way, you will encounter Panzano, a picturesque village located on the hills of Chianti. We recommend stopping at the famous butcher shop of Dario Cecchini and sampling some of his excellent cured meats and cheeses. Heading towards Greve in Chianti, you will cross the Florentine Chianti, a wine region famous for its fine 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 every Saturday morning where you can buy fresh local products. You will leave Greve in Chianti to head towards Piazzale Michelangelo in Florence, located on the hill opposite the historic city center. This square offers a spectacular view of the city, the Arno river, and its surroundings. We also recommend visiting 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
  • GPS or navigation APP
  • Luggage transfer
  • Local telephone assistance 7/7
  • Detailed description and maps of the itinerary
  • 3 dinners (drinks not included)
  • 1 technical assistance intervention along the route
  • Pickup of purchases made along the way

❌ 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 transfer back from arrival to 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

The villages of Chianti and Val d'Orcia

  • To explore the various and magnificent Tuscan scenery, such as the Val d'Orcia and the Crete Senesi
  • To visit the small but fascinating Pienza, the ideal city of the Renaissance
  • To take the characteristic streets of the beautiful villages of Montepulciano and Montalcino
  • To cycle surrounded by the beautiful panoramas in the Florentine Chianti
  • To experience an unforgettable holiday cycling through the beautiful landscapes of Tuscany
  • To cross Chianti by bike, among nature, history and tasting of fine wines

Package only on request.

Some of our tours are not available or bookable at the moment. If you are interested in this tour, then ask our team for more information on upcoming availability, or on a similar tour available or bookable immediately!

🙋 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?


Organized by



Cyclando srl

Tour operator with Europe Assistance RC Insurance 4249713 - Registered with the Guarantee Fund with A.I.A.V. Associazione Italiana Agenti di Viaggio trough IL SALVAGENTE s.c. a r.l.. All rights reserved.

VAT ID: 03880320365

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