Castles, vineyards and amazing landscapes a few rides from Town

Starting from the Medici walls in Siena you can reach Chiantishire in a bike ride.

After admiring the ancient Basilica of Osservanza founded in 1490 by S. Bernardino of Siena and its clay artwork by Andrea Della Robbia, Sano di Pietro’s Madonnas and the wonderful view, the tour proceeds towards the Chianti hills, among rows of vines and fruit orchards.

Going past Villa Santa Regina, a location for religious retreats, Val di Pugna opens in front of you, dominated by ”Castello delle Quattro Torra” (Castle of the Four Towers) built in the XIII century, which is today a Bed & Breakfast, where it is still possible to visit the lovely gardens with its box hedges and bay leaf bushes, and surrounded by olive trees and cypresses.

Surprising views of stately homes and beutiful views of the countryside make you forget you are just 2 km away from the city.

So, pedalling along a cypress-lined avenue, you’ll get to Castel di Pugna in the site of the XII century manor. Today you’ll find a high-quality farm where you can stay for your holiday, taste local dishes in its restaurant and try the excellent Chianti Colli Senesi wine produced here. This is where some ancient native vines have been retrieved and planted again with love and professionality.

From the gardens in front of the Villa it is possible to admire a amazing skyline of Siena..


Half Day






from March to November

PRICE LIST (per person)

  • 2        people: € 120,00
  • 3        people: €   95,00
  • 4        people: €   85,00
  • 5/6     people: €   75,00
  • 7/8     people  €   70,00
  • 9/10   people: €   65,00

(tips not included)


  • E-bike hire, helmet, bags
  • Bike Guide

YOU CAN ADD (to pay in Winery)

  • Visit to the ancient dungeons and Cellars
  • Light lunch with tasting 3 kinds of wines which come with a tasting of the local cold cuts, pecorino cheese (fresh and mature), a bruschetta with homemade extra virgin olive oil.


Your name (required)

Your email (required)

Select a tour

Number of Persons

Tour Date

Custom requests

I have read and accept the Privacy-Policy

Note: Booking will be effective only AFTER You received our confirmation mail.