Horse Riding Holidays in Italy
Experience the incredible biodiversity of Italy on these unforgettable week-long horse riding holidays. Discover the greenest and most rugged parts of the island on the Wild Sicily – Madonie to Etna trail which will take you through the wildest parts of Sicily. The endless views and ever-changing scenery will take your breath away as you make your way towards the magnificent Mt Etna. Or book onto our Etruscan trail in Tuscany for a true Western experience, riding through woodlands and vineyards, following the banks of the river Fiori and swimming in lakes and rivers along the way.
Chianti Hills Trail
This riding holiday in Chianti offers a unique way to explore the Tuscan countryside just outside Siena, with its rolling hills, vineyards, olive groves, and charming medieval villages. As you ride through the picturesque landscape, you’ll pass by historic castles and abbeys, often with stops to enjoy the region’s renowned wine and cuisine. The small group size and knowledgeable owner guide ensure a personal experience, while the willing and responsive horses are the perfect partner to discover this enchanting part of Tuscany which has inspired poets, artists, and travellers for generations.
Tuscany’s Via Francigena
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.
Coast to Coast
A fantastic adventure which allows you to cross Sicily on horseback, from the north to the south coast. This trail offers unparalleled immersion in Sicily’s complex history and agricultural heritage, its magic and its legends.
Tuscany Short Break
Head to this 17th century castle and indulge in riding, swimming and wine tasting on this short break in Tuscany. Explore the charm of this region, crossing vast, unspoiled territory, dotted with lakes, traditional villages, palaces and vineyards.The castle offers the perfect location for exploring the south of Tuscany, nestled inbetween the neighbouring historic towns of Orvieto, Sorano, Pitigliano and Bolsena.
Brigands Trail
Explore the charm of Tuscany, crossing vast, unspoiled territory without restrictions. Riding alongside lakes and through local villages, your Italian guides at this family-run castle will lead you along some of the hidden trails used by the “Brigands” (outlaws) to escape 200 years ago. The riding on this trail is at all paces so you’ll need to be confident cantering in a group on a well schooled horse.
From the top of the castle tower there are 360-degree views across three regions – Lazio, Umbria and Tuscany. This is a vast 250-hectare estate and the land includes woods, gardens with olive trees, and of course incredible riding trails. Alongside the castle is the internationally renowned equestrian centre, with a stable of well trained horses.
Short on time? Take a look at the Tuscany Short Break.
Etruscan Trail Tuscany
Ride the ancient Etruscan pathways and discover this little visited corner of Southern Tuscany. Ride across breath-taking mountain pastures, follow the banks of the river Fiora and find your way through the area’s mysterious sunken roads cut deep into the rock over 2,000 years ago.
Wild Sicily – Madonie to Etna
Experience this epic trail which crosses the greenest and wildest parts of Sicily, setting off from the eastern Madonie Mountains and crossing the wooded Nebrodi Mountains to arrive at Mount Etna, one of the world’s most active volcanoes.
A challenging trail
Italy is an unparalleled destination for a horse riding holiday. Whether you want spectacular nature, panoramic views, Western riding or riding on the black craters of Mt Etna we will have a horse riding holiday to suit you. All our riding holidays feature full days in the saddle, excellent local food, navigating your horse through stunning scenery and enjoying some canters along the way.
Get pampered by the Italian hospitality
Your guides are experts on Italian history, culture and nature and will do their absolute best to make sure you have the horse riding holiday you’ve always dreamed of. Horses are well-mannered and a pleasure to ride. The accommodation during the trail will be in local Agriturismi, B&Bs and good quality hotels. Every day starts with a light breakfast before starting your riding journey. The support vehicle will provide a lovely, fresh picnic lunch of local produce and Italian specialities. Dinner is plentiful with multiple courses and will be served onsite at your accommodation or at a nearby restaurant.