Tuscany’s Via Francigena

7 Days | From £1694pp

Italy ( Best airport: Florence/Pisa)

Riding along the Via Francigena is like stepping back in time. From the saddle, you’ll trace the footsteps of ancient pilgrims, following winding trails through olive groves, vineyards, and medieval hilltop villages that seem untouched by the centuries. The pace of horseback travel brings you closer to the spirit of this historic route—unhurried, mindful, and deeply connected to the land.

Since the early Middle Ages, the Via Francigena has guided travellers from across Europe to Rome, crossing some of Tuscany’s most culturally and environmentally rich landscapes. Today, you’ll experience it as those early pilgrims once did—on horseback—accompanied by well-trained, responsive horses carefully schooled by your host, Sergio, and chosen for their surefootedness and gentle nature.

The Riding

The route known today as the Via Francigena follows the journey taken by Archbishop Sigeric in the year 990, as he travelled 1,800 km from Rome back to Canterbury after meeting Pope John XV. Over the centuries, countless pilgrims, merchants, and soldiers have followed these ancient tracks, adapting the route to the seasons, the weather, and the needs of their journeys.

On this trail, you’ll experience a section of this historic trail on horseback – just as many travellers once did. Each day offers between four and six hours in the saddle, winding through rolling hills, vineyards, olive groves, and medieval hamlets that seem frozen in time. The terrain varies from gentle open fields to forest paths and hilltop ridges, giving you plenty of opportunities for relaxed canters and long, scenic trots.

Your guide, Sergio, knows every stretch of the route and every horse personally. He carefully adjusts the pace and distance each day to suit the group’s experience and the horses’ comfort. The horses – responsive, surefooted, and well-schooled – make it easy to relax and enjoy the rhythm of the ride.

Level of Riding and Fitness

This trail is best suited to riders with at least an intermediate level of experience. You should feel confident and in control riding in open terrain at walk, trot and canter. A good level of current riding fitness is important, as you’ll spend around four to six hours in the saddle each day exploring the Tuscan countryside.

Guides and Group Size

Your host and guide for this holiday is Sergio, an experienced horseman with a deep knowledge of the Tuscan landscape and its rich history. His passion for both horses and heritage brings the Via Francigena to life, sharing stories and insights that make each day in the saddle truly memorable.

Group sizes are kept small (between 2 and 6 riders) to ensure a personal and relaxed experience. The maximum rider weight is 90 kg.

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The Horses

You’ll be riding well-cared-for, responsive horses that have all been personally trained by your host and guide. The herd includes a wonderful mix of breeds – elegant Quarter Horses, spirited English Thoroughbreds, graceful Arabians, athletic Anglo-Arabs, and hardy Sicilian natives – each perfectly suited to the varied terrain of the Tuscan countryside. Horses range from 14hh to 16hh.

Tack and Riding Equipment

Riders use a mix of English and Western saddles, all well-maintained and chosen for comfort over long hours in the saddle. This allows each rider to enjoy a style that suits their experience and preference. The riding is relaxed and natural, focused on connection and trust between horse and rider rather than formal schooling.

Accommodation and Dining

You’ll be staying at the Agriturismo La Selva, an ancient and typical Tuscan farmhouse. La Selva offers welcoming and comfortable rooms and apartments, all with private bathrooms, towels, hairdryers and WiFi. After returning from a day of riding on horseback, there is no better way to relax than a dip in the on site outdoor swimming pool or kick back in the serene garden with a book.

This is a fully inclusive holiday with all meals provided. Dinners are at La Selva and lunches on the trail are usually at local vineyards. You’ll enjoy delicious Italian cuisine and have the chance to taste the local wines.

Get a free Tuscany’s Via Francigena mini-brochure in PDF format.

Trail Booking Conditions

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Gallery

Itinerary

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.