Siena Land in 5 days

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Bike Tours, E-bike tours


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


Day 1: Siena
Individual arrival in Siena and overnight stay.

Day 2: Siena - Brolio - Castelnuovo Berardenga - Asciano (49 km)
Our Tuscany bike tour begins with a up and down through the Chianti Senese and Crete, 13 km of well-preserved dirt road. 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 naturalistic aspect, you can admire the beautiful panorama of the Chianti that, as if by magic, with its vineyards and woods, turns into the most crude landscape of the Crete.

Day 3: Asciano - Monte Oliveto - San Giovanni d'Asso - Pienza (52 km) 
Today's stage takes place for 12 km on dirt road, the rest on asphalt roads with no 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 and the monastery of S. Anna a Camprena and Pienza, jewel city of the Renaissance. As far as the naturalistic aspect is concerned, you can see another change of the territory, as you gradually overlook the Val d'Orcia.

Day 4: Pienza - S.Quirico - Montalcino - Buonconvento - Murlo (56 km) 
The today's stage, of the Tuscany bike tour, takes place for 5 km on dirt road and the rest on asphalt track. The main places of historical-artistic interest are the historic center of S.Quirico, the city of Montalcino and the small medieval village of Murlo. As for the naturalistic aspect you can admire the wide panoramas on the wheat fields and the cypress groves, in addition to the passage in the area of the Val d'Arbia.

Day 5: Murlo - Siena (46 km)
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

❌ 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

Siena Land in 5 days

  • To visit the Brolio Castle and discover the beautiful historic center of Asciano, in the heart of the Crete Senesi
  • To breathe an atmosphere of other times in the monastery of Camprena and walk among the evocative monuments of Pienza, pearl of the Renaissance
  • To savor the true rustic Tuscan cuisine and the delicious wines of the area: the Brunello di Montalcino and the Chianti
  • To start and end in the beautiful Siena, which with its immense historical-artistic heritage, is among the most beautiful medieval cities in Italy
  • To live a memorable trip discovering Tuscany by bike, pedaling between Chianti, Val d'Orcia and Crete Senesi, between gentle hills and places of refined culture

🙋 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

Best Price Guaranteed!

Starting from 520per 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?


Chosen by 36 people

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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