Day 1

Arrive at the ranch and settle into your accommodation. In the evening, enjoy your first dinner with your hosts and fellow riders. Your guide will outline the week’s riding program and answer any questions as you prepare for the adventure ahead.

Day 2

After breakfast, meet at the stables around 9:30 a.m. and set out on your first day in the saddle. The trail crosses the Pian del Lago plain—once a vast marsh known as Lake Verano, reclaimed in the 18th century under Grand Duke Pietro Leopoldo. Following the Via Francigena, you’ll pass Castello della Chiocciola, with its distinctive spiral tower, before reaching the medieval fortress of Monteriggioni, built between 1214 and 1219. After lunch, continue to Abbadia a Isola, once an “island abbey” surrounded by the old lake’s marshes, and then on to Castel Pietraio, your stop for the night.

Day 3

Set off from your overnight stop and ride towards the San Gimignano area, in the heart of the Val d’Elsa—a stunning region between Siena and Florence. Its roots trace back to the Etruscan era, but it was the Via Francigena that later transformed the Val d’Elsa into a thriving hub of culture and trade. You’ll follow peaceful country tracks and sections of the ancient pilgrimage route, stopping for lunch along the way— just as medieval travellers once did.

Day 4

Today’s route explores the Montagnola Senese, one of southern Tuscany’s most fascinating natural areas. This hilly region, with gentle elevations of 500–600 metres, has been inhabited since Etruscan and Roman times yet still retains much of its wild beauty. Along the way, you’ll pass the ruins of the Romanesque Nagli Chapel, the fortified village of Marmoraia with its ancient parish church, and the charming Borgo di Scorgiano, before returning to your accommodation.

Day 5

Today’s ride follows new trails through the Montagnola Senese as you make your way back towards the equestrian centre. For a time, you’ll leave the medieval atmosphere of the Via Francigena and step into more recent history, reaching Casa Giubileo on Montemaggio. This peaceful spot bears the memory of a tragic event from March 28, 1944, when it became the scene of one of the most moving episodes in Tuscany’s struggle for liberation during the Second World War. Here you’ll stop for lunch and, for those who wish, visit the Rooms of Memory before continuing your final ride back to the ranch.

Day 6

Today’s trail follows the Via Francigena toward the Hermitage of Lecceto, originally built between 1189 and 1223, later rebuilt in 1317 and expanded in 1344. Continuing on, you’ll visit the Hermitage of San Leonardo al Lago, home to a community of hermits recorded as early as 1112, and likely even older. Along the way, you’ll pass La Piramide, an obelisk commemorating the reclamation of Pian del Lago.After a lunch stop at the fortified village of La Villa, an official rest point on the ancient pilgrimage route, you’ll ride back to the equestrian centre, leaving the Castello della Chiocciola behind you. The adventure concludes in true Tuscan style—with an afternoon wine tasting.

Day 7

Enjoy a final breakfast at the ranch before saying goodbye to your hosts and fellow riders. Transfer to the airport for your onward journey, carrying with you lasting memories of your time riding through Tuscany and along the Via Francigena.