Italy's Tuscany Hilltop Villages Trail

Everyone knows that Tuscan cities such as Florence, Siena and Pisa, together with smaller towns like Lucca, Cortona and Arezzo, contain some of Italy's most famous artistic treasures. However, Tuscany is not just beautiful cities and villages and a wealth of art. Tuscany is also equally renowned for its glorious pastoral countryside and rich equestrian lifestyle. Here, a beautiful landscape combined with great food, excellent wine, and an appreciation of the outdoor life provides a truly memorable horseback riding vacation.

This ride takes you through one of the most horsy areas of Tuscany, the area around Siena. As if to prove its equestrian heritage, each year Siena hosts the Palio. The Palio features bareback horse races first recorded in 1283 but the race may have its origins in Roman military training. Thousands crowd into the piazza to watch the race, and rivalry between competitors is intense. The winner is rewarded with a silk banner.

Although our trail ride does not feature racing, it is equally impressive. You will be based at Il Poggio Equestrian Center not far from Siena. Each day you will venture out into the countryside in a different direction. Each night you will return to the comforts of Il Poggio, a true Tuscan dinner and your room with private bath.

The rides out take you over rolling hills, past vineyards and farms, through meadows, forests and small villages and across rivers. From Monte Cetona you can see the Tuscan countryside as you ride through the area abundant with chestnut trees and the world famous mushrooms. You will ride along the Via Cassia. This road was used by pilgrims on their way to Rome from France during the Middle Ages. You will also pass through one of the favorite ambush spots used by an Italian version of Robin Hood.

This horseback vacation also includes a day to explore Siena on foot. This is an opportunity to stretch legs and visit the many shops, restaurants and cafes of this beautiful medieval city. You may also want to visit Siena's Duomo, one of Italy's greatest cathedrals, which features sculptural masterpieces by Nicola Pisano, Donatello and Michelangelo.