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ITALY

Explore Italy in every gallop

Italy is a rider’s dream. One day you’re winding through olive groves and vineyards in the hills of Tuscany, the next you’re crossing the mountains of Sicily from the north coast to the south, watching the landscapes shift as you go. You can dive into classical dressage, explore volcanic slopes near Mount Etna, or take on fast-paced trails through nature reserves full of wildlife.


Whether you’re staying at a stylish country estate or riding between coastal villages, the food is unforgettable, the horses are well-schooled and willing, and the scenery is pure magic. This is more than a riding holiday—it’s Italy at its most generous, from the saddle.

3 or 7 nights

FROM €920

All levels

A fantastic horse riding holiday in Italy, which combines horse riding through the beautiful Tuscan countryside with some of the best classical dressage training in Europe.

Tuscany Classical Dressage

4-7 nights

FROM €625

All levels

Perfect place to visit if you dream of horse riding through the beautiful Tuscan countryside in Italy. This is suitable for riders, non-riders, families and children.

Tuscany Castello Di Santa Cristina

7 nights

FROM €1,990

Intermediate to Advanced

An epic trail, which crosses the greenest and wildest part 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.

Sicily Madonie to Mount Etna

7 nights

FROM €1,990

Intermediate to Advanced

A fantastic adventure which allows you to cross Sicily on horseback, from the north coast and the seaside town of Cefalu down to the south coast and the beautiful coastal reserve of Torre Salsa.

Sicily North Coast to South Coast Trail

7 nights

FROM €2,060

Intermediate to Advanced

Discover the real Sicily from the saddle, on this fascinating ride through the Madonie Natural Park, which extends to approximately 40 thousand hectares and is home to more than 70% of the island’s wildlife.

Sicily Madonie Trail

7 nights

FROM €1,990

Intermediate to Advanced

Experience a true immersion in the heart of Sicily, a melting pot of ancient civilisations. This is a fascinating journey on which you discover the true depth and richness of the island’s history, culture and agricultural heartlands.

Deep Sicily Trail

7 nights

FROM €1,780

Intermediate to Advanced

A true insight into Sicilian rural life with beautiful and varied riding, including visits to a local vineyard, nearby villages, the breath-taking north coast, and a taste of the high Madonie Mountains.

A Taste of Sicily

14 nights

FROM €3,980

Intermediate to Advanced

A truly fantastic adventure, crossing Sicily from the Madonie Mountains through enchanting valleys and incredibly varied scenery to reach majestic Mount Etna and encircling the volcano.

Sicilian Odyssey Trail

Flexible

FROM €1,170

All levels

Surrounded by rolling hills, olive groves, and breathtaking Mediterranean landscapes, this countryside escape offers the perfect mix of horse riding, local culture, and relaxation.

Pippa's Paddock Sicily - 3 Itineraries
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FIND YOUR RIDING HOLIDAY

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