Montepulciano Val d'Orcia E-Bike Tour to Pienza and Monticchiello




The private e-bike tour starts from Montepulciano and develops a circular route towards Pienza and Monticchiello, crossing some of the most iconic landscapes of the Val d'Orcia. The route measures about 38 km with 684 m of positive elevation gain and altitudes between 321 and 546 m: intermediate level. The indicative duration is 4-5 hours, excluding stops. The itinerary alternates paved secondary roads, dirt roads, stretches of countryside, and panoramic ups and downs, with possible short sections open to traffic. During the tour, you cycle through hills, cypress trees, estates, and continuous views of the Tuscan countryside. Pienza, with its historic center recognized by UNESCO, represents one of the main stops, while Monticchiello retains a more intimate and medieval character, ideal for a break. The tour is scenic and not technical, but it features climbs to tackle at a regular pace. It is recommended especially in spring and autumn; in summer it is preferable to leave early in the morning.
Your experience
Stop 1
The temple was born in 1518 around a Marian fresco considered miraculous. Antonio da Sangallo the Elder designed it in Greek cross, condensing here the Renaissance ideal of the perfect central-plan building. The project provided for two towers: only one was completed.
Stop 2
In 1459 Pope Pius II entrusted Bernardo Rossellino with the transformation of his native village of Corsignano into an ideal city. In just three years, the heart of Pienza was born: a space designed like a perspective scene, where civil, religious, and family power dialogue according to Renaissance humanism.
Stop 3
This Romanesque church from the 12th century preserves an even older cylindrical tower and a small crypt. In its baptismal font received baptism Enea Silvio Piccolomini, future Pius II, and his nephew Pius III: a surprising link between the rural church and two popes.
Stop 4
The walls of Monticchiello were started in 1259 and the tower in 1260, when the village guarded the Sienese border. In 1944 about seventy partisans resisted much superior forces. Since 1967, Teatro Povero transforms inhabitants into authors and actors of their own collective memory.
What’s included
- Access to the self-guided tour via the Outdoora app, to be used on your smartphone.
- Phone carrier
- App access instructions provided after the reservation.
- Bicycle use
- Remote assistance for the rental point during the tour, if necessary.
- Step-by-step navigation, voice directions, stops and points of interest.
Not included
- Meals
- Additional services (insurance/damage, transfer, etc. if provided).
Meeting and pickup
Is it possible to park directly at the store. The area is rich in parking
Before you go
- Public transportation options are available nearby
- Not recommended for travelers with spinal injuries
- Not recommended for pregnant travelers
- Not recommended for travelers with poor cardiovascular health
- Travelers should have a high level of physical fitness
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
Check the policy for your selected date and option before booking.
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