Embark on a walking tour of Sicily, discovering the island’s breathtaking Mediterranean landscape and the fascinating ruins of its many ancient cultures.

The largest island in the Mediterranean, Sicily is an undeniable natural beauty that boasts a diverse blend of history and culture. Each town of this Italian island conveys a unique identity and character. Syracuse is a landscape of important Greek and Roman monuments, while in Monreale, you’ll discover Norman-French, Byzantine, and Arab influences. Trek the slopes of Mt. Etna, through fragrant forests and across corridors of hardened lava. Stay in sophisticated estates with lush gardens, ideal for a relaxing stroll. Fuel your walking tour of Sicily with Mediterranean meals, savoring the flavors of local olives, artichokes, nuts, and fruits. Join Country Walkers on one of best guided tours of Sicily and discover this land of long summers, ancient culture, and amazing cuisine.

Highlights

  • Stroll amid the ancient walls and columns of the Syracuse Archaeological Park with an expert historian, visiting the park’s famed Roman amphitheater along the way
  • Adventure across the slopes of Mt. Etna – Europe’s largest active volcano – hiking trails through wildflowers, and overtop a hardened lava flow
  • Stay vineyard-side at the Planeta Estate, savoring fine cuisine made from family recipes and sampling celebrated vintages of the estate’s own wine
  • Discover one of Sicily’s greatest cultural treasures, the Cathedral of Monreale, perched on the slope of Monte Caputo
On all Fully-Guided Adventures you can count on...
Icon of road-signs
Expert local guides to introduce you to the best of your destination.
Icon of map
Off-the-beaten-path places you’d never find on your own.
Icon of cutlery
Delicious, authentic multi-course meals — virtually all are included.
Icon of hikers
A maximum of 18 fun-loving fellow travelers to share the journey.
Icon of house
Gracious accommodations that are a clean, comfortable home away from home.
Icon of check-list
Experts to handle all the details.
Icon of airplane
Flight + Tour Combos include plane tickets, airport shuttles, and pre- and post-tour accommodations.

Itinerary

Fri, Mar 27 to Wed, Apr 8 - 2020

Show Itinerary:

Begin your adventure by departing from a convenient gateway city in the United States or Canada. Spend the first night aloft.

Upon your arrival at Catania’s Fontanarossa Airport, a representative holding a Country Walkers sign meets you after you exit the baggage-claim area at Bar Sicilia in the arrivals hall. A complimentary small-group transfer is provided to your hotel in Catania, approximately 30 minutes away. The remainder of the day is at your leisure (no meals included).

If you are going to be delayed meeting our transfer representative for more than 15 minutes due to delayed or lost luggage, please contact our One Call travel assistance to advise of your delay, and they will contact our transfer service on your behalf. Our drivers are generally able to wait for up to 45 minutes from the time your flight lands, after which you would be responsible for your own transfer.

Please note: If you arrive early, and your hotel room is not available prior to the designated check-in time, you may store your luggage with the reception desk.

Accommodation: UNA Hotel Palace, Catania

Aci Castello and Acireale; 3 miles, easy to moderate. Transfer to the slopes of Mt. Etna

Breakfast is included at your hotel. Your guide(s) meet you at your Catania hotel at 9:00 a.m. in the lobby. Your guide(s) will be wearing a Country Walkers shirt. Please be dressed for walking.

Depart Catania for the charming nearby coastal town of Aci Castello. Here, you’re greeted by the silhouette of an imposing, 11th-century castle, built on the foundations of a 7th-century Byzantine fortress. From its commanding position on a rocky cliff, this rugged castle once protected the Messina Strait. This is also a land of legend, as the rock formations in the seas beneath the castle are said to be rocks thrown by Cyclops at Ulysses in Homer’s Odyssey. Once an isolated promontory, the castle was connected to the mainland by lava flow from Mt. Etna in 1169. As the lava flow made other villages uninhabitable, the town of Aci Castello grew up around the base of the cliff, overlooking the shores of a beautiful bay. This spectacular setting has continued to inspire writers and artists for centuries.

Enjoy lunch at a seaside restaurant before continuing on to nearby Acireale, an elegant baroque city set on a series of lava terraces that lead to the sea. Long famous for its thermal waters, your walk begins in the town and continues to the sea, with a visit to a tiny church within a lava cave. Afterward, you drive toward Mt. Etna, whose majestic cone is the highest mountain in Sicily and one of the largest active volcanoes in Europe. Almost constant activity from the volcano has gifted its slopes with fertile soils for agriculture, orchards, and vineyards. You are the beneficiary of that gift this evening, as you arrive at your home for the night: a family-owned country boutique hotel set amid grapevines and citrus groves right on the slopes of Mt. Etna. Settle in, then gather for a welcome aperitivo, followed by a dinner of typical specialties

Accommodation: Zash Country Boutique Hotel & Spa, Archi/Riposto

2-4 miles, moderate to challenging, 800-ft. (maximum) elevation gain and loss

Following a delicious breakfast, begin your day with a short drive to the Rifugio Sapienza (at 6,348 feet) on Mt. Etna. Europe’s largest active volcano—over 11,000 feet high and occupying an area larger than metropolitan New York—the mountain presents a fascinating alpine environment with its combination of nature and the uncontrollable essence of fire. A range of walking routes (with a maximum elevation gain/loss of 800 feet) are weather- and volcano-dependent and may include a funivia (gondola) ride to the alpine station (at 9,514 feet) from where you have panoramic views over the southern promontory of Etna and the basin of Catania, as well as a view to the main summit of the mother volcano of Etna and Monti Silvestri, Monti Calcarazzi, and Montagnola—three side craters that are testament to the volcano’s activity. Alternatively, you may embark on an adventurous climb through pine forest, crossing a corridor of hardened lava flow. A simple lunch of Sicilian specialties is provided at the nearby rifugio (alpine refuge).

In the late afternoon, you return to your retreat on the slopes of Etna to relax poolside with a book or to stroll the estate before another delicious dinner of traditional Sicilian specialties.

Accommodation: Zash Country Boutique Hotel & Spa, Archi (Riposto)

4-7 miles, easy to moderate. Syracuse Archaeological Park; 1-2 hours, easy

Your day begins with a (two-and-a-half-hour) drive to one of the most beautiful spots in southeastern Sicily: the Oasi Nature Reserve at Vendicari, a complex of coastal marshes and a serene sandy beach. Depending on the season and time of day, the beach provides a protected home for large populations of migratory birds such as ducks, white egrets, black storks, and even European flamingos. Footpaths lead through the salt fields of the Pantano Grande to an abandoned tonnara (tuna factory) and the ruins of a Norman tower known as the Torre di Vendicari. From here, the view embraces the entire reserve, from the splendid isle of Vendicari to Capo Passero in the distance. Depending on the weather, you may be enticed to take a swim! Arriving on foot at a family-owned agriturismo (agricultural farm estate), you enjoy a meal of regional specialties, including grilled vegetables; local Sicilian provola, pecorino, and tuma cheeses; and freshly made pasta.

Following lunch, you continue on to Syracuse. At one time rivaling Athens as the most important and powerful city of the ancient world of Greater Greece, known as Magna Graecia, modern-day Syracuse is a UNESCO World Heritage site and the cultural and administrative capital of southeastern Sicily—an area known for its extravagant baroque architecture, historic ruins, gastronomic delights, beautiful landscapes, and beaches. Your first stop is the Parco Archeologico della Neapolis, where you enjoy a guided tour with a local expert. Syracuse’s Archaeological Park is a treasure trove of important Greek and Roman monuments, including the spectacular 5th-century BC Greek Theater, one of the finest and largest of its kind, still hosting Greek plays in the summer months. Nearby is the 2nd-century Anfiteatro Romano, the largest Roman amphitheater in Sicily and third-largest in Italy after the Colosseum in Rome and the amphitheater in Verona. Unlike the Greek Theater, the Roman Amphitheater bore witness to gruesome events, such as gladiator fights and slave punishments.

Late afternoon, you reach Ortigia, the historic heart of Syracuse and your home for the night. Upon settling into your room, set out for an evening of independent strolling and dining. You may wish to wander through the Piazza del Duomo, acclaimed as one of Italy’s most beautiful squares. At one time the acropolis of ancient Greek Syracuse, this elegant piazza is ringed by exquisite baroque buildings, constructed after the 1693 earthquake. Its centerpiece is the Duomo (cathedral), the city’s best example of the successions of evolving architectural styles that have shaped it over the centuries. The cathedral’s baroque facade disguises the 5th-century BC temple of Athena; however, 26 of the temple’s Doric columns remain intact and are visible both inside and outside.

Accommodation: Ortea Palace Luxury Hotel, Syracuse

4-7 miles, moderate, 1,000-ft. elevation loss

After an elaborate breakfast buffet of fruit, yogurt, fresh pressed juices, omelets, a variety of cured meats and cheeses, and distinctive Sicilian pastries like croissants with pistachio cream, you depart for one of Sicily’s most fascinating nature reserves and archaeological sites, the Necropolis of Pantalica. A plateau rising between the canyons of the Anapo and Calcinara rivers, it was inhabited from prehistoric times to the Middle Ages. The burial grounds carved in its steep rock walls comprise the largest complex of its kind in Sicily, with more than 5,000 tombs dating as far back as the second millennium BC. You walk through a dramatic river-carved landscape of limestone formations, luxuriant in colorful, fragrant Mediterranean vegetation.

Nearing midday, a short transfer delivers you to another traditional Sicilian lunch at a nearby family-owned restaurant and agriturismo. Dishes are derived from locally-sourced, seasonal ingredients and reflect the ancient traditions of the Anapo Valley. By mid-afternoon, you continue on a two-hour drive to the outskirts of Caltagirone, where you find your home away from home—a simple yet beautifully renovated Sicilian stone farmhouse located in the open countryside amid towering palms, olive trees, and neighboring forest. Following time to settle in to your room or relax by the outdoor pool, a feast of traditional specialties, perfectly paired with local Nero d’Avola red wine, is served in the warm, wood-beamed dining room.

Accommodation: Agriturismo Vecchia Masseria, Caltagirone

4 or 7 mile options, easy; 1-3 miles, easy

After awakening in the peaceful countryside and eating breakfast, you have the option of enjoying your inn’s facilities (including the Jacuzzi) or setting off on foot to neighboring Mount Ganzaria on one of two walks of varying distances. The mountain derives its name from the Arabic word for wild boar, yhanzaria, because of boars’ abundance on the mountain in ancient times. This area has been settled from the prehistoric age until the present. Your route includes a Byzantine necropolis and takes you through vegetation of cork oaks, eucalyptus, walnut groves, dwarf fan palms, and orchids, inhabited by foxes, porcupines, and weasels. Broad views on one side look over the Catanian plain and, on the other, toward southern Sicily.

Returning on foot to the masseria (farmhouse) for a light lunch, you then take leave of it and transfer a few miles to the magnificent Villa Romana del Casale, considered the most important Roman archaeological site in Sicily. This Roman villa or hunting lodge, now a UNESCO World Heritage site, was built around the 3rd and 4th centuries (AD) and is known for its extraordinary collection of mosaics, in various stages of restoration. Walkways take you through some of its 40 rooms that are carpeted with 4,200 square yards of magnificent mosaics depicting vivid scenes from mythology, hunting and fishing, and various aspects of everyday Roman life. Concluding your visit, you return to the estate for a relaxing evening and another delicious dinner.

Accommodation: Agriturismo Vecchia Masseria, Caltagirone

5 miles, easy to moderate

This morning transfer westward (two-and-a-half hours) to the Bosco della Ficuzza, a vast nature reserve with Royal Palace, commissioned by King Ferdinand I of Naples during his exile. Enjoy a scenic walk and picnic lunch as you traverse woodlands, home to hare, wild boar, and birds of prey. Continue on (two-hour drive) to the seaside town of Trapani. Named Drépanon, or “sickle,” by the Elymians for the curve of its harbor, Trapani claims a strategic position on Sicily’s west coast—which has made this major trading port a frequent site of conquest. Beyond the city, salt plains studded with windmills show lingering traces of its ancient salt trade, and Trapani also has a heritage of coral and tuna fishing. Today, Trapani province is a major source of wine, producing more even than the region of Tuscany. Settle into your hotel in the town’s historic center, then step out for dinner, perhaps savoring cuscus (couscous) and fresh-caught fish (reflecting the city’s North African influences) in a nearby favorite restaurant.

Accommodation: Badia Nuova Residence or La Gancia Residence, Trapani

5 miles, moderate

Departing Trapani, a 55-minute transfer delivers you to today’s walk in the Riserva Naturale dello Zingaro, Sicily’s first nature reserve, established in 1981 after a successful protest halted a road construction project. The reserve features well-maintained paths, panoramic sea views, and a large variety of rare and endemic plants and rich fauna including eagles, peregrine falcons, and lizards. The area is also home to the spectacular Uzzo Grotto, one of the first prehistoric settlements in Sicily. The walk is along an out-and-back coastal trail involving minimal elevation gain and loss but with some rocky sections (so the mileage can be adjusted accordingly).

Finishing up the walk, a 15-minute drive brings you to a nearby farm estate managed by Daniela Adamo, a graduate of the University of Gastronomic Sciences by Slow Food in Piedmont, who returned home to dedicate herself to the family business of olive oil production. Begin this special experience with an aperitivo on the terrace, followed by a lunch featuring ingredients from the organic garden and local producers. After the meal, learn how to prepare an espresso (or macchiato) and typical almond pastries or cassata, another Sicilian specialty.

You return to Trapani to enjoy an evening of independent exploration and dining, with restaurant suggestions from your guides.

Accommodation: Badia Nuova Residence or La Gancia Residence, Trapani

1 mile, easy and 1-3 miles, easy to moderate

This morning, you visit one of Italy’s most spectacular hill towns: Erice, set atop the legendary Mt. Eryx at 2,460 feet. On a clear day, there are panoramic views across the plains of Trapani, down the west coast of Sicily, and even to Cape Bon in Tunisia. Originally settled by the ancient Elymians, the town boasts a fascinating history and is an important historical site associated with fertility goddesses—the Carthaginians’ Astarte, Greeks’ Aphrodite, and Romans’ Venus. Arriving through a maze of medieval streets, tiny piazzas, churches, and baroque flowering balconies to Erice’s enchanting historic core, you set off on a walking tour of the medieval town and some of its important sites: the hilltop Norman Castello di Venere (Castle of Venus), which offers spectacular views, and the 14th-century main town church of Chiesa Madre and bell tower, constructed from stones from the ancient Temple of Venus on the same site. The majestic Norman castle was a massive fortification and the power seat of these 11th-century conquerors in western Sicily. Afterward, enjoy lunch at an agriturismo before reaching Segesta, which features a marvelous Doric temple. Dating to 430 BC and situated alone in a field, it is one of Italy’s best-preserved ancient temples. Founded by the Elymians, a mysterious ancient people, the city of Segesta was fought over for centuries before eventually being conquered by the Romans.

Another hour’s transfer brings you south to the countryside of Menfi and your home for the next two nights at a vineyard-side resort. The individually decorated guest rooms open onto private terraces with views over herb and flower gardens and vineyards. Following a welcome aperitivo, you proceed to a dinner of superlative cuisine served at a large communal table in the hotel’s dining room—accompanied, of course, by the estate’s renowned vintages.

Accommodation: Planeta Estate – La Foresteria, Menfi

3-5 miles, easy

After breakfast in your tranquil resort, you drive about 30 minutes to Selinunte, an ancient city that is now one of Sicily’s most dramatically sited Greek ruin complexes. This city, whose name is derived from the Greek word for celery, selinus, was one of ancient Greece’s most prosperous colonies as early as the 7th century BC, and hence the object of centuries of battles.

Following lunch, a leisurely afternoon at the hotel offers time to pack, relax, and perhaps swim in the hotel’s panoramic outdoor swimming pool. This evening, a short drive brings you to La Dispensa winery and vineyards, also owned by the Planeta Estate. Planted in nearly 300 acres of vines, the winery produces quality white and red wines, including the super cru Cometa and Segreta lines. Following a guided tour of the historic winery, you gather in the library, home to hundreds of books dedicated to the grapevine, for a tasting of Planeta wines paired with breadsticks, crostini, and olives. A farewell dinner follows on the outdoor terrace (weather permitting), a perfect venue for toasting your discoveries of enchanting Sicily. (Please note that, La Dispensa is closed on national holidays; therefore, some groups will dine at a fantastic seafood restaurant in Porto Palo di Menfi, just a few minutes from the hotel.)

Accommodation: Planeta Estate – La Foresteria, Menfi

After enjoying breakfast in Menfi, travel with your group to Monreale, whose cathedral is one of the greatest examples of Norman architecture in the world. Built between 1170 and 1189 by William II (in competition with a royal church then being built in Palermo), the cathedral today is one of nine Norman structures in Sicily inscribed together on the UNESCO World Heritage list and a National Monument in its own right. Craftsmen from Constantinople were enlisted to assist in creating the more than 64,500 square feet of magnificent, solid-gold, Byzantine mosaics for which the cathedral is renowned. As you explore this architectural masterpiece, consider how the mosaics, carvings, inlays, and pointed arches demonstrate a harmonious blend of Norman-French, Byzantine, and Arab cultures. Afterward, you transfer to nearby Palermo (arriving by 1:30 p.m.) for your post-tour night. (Lunch and dinner are on your own.)

Accommodation: Grand Hotel Piazza Borsa, Palermo, Italy

Ciao! This morning, a complimentary small-group transfer is provided to Palermo’s Falcone Borsellino Airport based on your departure time. (Your departure transfer time will be communicated to you on tour by your guides.)

Sun, Mar 29 to Tue, Apr 7 - 2020

Show Itinerary:

Aci Castello and Acireale; 3 miles, easy to moderate. Transfer to the slopes of Mt. Etna

Your guide(s) meet you at the UNA Hotel Palace at 9:00 a.m. in the lobby. Your guide(s) will be wearing a Country Walkers shirt. Please be dressed for walking.

Depart Catania for the charming nearby coastal town of Aci Castello. Here, you’re greeted by the silhouette of an imposing, 11th-century castle, built on the foundations of a 7th-century Byzantine fortress. From its commanding position on a rocky cliff, this rugged castle once protected the Messina Strait. This is also a land of legend, as the rock formations in the seas beneath the castle are said to be rocks thrown by Cyclops at Ulysses in Homer’s Odyssey. Once an isolated promontory, the castle was connected to the mainland by lava flow from Mt. Etna in 1169. As the lava flow made other villages uninhabitable, the town of Aci Castello grew up around the base of the cliff, overlooking the shores of a beautiful bay. This spectacular setting has continued to inspire writers and artists for centuries.

Enjoy lunch at a seaside restaurant before continuing on to nearby Acireale, an elegant baroque city set on a series of lava terraces that lead to the sea. Long famous for its thermal waters, your walk begins in the town and continues to the sea, with a visit to a tiny church within a lava cave. Afterward, you drive toward Mt. Etna, whose majestic cone is the highest mountain in Sicily and one of the largest active volcanoes in Europe. Almost constant activity from the volcano has gifted its slopes with fertile soils for agriculture, orchards, and vineyards. You are the beneficiary of that gift this evening, as you arrive at your home for the night: a family-owned country boutique hotel set amid grapevines and citrus groves right on the slopes of Mt. Etna. Settle in, then gather for a welcome aperitivo, followed by a dinner of typical specialties

Accommodation: Zash Country Boutique Hotel & Spa, Archi/Riposto

2-4 miles, moderate to challenging, 800-ft. (maximum) elevation gain and loss

Following a delicious breakfast, begin your day with a short drive to the Rifugio Sapienza (at 6,348 feet) on Mt. Etna. Europe’s largest active volcano—over 11,000 feet high and occupying an area larger than metropolitan New York—the mountain presents a fascinating alpine environment with its combination of nature and the uncontrollable essence of fire. A range of walking routes (with a maximum elevation gain/loss of 800 feet) are weather- and volcano-dependent and may include a funivia (gondola) ride to the alpine station (at 9,514 feet) from where you have panoramic views over the southern promontory of Etna and the basin of Catania, as well as a view to the main summit of the mother volcano of Etna and Monti Silvestri, Monti Calcarazzi, and Montagnola—three side craters that are testament to the volcano’s activity. Alternatively, you may embark on an adventurous climb through pine forest, crossing a corridor of hardened lava flow. A simple lunch of Sicilian specialties is provided at the nearby rifugio (alpine refuge).

In the late afternoon, you return to your retreat on the slopes of Etna to relax poolside with a book or to stroll the estate before another delicious dinner of traditional Sicilian specialties.

Accommodation: Zash Country Boutique Hotel & Spa, Archi (Riposto)

4-7 miles, easy to moderate. Syracuse Archaeological Park; 1-2 hours, easy

Your day begins with a (two-and-a-half-hour) drive to one of the most beautiful spots in southeastern Sicily: the Oasi Nature Reserve at Vendicari, a complex of coastal marshes and a serene sandy beach. Depending on the season and time of day, the beach provides a protected home for large populations of migratory birds such as ducks, white egrets, black storks, and even European flamingos. Footpaths lead through the salt fields of the Pantano Grande to an abandoned tonnara (tuna factory) and the ruins of a Norman tower known as the Torre di Vendicari. From here, the view embraces the entire reserve, from the splendid isle of Vendicari to Capo Passero in the distance. Depending on the weather, you may be enticed to take a swim! Arriving on foot at a family-owned agriturismo (agricultural farm estate), you enjoy a meal of regional specialties, including grilled vegetables; local Sicilian provola, pecorino, and tuma cheeses; and freshly made pasta.

Following lunch, you continue on to Syracuse. At one time rivaling Athens as the most important and powerful city of the ancient world of Greater Greece, known as Magna Graecia, modern-day Syracuse is a UNESCO World Heritage site and the cultural and administrative capital of southeastern Sicily—an area known for its extravagant baroque architecture, historic ruins, gastronomic delights, beautiful landscapes, and beaches. Your first stop is the Parco Archeologico della Neapolis, where you enjoy a guided tour with a local expert. Syracuse’s Archaeological Park is a treasure trove of important Greek and Roman monuments, including the spectacular 5th-century BC Greek Theater, one of the finest and largest of its kind, still hosting Greek plays in the summer months. Nearby is the 2nd-century Anfiteatro Romano, the largest Roman amphitheater in Sicily and third-largest in Italy after the Colosseum in Rome and the amphitheater in Verona. Unlike the Greek Theater, the Roman Amphitheater bore witness to gruesome events, such as gladiator fights and slave punishments.

Late afternoon, you reach Ortigia, the historic heart of Syracuse and your home for the night. Upon settling into your room, set out for an evening of independent strolling and dining. You may wish to wander through the Piazza del Duomo, acclaimed as one of Italy’s most beautiful squares. At one time the acropolis of ancient Greek Syracuse, this elegant piazza is ringed by exquisite baroque buildings, constructed after the 1693 earthquake. Its centerpiece is the Duomo (cathedral), the city’s best example of the successions of evolving architectural styles that have shaped it over the centuries. The cathedral’s baroque facade disguises the 5th-century BC temple of Athena; however, 26 of the temple’s Doric columns remain intact and are visible both inside and outside.

Accommodation: Ortea Palace Luxury Hotel, Syracuse

4-7 miles, moderate, 1,000-ft. elevation loss

After an elaborate breakfast buffet of fruit, yogurt, fresh pressed juices, omelets, a variety of cured meats and cheeses, and distinctive Sicilian pastries like croissants with pistachio cream, you depart for one of Sicily’s most fascinating nature reserves and archaeological sites, the Necropolis of Pantalica. A plateau rising between the canyons of the Anapo and Calcinara rivers, it was inhabited from prehistoric times to the Middle Ages. The burial grounds carved in its steep rock walls comprise the largest complex of its kind in Sicily, with more than 5,000 tombs dating as far back as the second millennium BC. You walk through a dramatic river-carved landscape of limestone formations, luxuriant in colorful, fragrant Mediterranean vegetation.

Nearing midday, a short transfer delivers you to another traditional Sicilian lunch at a nearby family-owned restaurant and agriturismo. Dishes are derived from locally-sourced, seasonal ingredients and reflect the ancient traditions of the Anapo Valley. By mid-afternoon, you continue on a two-hour drive to the outskirts of Caltagirone, where you find your home away from home—a simple yet beautifully renovated Sicilian stone farmhouse located in the open countryside amid towering palms, olive trees, and neighboring forest. Following time to settle in to your room or relax by the outdoor pool, a feast of traditional specialties, perfectly paired with local Nero d’Avola red wine, is served in the warm, wood-beamed dining room.

Accommodation: Agriturismo Vecchia Masseria, Caltagirone

4 or 7 mile options, easy; 1-3 miles, easy

After awakening in the peaceful countryside and eating breakfast, you have the option of enjoying your inn’s facilities (including the Jacuzzi) or setting off on foot to neighboring Mount Ganzaria on one of two walks of varying distances. The mountain derives its name from the Arabic word for wild boar, yhanzaria, because of boars’ abundance on the mountain in ancient times. This area has been settled from the prehistoric age until the present. Your route includes a Byzantine necropolis and takes you through vegetation of cork oaks, eucalyptus, walnut groves, dwarf fan palms, and orchids, inhabited by foxes, porcupines, and weasels. Broad views on one side look over the Catanian plain and, on the other, toward southern Sicily.

Returning on foot to the masseria (farmhouse) for a light lunch, you then take leave of it and transfer a few miles to the magnificent Villa Romana del Casale, considered the most important Roman archaeological site in Sicily. This Roman villa or hunting lodge, now a UNESCO World Heritage site, was built around the 3rd and 4th centuries (AD) and is known for its extraordinary collection of mosaics, in various stages of restoration. Walkways take you through some of its 40 rooms that are carpeted with 4,200 square yards of magnificent mosaics depicting vivid scenes from mythology, hunting and fishing, and various aspects of everyday Roman life. Concluding your visit, you return to the estate for a relaxing evening and another delicious dinner.

Accommodation: Agriturismo Vecchia Masseria, Caltagirone

5 miles, easy to moderate

This morning transfer westward (two-and-a-half hours) to the Bosco della Ficuzza, a vast nature reserve with Royal Palace, commissioned by King Ferdinand I of Naples during his exile. Enjoy a scenic walk and picnic lunch as you traverse woodlands, home to hare, wild boar, and birds of prey. Continue on (two-hour drive) to the seaside town of Trapani. Named Drépanon, or “sickle,” by the Elymians for the curve of its harbor, Trapani claims a strategic position on Sicily’s west coast—which has made this major trading port a frequent site of conquest. Beyond the city, salt plains studded with windmills show lingering traces of its ancient salt trade, and Trapani also has a heritage of coral and tuna fishing. Today, Trapani province is a major source of wine, producing more even than the region of Tuscany. Settle into your hotel in the town’s historic center, then step out for dinner, perhaps savoring cuscus (couscous) and fresh-caught fish (reflecting the city’s North African influences) in a nearby favorite restaurant.

Accommodation: Badia Nuova Residence or La Gancia Residence, Trapani

5 miles, moderate

Departing Trapani, a 55-minute transfer delivers you to today’s walk in the Riserva Naturale dello Zingaro, Sicily’s first nature reserve, established in 1981 after a successful protest halted a road construction project. The reserve features well-maintained paths, panoramic sea views, and a large variety of rare and endemic plants and rich fauna including eagles, peregrine falcons, and lizards. The area is also home to the spectacular Uzzo Grotto, one of the first prehistoric settlements in Sicily. The walk is along an out-and-back coastal trail involving minimal elevation gain and loss but with some rocky sections (so the mileage can be adjusted accordingly).

Finishing up the walk, a 15-minute drive brings you to a nearby farm estate managed by Daniela Adamo, a graduate of the University of Gastronomic Sciences by Slow Food in Piedmont, who returned home to dedicate herself to the family business of olive oil production. Begin this special experience with an aperitivo on the terrace, followed by a lunch featuring ingredients from the organic garden and local producers. After the meal, learn how to prepare an espresso (or macchiato) and typical almond pastries or cassata, another Sicilian specialty.

You return to Trapani to enjoy an evening of independent exploration and dining, with restaurant suggestions from your guides.

Accommodation: Badia Nuova Residence or La Gancia Residence, Trapani

1 mile, easy and 1-3 miles, easy to moderate

This morning, you visit one of Italy’s most spectacular hill towns: Erice, set atop the legendary Mt. Eryx at 2,460 feet. On a clear day, there are panoramic views across the plains of Trapani, down the west coast of Sicily, and even to Cape Bon in Tunisia. Originally settled by the ancient Elymians, the town boasts a fascinating history and is an important historical site associated with fertility goddesses—the Carthaginians’ Astarte, Greeks’ Aphrodite, and Romans’ Venus. Arriving through a maze of medieval streets, tiny piazzas, churches, and baroque flowering balconies to Erice’s enchanting historic core, you set off on a walking tour of the medieval town and some of its important sites: the hilltop Norman Castello di Venere (Castle of Venus), which offers spectacular views, and the 14th-century main town church of Chiesa Madre and bell tower, constructed from stones from the ancient Temple of Venus on the same site. The majestic Norman castle was a massive fortification and the power seat of these 11th-century conquerors in western Sicily. Afterward, enjoy lunch at an agriturismo before reaching Segesta, which features a marvelous Doric temple. Dating to 430 BC and situated alone in a field, it is one of Italy’s best-preserved ancient temples. Founded by the Elymians, a mysterious ancient people, the city of Segesta was fought over for centuries before eventually being conquered by the Romans.

Another hour’s transfer brings you south to the countryside of Menfi and your home for the next two nights at a vineyard-side resort. The individually decorated guest rooms open onto private terraces with views over herb and flower gardens and vineyards. Following a welcome aperitivo, you proceed to a dinner of superlative cuisine served at a large communal table in the hotel’s dining room—accompanied, of course, by the estate’s renowned vintages.

Accommodation: Planeta Estate – La Foresteria, Menfi

3-5 miles, easy

After breakfast in your tranquil resort, you drive about 30 minutes to Selinunte, an ancient city that is now one of Sicily’s most dramatically sited Greek ruin complexes. This city, whose name is derived from the Greek word for celery, selinus, was one of ancient Greece’s most prosperous colonies as early as the 7th century BC, and hence the object of centuries of battles.

Following lunch, a leisurely afternoon at the hotel offers time to pack, relax, and perhaps swim in the hotel’s panoramic outdoor swimming pool. This evening, a short drive brings you to La Dispensa winery and vineyards, also owned by the Planeta Estate. Planted in nearly 300 acres of vines, the winery produces quality white and red wines, including the super cru Cometa and Segreta lines. Following a guided tour of the historic winery, you gather in the library, home to hundreds of books dedicated to the grapevine, for a tasting of Planeta wines paired with breadsticks, crostini, and olives. A farewell dinner follows on the outdoor terrace (weather permitting), a perfect venue for toasting your discoveries of enchanting Sicily. (Please note that, La Dispensa is closed on national holidays; therefore, some groups will dine at a fantastic seafood restaurant in Porto Palo di Menfi, just a few minutes from the hotel.)

Accommodation: Planeta Estate – La Foresteria, Menfi

After a final relaxed breakfast, you transfer (90 minutes) to Monreale, (from monte reale, or “royal mountain”) situated on the slopes of Monte Caputo, amid picturesque groves of almond, orange, and olive trees. The town’s crowning glory is its cathedral, considered one of the finest examples of Norman architecture in the world. Built between 1170 and 1189 by William II (in competition with a royal church then being built in Palermo), the cathedral today is one of nine Norman structures in Sicily inscribed together on the UNESCO World Heritage list and a National Monument in its own right. Craftsmen from Constantinople were enlisted to assist in crafting the more than 64,500 square feet of magnificent, solid-gold, Byzantine mosaics for which the cathedral is renowned. As you explore this architectural masterpiece, consider how the mosaics, carvings, inlays, and pointed arches demonstrate a harmonious blend of Norman-French, Byzantine, and Arab cultures. You continue on to nearby Palermo (arriving by 1:30 p.m.), where you can conveniently explore this historic city on your own or make flight or rail connections for onward travels.

Linger Longer with a Tour Extension

Italy: Sicily
Pre-Tour

Pre-Tour Extension - Taoromina

  • Two nights at the Hotel Villa Schuler†
  • Small-group airport and hotel transfers
  • Two breakfasts

2 Nights From $498
per person, double occupancy

Please refer to your air itinerary for your specific flight details.

Upon your arrival at Catania’s Fontanarossa Airport, please retrieve your luggage and clear customs, then meet your driver at Bar Sicilia in the arrivals hall. A complimentary small-group transfer will be provided to your Taormina hotel. The remainder of the day is at your leisure (no meals included).

Accommodation: Hotel Villa Schuler

Today is yours to explore this chic resort town perched idyllically above the Mediterranean, with a history dating back millennia. Discover dreamy streets, medieval churches, and a beautifully preserved Greek theater. Later, you might relax at one of the spectacular beaches you can see from the city’s panoramic position high above the Ionian Sea and easily accessible by cable car. Your family-run hotel in the heart of the historic center, surrounded by its exotic gardens, gives you access to all the best of this beguiling city. (Lunch and dinner are on your own.)

Accommodation: Hotel Villa Schuler

After a relaxing breakfast at your hotel, a complimentary transfer from Taormina to your Catania hotel is scheduled for 2:00 p.m. A Country Walkers representative will meet you in the lobby of your Taormina hotel and assist you with your transfer.

Italy: Sicily 2
Post-Tour

Post-Tour Extension - Palermo

  • One night at the Grand Hotel Piazza Borsa
  • Small-group airport and hotel transfers
  • One breakfast

1 Night From $198
per person, double occupancy

Today is yours to explore more of this historical coastal town. Not to be missed is the spacious botanical gardens, praised by Goethe as “the most beautiful place on earth” nor the Massimo Theater, Italy’s largest indoor theater where the final scenes of The Godfather trilogy were filmed. After a full day of exploring, relax at your centrally located hotel with a massage or aperitivo before savoring your last Sicilian dinner. (Lunch and dinner are on your own.)

Accommodation: Grand Hotel Pizza Borsa

Ciao! This morning, a complimentary small-group transfer is provided to Palermo’s Falcone Borsellino Airport based on your departure time. (Your departure transfer time will be communicated to you on tour by your guides.)

What's Included

Flight + Tour Combo
Tour Only
Exceptional boutique accommodations Check Check
All on-tour meals except 2 dinners Check Check
Local guides with you throughout tour Check Check
Local wine and/or beer with dinner Check Check
Entrance fees and special events as noted in the itinerary Check Check
Travel assistance available 24/7 provided by One Call International Check Check
Roundtrip airfare Check
One extra night in Catania and one extra night in Palermo Check
Airport car service for arrival & departure Check
Pre- and post-tour breakfasts Check
Business-class upgrades available Check
Morocco: Marrakesh, Foothills of the High Atlas & Essaouira

Dates & Prices

Flight + Tour Combo

13 days. Includes round-trip international airfare, airport car service, additional hotel nights with included breakfast, and your tour.

Single Supplement: From $1,148

Departing From New York, NY (JFK)

Other departure cities available. Call our Tour Consultants for pricing.

Tour Only

10 days. Includes your tour only.

Single Supplement: From $898

Limited Availability

Fri, Sep 6 - Wed, Sep 18

$7,298

Reserve Online
Limited Availability

Sun, Sep 8 - Tue, Sep 17

$6,248

Reserve Online
Call Required

Fri, Sep 20 - Wed, Oct 2

$7,298

Request a Call
Call Required

Sun, Sep 22 - Tue, Oct 1

$6,248

Request a Call
Call Required

Fri, Oct 4 - Wed, Oct 16

$7,198

Request a Call
Call Required

Sun, Oct 6 - Tue, Oct 15

$6,148

Request a Call

Flight + Tour Combo

13 days. Includes round-trip international airfare, airport car service, additional hotel nights with included breakfast, and your tour.

Single Supplement: From $1,048

Departing From New York, NY (JFK)

Other departure cities available. Call our Tour Consultants for pricing.

Tour Only

10 days. Includes your tour only.

Single Supplement: From $748

Fri, Mar 27 - Wed, Apr 8

$7,198

Reserve Online

Sun, Mar 29 - Tue, Apr 7

$6,348

Reserve Online

Fri, Apr 17 - Wed, Apr 29

$7,398

Reserve Online

Sun, Apr 19 - Tue, Apr 28

$6,348

Reserve Online

Fri, May 1 - Wed, May 13

$7,498

Reserve Online

Sun, May 3 - Tue, May 12

$6,448

Reserve Online

Fri, May 15 - Wed, May 27

$7,498

Reserve Online

Sun, May 17 - Tue, May 26

$6,448

Reserve Online

Fri, Sep 4 - Wed, Sep 16

$7,498

Reserve Online

Sun, Sep 6 - Tue, Sep 15

$6,448

Reserve Online

Fri, Sep 11 - Wed, Sep 23

$7,498

Reserve Online

Sun, Sep 13 - Tue, Sep 22

$6,448

Reserve Online

Fri, Oct 2 - Wed, Oct 14

$7,398

Reserve Online

Sun, Oct 4 - Tue, Oct 13

$6,348

Reserve Online

Fri, Oct 16 - Wed, Oct 28

$7,398

Reserve Online

Sun, Oct 18 - Tue, Oct 27

$6,348

Reserve Online

Jump To:

Expert Local Guides

Experience your destination like an insider with people who call it home.