Depart from the center of Siena and head out for the range -- that is, the hills of Tuscany. First hop in a comfortable minivan and go to the stables to meet your horse. After a brief safety talk, put on your riding hat and hop on the saddle. Do a quick practice riding session in a riding arena and when you're comfortable on your gentle horse, set off for the rustic Tuscan countryside.
Start out riding at a leisurely pace, following your guide, as you trot long secluded road and then into verdant forests. Follow trails that zigzag through the countryside and go through ancient rustic villages. Marvel at the countryside, which includes a patchwork of quilt-style landscapes, as well as villa-crowned hills and ancient villages made up of terra cotta-roofed house. Some of these trails are used as part of the Via Francigena, a centuries-old pilgrimage route that stretches from Canterbury in England all the way to Rome.
While the riding tour is more for novice or intermediate riders, more advanced riders will be given the chance to trot or canter through stretches of the countryside. After about 90 minutes on the trail, head back to the stables. Help groom and unsaddle your horse and then get in the minivan for the short drive back to your hotel in central Siena.