Sicily

Day 1: Arrival

Your Sicilian odyssey begins at Casa Il Bosco, a beautifully restored nineteenth-century country house tucked deep within the wild, rolling countryside of the Madonie Park. From its terraces, the island’s northern coastline and the distant Aeolian Islands spread out like a painted horizon. You’ll settle in, enjoy a dinner crafted from local produce, and breathe your first deep lungful of Sicily’s mountain air.

Day 2: Piano Battaglia

After breakfast, you’ll meet your horse for the journey and ride out at around 8.30am. The morning unfolds in a steady climb through Mediterranean scrub and woodland, with sweeping views over the Tyrrhenian Sea. The trail slips into forests of holm oak, cork and downy oak as you approach the territory of Isnello. After a picnic lunch, the ascent continues along the northern flanks of Pizzo Carbonara – Sicily’s second-highest peak at 1,979 metres – threading through lush oaks and beech until you reach Piano Battaglia, the mountain station at the heart of the Madonie. Dinner featuring local flavours awaits at Hotel Rifugio Marini, where you’ll spend the night.

Day 3: Agriturismo Feudo Catuso

This morning’s ride begins at 8.30am as you follow a route through the high mountains of the Madonie Park. Reaching lofty viewpoints, Sicily’s rugged interior unfurls beneath you. Descending towards the historic town of Polizzi Generosa, you’ll pause for a picnic lunch before continuing along ancient tracks through agricultural landscapes to Agriturismo Feudo Catuso – a restored thirteenth-century farmstead. Dinner is made with local produce, and you’ll spend the night in this peaceful rural haven.

Day 4: Agriturismo Mappa

Breakfast is followed by an 8.30am departure into the very centre of Sicily – a region long known as the island’s fertile “breadbasket.” This is a land stitched together by trazzere, the old Bourbon royal pathways that once ensured free passage for livestock and travellers across the island. Riding past the Sanctuary of Our Lady of Bilici, marking Sicily’s geographical centre, you continue towards Marianopoli station and into endless wheat and hay fields. Your destination is Mappa, once the country residence of the Princes of Spadafora and now a charming agriturismo with a swimming pool. Dinner and overnight here.

Day 5: Agriturismo Principe di Aragona

After breakfast, you’ll leave Mappa around 8.00am and ride through open fields towards Sutera, an ancient hilltop village considered one of the oldest continuously inhabited sites in human history. Following the pathways of the Monte Conca nature reserve, the landscape spills into the wide River Platani valley – one of western Sicily’s main waterways. A picnic lunch offers a moment to rest before the afternoon ride through woodland and farmland toward Agriturismo Principe di Aragona, a restored farmstead with a pool. Dinner and overnight here.

Day 6: La Casa di Bacco

The day begins at 8.30am with gentle riding through rolling agricultural country. By lunchtime you’ll reach the village of Joppolo Giancaxio for a picnic, before continuing towards Giardina Gallotti and through neat rows of vineyards and olive groves. Your home tonight is La Casa di Bacco, a wine estate surrounded by its own vines and complete with a swimming pool. You’ll have time to relax or join an optional excursion to the Valley of the Temples, before enjoying a generous dinner accompanied by the estate’s wines.

Day 7: Luna Minoica

After breakfast, you’ll ride out around 8.30am through the agricultural landscapes of Agrigento, framed by olive and almond groves. Views of the Mediterranean shimmer ahead as you stop for a picnic near Realmonte. The final stretch leads into the coastal reserve of Torre Salsa – one of the island’s most pristine, spectacular shorelines. Your trail concludes with hooves on sand as you reach the reserve’s secluded beaches. Dinner is served right on the beach, only a short stroll from Luna Minoica, your stylish hotel for the night.

Day 8: Departure

Enjoy breakfast before your transfer to the airport – still sandy-toed, saddle-sore in the best way, and full to the brim with Sicily’s magic.

Day 1: Arrival

Your adventure begins at Casa Il Bosco, a beautifully restored nineteenth-century country house tucked deep within the wild Madonie countryside. From its terraces, the island’s northern coastline and the distant Aeolian Islands stretch out in a breathtaking panorama. You’ll settle in, enjoy a dinner crafted from local ingredients, and fall asleep wrapped in complete mountain quiet.

Day 2: Casalvecchio

After breakfast, you meet your horse and set out from Casa Il Bosco at around 8.30am, easing into the rhythm of the trail. The morning begins with a steady climb through wild Mediterranean vegetation and shaded woodland, where sweeping views of the Tyrrhenian Sea unfold behind you.

The route skirts the edges of Castelbuono before leading you to a peaceful picnic spot beside an old water mill. Time here offers a chance to rest, refuel, and take in the quiet beauty of the landscape.

In the afternoon, the ride follows the valley of the River Pollina – one of Sicily’s most captivating and lesser-known regions. This is a wilder, more untouched corner of the island, where panoramic vistas stretch across rugged terrain and open countryside.

By late afternoon, you arrive at Agriturismo Casalvecchio, set on the boundary between the untamed landscapes of Madonie Park and the rolling agricultural heartland of Sicily. Dinner is a highlight here, with fresh, seasonal produce sourced directly from the farm, followed by an overnight stay in this peaceful rural setting.

Day 3: Sperlinga

The morning begins with a relaxed departure from Agriturismo Casalvecchio at around 8.30am, as you ride out through open pastures and along ancient pathways that wind towards the heart of Sicily. The landscape here feels expansive and timeless, with far-reaching views stretching across the island’s interior.

Your destination is the village of Sperlinga – a place unlike any other. Known for its remarkable troglodyte dwellings, many of which are still inhabited today, the village is crowned by a striking castle carved directly into the rock. You will pause here for a picnic lunch, with time to explore the village and step inside this extraordinary fortress.

A short afternoon ride brings you to Baglio San Pietro, a beautifully restored seventeenth-century farmstead set on the edge of Nicosia, one of the most important towns in the province of Enna. A swimming pool and peaceful surroundings offer the perfect setting to unwind, before gathering for dinner and an overnight stay.

Day 4: Agira

You’ll leave Baglio San Pietro this morning and ride out into the surrounding countryside. The trail soon descends into the valley of the Salso Cimarosa River, where the landscape feels wonderfully untouched. Riding alongside the river, you are immersed in unspoilt nature, framed by the rugged peaks of the Erean Mountains rising around you.

A picnic lunch awaits near the small town of Nissoria, offering a peaceful pause in the heart of this lesser-travelled region.

In the afternoon, the scenery shifts once more as you ride on through eucalyptus forests and rolling open countryside, gradually making your way towards the historic territory of Agira – deep in the heart of inland Sicily.

On arrival, the horses are left to rest for the night, and a short transfer takes you up into the old town of Agira, perched high above the surrounding landscape. Narrow cobbled streets and sweeping views set the scene for the evening ahead. Dinner and overnight are at Case al Borgo, a charming stay nestled within the village itself.

Day 5: Castello di Pietratagliata

This morning’s ride sees you cross rolling hills and travel through vast stretches of grain and forage fields. This is Sicily at its most expansive – quiet, open, and deeply rooted in the rhythms of the land.

After several hours in the saddle, you arrive at the remarkable Castello di Pietratagliata. Perched dramatically atop a jagged rock, this little-known castle dates back to at least the fourteenth century, its origins steeped in mystery and local legend. You will pause here for a picnic lunch, taking in the striking setting and far-reaching views.

The afternoon ride continues through agricultural countryside, climbing gently to reveal sweeping panoramas before leading you through the intriguing site of Monte Rossomanno. There is a sense of history and quiet intrigue here, woven into the landscape itself.

From here, sandy tracks carry you through woodlands of eucalyptus and pine, guiding you towards Agriturismo Bannata. This charming rural stay offers a welcoming pool and peaceful surrounds – the perfect place to unwind after a full day’s ride. Dinner is served here, followed by an overnight stay.

Day 6: Montagna di Marzo

You leave Agriturismo Bannata behind this morning as the trail winds through eucalyptus forests and into a series of quiet, forgotten valleys. This is a peaceful stretch of the ride, where the sense of remoteness deepens with every kilometre.

By late morning, you reach the archaeological site of Montagna di Marzo – a fascinating and little-known historical landmark set amid the hills. You will explore the site on horseback, before pausing nearby for a relaxed picnic lunch.

The afternoon unfolds across open countryside, with wide skies and gently rolling terrain guiding you onwards. Your destination is Agriturismo Il Mandorleto, a charming stay set within an old agricultural hamlet, renowned for its production of almonds – a cornerstone of Sicilian cuisine.

Dinner here showcases the region’s rich culinary heritage, followed by an overnight stay in this peaceful rural setting.

Day 7: Villa Romana del Casale

The day begins at around 8.30am as you ride out through rolling fields of wheat and hay, interspersed with quiet stretches of eucalyptus forest. The landscape feels soft and expansive here, with a gentle rhythm that carries you towards the Lake of the Olivo Dam.

You will pause nearby for a picnic lunch in the woods, a peaceful setting to rest before the afternoon unfolds.

From here, the trail descends through a scenic valley, leading you to one of Sicily’s most extraordinary historical treasures – the Villa Romana del Casale. Home to around 3,500 square metres of remarkably preserved fourth-century mosaics, this UNESCO-listed site offers a vivid glimpse into the island’s ancient past. Time is set aside to explore the villa and its intricate artwork.

A short ride on brings you to Torre di Renda, a charming hotel once used as the residence of the local bishop, set within the territory of the medieval town of Piazza Armerina. A swimming pool and relaxed surrounds invite you to unwind before dinner and an overnight stay.

Day 8: Departure

After breakfast, you’ll transfer to the airport with Sicily’s colours, scents and stories still swirling through your veins.

Day 1: Arrive

Your Sicilian journey begins at Casa Il Bosco, a lovingly restored nineteenth-century country house surrounded by the wild, rolling landscapes of the Madonie Park. From here, the north coast and the distant Aeolian Islands stretch out in a breathtaking panorama. Settle in, breathe deeply, and enjoy a dinner prepared with local ingredients before your first night in the mountains.

Day 2: Piano Battaglia

After breakfast you’ll meet your horse and ride out at around 8.30am, beginning with a steady climb through fragrant Mediterranean vegetation and woodland. The Tyrrhenian Sea glitters below as you cross into the territory of Isnello. Following a picnic lunch, you’ll ascend the northern slopes of Pizzo Carbonara — Sicily’s second-highest peak at 1,979 metres — riding through magnificent forests of oak, holm oak and beech. Your destination is Piano Battaglia, the mountain station at the heart of the Madonie Park. Dinner and overnight at Hotel Rifugio Marini.

Day 3: Agriturismo Mandragiumenta

This morning’s ride begins at 8.30am as you follow mountain trails deeper into the Madonie. High ridgelines offer your first glimpses into the vast Sicilian interior. Descending towards the historic town of Polizzi Generosa, you’ll pause for a picnic lunch before continuing along ancient pathways that wind through rolling farmland. By late afternoon you’ll reach Agriturismo Mandragiumenta, where a locally sourced dinner and a peaceful night’s rest await.

Day 4: Villa Dafne

You’ll leave around 8.30am, riding into Sicily’s storied agricultural heartland — the island’s “breadbasket” since antiquity. This is a country etched with trazzere, the ancient Bourbon pathways once used to move livestock across the island. The day’s highlight is the remarkable caves of Gurfa, linked to the legend of Minos, King of Crete, and used variously as temples, grain stores, luxury lodgings and stables over the centuries. After a picnic lunch near this extraordinary site, you’ll continue into the territory of Alia and arrive at Villa Dafne, complete with a swimming pool. Dinner and overnight here.

Day 5: Case Javuti

Set off around 8.00am along trazzere and quiet country lanes, eventually reaching the San Leonardo River — often fast-flowing and sometimes challenging after heavy rain. You’ll follow the valley towards the Rosamarina dam, where you’ll stop for a picnic lunch. The afternoon brings a climb into the Calamigna mountains, a rugged and imposing range that frames this region. Your resting place tonight is Agriturismo Case Javuti, a peaceful rural retreat. Dinner and overnight.

Day 6: Gorgo del Drago

After breakfast you’ll begin with a steep, rewarding climb up Pizzo Trigna (1,297 metres), where a vast panorama of north-western Sicily unfurls beneath you. Descending the southern slopes, the trail leads across the agricultural landscapes of Baucina and Ciminna before reaching Mezzojuso for lunch. In the afternoon you’ll continue towards Godrano and on to Agriturismo Gorgo del Drago, set beside the Ficuzza woods and facing the dramatic bulk of Rocca Busambra, the highest peak in western Sicily. Dinner featuring local produce and overnight.

Day 7: Chiosi Country Club

Your final day begins with a beautiful ride through the Ficuzza woods — almost 7,400 hectares of protected forest established in 1799 as the personal hunting reserve of King Ferdinand. After passing through the village of Ficuzza and its nineteenth-century Royal Palace, you’ll stop for a picnic lunch before continuing through fields towards the town of Corleone. The last stretch leads to Chiosi Country Club, where dinner, a comfortable night’s rest and the quiet satisfaction of completing your Sicilian crossing await.

Day 8: Departure

After breakfast, you’ll be transferred to the airport — saddle-sore in the best way, and carrying a week’s worth of Sicily in your heart.

Day 1: Arrival

Your Sicilian escape begins at Casa Il Bosco, a beautifully restored nineteenth-century country house cocooned in the wild, whispering landscapes of the Madonie Park. From here, the island’s north coast and the distant Aeolian Islands stretch out in a breathtaking panorama. Settle into the quiet rhythm of the countryside and enjoy a dinner crafted from local produce before a restful first night.

Day 2: Rocca di Gonato

After breakfast you’ll meet your horse and ride out around 8.30am, beginning with a steady climb through fragrant Mediterranean vegetation and woodland. Sweeping views of the Tyrrhenian Sea unfold beneath you as the trail leads towards charming Castelbuono, where you’ll stop for a picnic lunch. The afternoon ride continues through open countryside towards Rocca di Gonato, a beautiful agriturismo with a swimming pool at the foot of the high Madonie Mountains. Dinner made from local produce and overnight here.

Day 3: Piano Battaglia

Today begins with a ride through quiet woods towards Piano Pomo, home to the extraordinary giant holly trees — a botanical peculiarity still not fully understood, towering far above typical holly specimens. From here, a panoramic trail carries you into the Pomieri area, where you’ll stop for a picnic lunch beneath wide skies. The afternoon is a gentle climb into the high Madonie Mountains, arriving at Piano Battaglia (1,600 metres), a mountain station at the heart of the park. Dinner and overnight at Hotel Rifugio Marini.

Day 4: Monte Cervi

After breakfast you’ll visit the Battaglietta, a high-mountain karst sinkhole where snowmelt gathers before running underground to the sea. Then the climb begins towards Pizzo Carbonara (1,979 metres), Sicily’s second-highest peak. Wild deer and goats are often spotted grazing here, and on clear days you can see Etna to the east, Rocca Busambra to the west, Monte Cammarata to the south and the Aeolian Islands to the north. A picnic beneath the imposing Serra della Quacella follows, before you continue across high pastures and into the forests of Monte Cervi. Return to Hotel Rifugio Marini for a second night.

Day 5: Casalvecchio

You’ll ride out around 8.30am along remote paths through the heart of the Madonie, a region where wild boar, deer and birds of prey are often seen. Lunch awaits at Portella Mandarini, once a key crossroads for ancient transhumance routes. The afternoon takes you along rarely travelled pathways on the northern side of Pizzo Catarineci, offering spectacular views towards central Sicily and the medieval towns of Petralia Soprana and Gangi. By day’s end you’ll reach Agriturismo Casalvecchio, tucked deep into the countryside, where you’ll enjoy a farm-fresh dinner and a peaceful night.

Day 6: Geraci Siculo

This morning’s ride follows the valley of the River Pollina — a remote, magnificent area barely touched by tourism. After a picnic in a tiny, forgotten village, you’ll climb towards Geraci Siculo, a majestic medieval settlement dominated by its ruined castle. Once the seat of the powerful Ventimiglia Barons, Geraci’s narrow lanes and lofty position make it one of the gems of the Madonie. Dinner and overnight at Hotel Donna Vi, complete with spa facilities.

Day 7: Casa 'Il Bosco'

After breakfast, you’ll ride through the heart of Geraci Siculo before descending into a beautiful cork-oak forest. The trail passes close to Castelbuono, where you’ll pause for a picnic beside an old abandoned water mill. The final stretch leads you home along panoramic, fragrant pathways threading through olive groves, vineyards and dense Mediterranean brush. Back at Casa Il Bosco, a delicious farewell dinner awaits.

Day 8: Departure

Breakfast and transfer to the airport — hearts full, legs well-used, and Sicily now firmly under your skin.

Day 1: Arrival

Your Sicilian escape begins at Casa Il Bosco, a beautifully restored nineteenth-century country house tucked deep within the wild Madonie countryside. The views spill across the island’s northern coastline to the distant Aeolian Islands — a breathtaking welcome to the days ahead. Settle in, breathe in the mountain air, and enjoy a welcome dinner prepared from local produce.

Day 2: Sanctuary of Gibilmanna & Pizzo Sant’Angelo

After breakfast you’ll saddle up and ride out into the hills above Cefalù, climbing steadily towards Pizzo Sant’Angelo — the highest peak in the territory at 1,081 metres. On a clear day, the panorama stretches from the towering Madonie Mountains to the Tyrrhenian coastline and all the way to the Aeolian Islands shimmering offshore. A picnic lunch is followed by a visit to the Sanctuary of Gibilmanna before you ride back to Casa Il Bosco for a generous dinner showcasing the flavours of the region.

Day 3: Wine Tasting at Abbazia Santa Anastasia

Today’s ride follows an ancient trazzera, one of the historic Bourbon-era pathways that once carried livestock across the island. With the high Madonie peaks on the horizon, you’ll make your way towards Castelbuono before arriving at Abbazia Santa Anastasia — a restored Benedictine abbey now home to one of Sicily’s most esteemed vineyards. A guided cellar tour, wine tasting and light lunch await, before you ride back to Casa Il Bosco in the afternoon.

Day 4: Cefalù

This morning brings a true taste of Sicilian rural life as you ride to a local farm to see how artisans craft ricotta and traditional cheeses. The return journey takes you along one of the most panoramic ridgelines of Cefalù’s territory, with sweeping views towards Palermo on one side and the Nebrodi Mountains on the other. In the late afternoon, you’ll head down to the enchanting coastal town of Cefalù for a guided walk through its historic centre, followed by a seafood dinner right on the water’s edge.

Day 5: Madonie Mountains

After breakfast you’ll begin a two-day mountain adventure. The morning opens with a steady climb through wild Mediterranean scrub and oak woodland, framed by long views of the Tyrrhenian Sea. After a picnic lunch, you’ll ascend the northern slopes of Pizzo Carbonara — Sicily’s second-highest peak — riding through magnificent forests of oak, holm oak and beech. Your destination is Piano Battaglia, the mountain station at the heart of the Madonie Park. Dinner and overnight at Rifugio Marini.

Day 6: Isnello

Before leaving the high mountains, you’ll visit the Battaglietta — a natural depression where meltwater gathers before travelling underground to Cefalù. The trail then begins its descent through beautiful woodlands towards the territory of Isnello. After a picnic lunch, you’ll ride back towards the coast through wild, unspoilt vegetation with sweeping views over the north shore. Dinner awaits back at Casa Il Bosco.

Day 7: Sant’Ambrogio Beach

Your final ride leads through fragrant Mediterranean vegetation and quiet country lanes to the seaside village of Sant’Ambrogio. Here you’ll visit a local oil press for an olive-oil tasting before continuing to the beach. Weather and season permitting, you’ll bring the horses down onto the sand and enjoy a relaxed beach picnic. In the afternoon, you’ll ride back to your base for a delicious farewell dinner.

Day 8: Departure

After breakfast, you’ll transfer to the airport — soul full, senses awakened, and Sicily forever under your skin.