Land of Siena

Name: Land of Siena
Brand: Cyclando
Price: 810 EUR
Availability: InStock

Chianti

Look at the map

See all the photos

Look at the map

Tour

Bike Tours, E-bike tours

Duration

8 days

Distance

315Km

Self-guided

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.

Ring

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

Description

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 45 to 44 days before departure
65%
From 44 to 27 days before departure
50%
From 27 to 10 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

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?
Of course! You can participate in any tour with your own bicycle or rent one. However, we recommend renting because not all spare parts are the same, and only with our bikes can we guarantee the best mechanical assistance.
What kind of assistance will I have during the trip?
You will always have an emergency phone number to refer to. In self-guided trips, you should be able to perform minor repairs, like replacing a tube in case of a puncture, or fixing a dropped chain, but you can always count on local assistance for more serious breakdowns.
How do I know if a tour is within my capabilities?
We classify tours on a scale from 1 to 5 based on length, elevation, and complexity of the itinerary, but if you have doubts, contact us and we will help you find the most suitable journey for you.
What is the cost of renting bicycles?
The rental cost varies depending on the bicycle model and the duration of the tour. For some tours, we offer the possibility to rent different types of bicycles. During the purchase process for each route, you will be asked to indicate your preferred bike type and the corresponding price will be shown, so you can choose freely and without surprises.
Are rented bikes equipped with accessories like lights or bags?
Yes, rented bicycles are equipped with all necessary accessories to comply with road traffic regulations (lights, bell, etc.). A lock, repair kit, and a bag to carry everything you need for a day in the saddle are always included in the rental. Additionally, we offer the option to request extra accessories based on your needs.