Land of Siena

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Bike Tours, E-bike tours


8 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!

4/5 Medium-Easy

Moderate-Difficult, between 50 and 100 kilometers per day with an elevation gain between 700 and 1300 meters.



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


Day 1: Siena
Individual arrival in Siena.

Day 2: Siena – Brolio – Castelnuovo Berardenga – Asciano  (49 km; +830 m)
Our Tuscany bike tour starts with a journey through the Chianti Senese and Crete, a 13 km dirt road in good condition. The main attractions of historical-artistic interest are the Brolio Castle, the village of Villa a Sesta and the inhabited center of Asciano. As for the natural aspect, you can admire the beautiful panorama of Chianti that, like magic, with its vineyards and forest, transforms into the raw landscape of the Crete.

Day 3: Asciano – Monte Oliveto – San Giovanni d’Asso – Pienza  (52 km; +800 m)
Today's stage is 12 km on a dirt road, the rest on asphalt roads with non-existent traffic, between the Crete Senesi and the Val d’Orcia. The main places of historical-artistic interest are the monastic complex of Monte Oliveto, the medieval village of San Giovanni d’Asso, the Monastery of S. Anna in Camprena, and Pienza, a jewel of a city from the Renaissance. As for the natural aspect, you can see another change in the territory, as we overlook the Val d'Orcia.

Day 4: Pienza – S.Quirico – Montalcino – Buonconvento – Murlo  (56 km; +750 m)
Today's stage of the Tuscany bike tour, takes place for 5 km on a dirt road and the rest on an asphalt route. The main places of historical-artistic interest are the historic centre of S.Quirico, the city of Montalcino and the small medieval village of Murlo. As for the natural aspect, you can admire the wide views of the wheat fields and the cypress groves, in addition to passing through the Val d’Arbia area.

Day 5: Murlo – Radi – Sovicille – Monteriggioni – Colle Val d’Elsa  (64 km; +680 m)
Today you will cycle towards the Montagnola and Val d'Elsa, following the traces of the ancient Via Francigena. Immersed in a context where history and nature intertwine, you head towards places steeped in historical and artistic charm. The walls of Monteriggioni rise before you as a silent witness to the past, a medieval jewel that tells stories and secrets of a distant era. Continuing the journey, you will find yourself in the vibrant heart of Colle Val d'Elsa, where the narrow streets of the old town echo with art and tradition. 

Day 6: Colle Val d’Elsa – Casole d’Elsa – Ulignano – Volterra  (47 km; +1110 m)
Today's stage leads you on asphalt roads to a stimulating climb towards Volterra. The itinerary will first take you to the historic center of Casole d’Elsa, with its picturesque alleys, and then to the imposing Volterra, cradle of centuries of history. In addition to cultural richness, the journey will offer breathtaking views to admire along the entire route: from the valleys of the Val di Cecina to the expanses of the Val d’Elsa. These views, where nature expresses all its majestic beauty, will make every pedal stroke a unique and unforgettable experience, a perfect balance between man's wonders and those of nature.

Day 7: Volterra – Il Castagno – San Gimignano – Certaldo – Siena  (47 km ; +600 m)
After leaving Volterra, you will find yourself on a completely asphalted route that will lead you to Certaldo. From here, the return to Siena will be by train. During the journey, you will have the opportunity to explore places of great historical and artistic value, such as the city of San Gimignano, famous for its imposing medieval towers that rise majestically towards the sky, and the picturesque historic center of Certaldo, rich in charm and history. The journey will also reserve natural surprises: a charming view of the Val d’Era hills, a true natural painting that expresses tranquility and beauty, awaits you to enchant you and complete this unique experience in the heart of Tuscany.

Day 8: Siena
After breakfast, the 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

❌ 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

💸 Cancellation fees

  • Time Range
  • Full refund
  • More 45 days of departure
  • 85%
  • From 44 to 45 days before departure
  • 65%
  • From 27 to 44 days before departure
  • 50%
  • From 10 to 27 days before departure
  • 20%
  • Up to 7 days before departure
  • Not refundable

Land of Siena

  • To try the exquisite rustic dishes of Tuscan cuisine
  • To dive into the Middle Ages in San Gimignano with its typical tower-houses and Ghirlandaio's frescoes in the Chapel of Santa Fina
  • To visit the Etruscan Volterra, on a hill in the middle of an unforgettable landscape, known for its alabaster and in recent years the vampire city of the Twilight saga
  • To reach Siena, a treasure of art and culture with the extraordinary Piazza del Campo, the Cathedral and the ancient streets lined with magnificent noble palaces
  • To discover Tuscany by bike, pedaling along the gentle hills and vineyards, passing through the Val d'Elsa, the Chianti, the Val d'Arno, the Val d'Orcia and the Crete Senesi

🙋 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


Due Ruote nel Vento srl

Best Price Guaranteed!

Starting from 810per person

stariicon4.9/5on15 reviews

How many of you will there be?


Minimum participant number = 2




Single room surcharge




Do you want to rent bikes?

Do you have any doubts of any kind?

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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