Italy: Sicily

3 miles, easy to moderate

After enjoying an included breakfast at your hotel, your guides meet you in the lobby of your Palermo hotel at 8:30 a.m. They’ll be wearing Country Walkers shirts. Please be dressed for walking.

Departing Palermo, an hour (to 75-minute) drive delivers you to the trailhead and the first of many magnificent archaeological sites, Segesta. Dating to 430 BCE and situated alone in a field amongst Mediterranean macchia (shrubbery) and wildflowers, it is one of Italy’s best-preserved ancient temples. It features a marvelous Doric temple. Founded by the Elymians, a mysterious ancient people, the city of Segesta was fought over for centuries before eventually being conquered by the Romans. Discover the area on foot, taking in the atmosphere of this spectacular setting.

Finishing up the walk, a short drive brings you to a nearby farm estate (or baglio) 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, enjoy an espresso (or macchiato) while you learn how to prepare typical almond pastries or cassata, another Sicilian specialty.

This afternoon you continue 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 (or by the famous salt flats), then gather for a welcome aperitivo, followed by dinner, perhaps savoring cuscus (couscous) and fresh-caught fish (reflecting the city’s North African influences).

Included Meals: Breakfast, Lunch, Dinner

4-8 miles, moderate and 1 mile, easy

Departing Trapani, a 45-minute transfer delivers you to today’s walk in the Riserva Naturale di Monte Cofano, a towering limestone promontory jutting out between the turquoise Gulfs of Bonagia and Cofano. The reserve features well-maintained paths (your guides will review walk options prior to reaching the reserve), panoramic sea views, secluded bays, steep cliffs, and diverse flora and fauna. The landmark headland is also home to historic watchtowers, immense caves, and archaeological sites of prehistoric settlement. Finishing up the walk, a 10-minute drive brings you to lunch featuring western Sicilian cuisine in the neighboring town of Custonaci.

Afterward, 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.

A 90-minute journey south brings you to the countryside of Menfi and your home for the next two nights at a splendid 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.

Included Meals: Breakfast, Lunch, Dinner

3-5 miles, easy

After a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries and bread, and of course a cappuccino (or espresso), served 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 BCE, and hence the object of centuries of battles.

Following lunch, your guides may offer an easygoing hour-long optional walk above the hotel or a trail close to the seaside, or you may choose to enjoy a leisurely afternoon at the hotel to relax, and perhaps swim in the hotel’s outdoor swimming pool. This evening, you gather for another special dinner featuring the bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

2-4 miles, easy to moderate

After savoring breakfast at your hotel, drive southeast (approximately 60 minutes) to Riserva Naturale Orientata Torre Salsa, a nature reserve created in 1996 and managed by the World Wildlife Fund, it boasts a unique combination of hills, cliffs, sand dunes, fields and wetlands that are home to a variety of flora and fauna, including peregrine falcons, kestrels and horned owls as well as caretta caretta turtles. Enjoy a scenic walk (options along the park’s well-marked trails will be reviewed by your guides depending on the weather and fitness level of the group).

Afterward, continue to nearby Siculiana, a tiny village whose origins date back to the 10th century BCE, where you refuel over lunch of antipasti di mare or appetizers “from the sea” and other local specialties prior to continuing northeast for a two-hour drive to the outskirts of Caltagirone, where you find your next 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 into your room or relax by the outdoor pool, a feast of traditional dishes, perfectly paired with local Nero d’Avola red wine, is served in the warm, wood-beamed dining room.

Included Meals: Breakfast, Lunch, Dinner

1-2 miles, easy and 4 miles, moderate

After awakening in the peaceful countryside and eating breakfast, you set off (on a 30-minute drive) to the magnificent Villa Romana del Casale, considered the most important Roman archaeological site in Sicily. This Roman villa, or hunting lodge, is a UNESCO World Heritage site that was built around the 3rd and 4th centuries (AD). It is known for its extraordinary collection of mosaics in various stages of restoration. Walkways take you through some of its 40 rooms carpeted with 4,200 square yards of magnificent mosaics depicting vivid scenes from mythology, hunting and fishing, and scenes of everyday Roman life. Concluding your visit, you travel (90 minutes) to one of Sicily’s most fascinating nature reserves and archaeological sites, the Necropolis of Pantalica, stopping en route for lunch, comprised of dishes that are derived from locally sourced, seasonal ingredients reflecting the ancient traditions of the Anapo Valley.

Pantalica is a plateau rising between the canyons of the Anapo and Calcinara rivers, and 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 BCE. You walk through a dramatic river-carved landscape of limestone formations, luxuriant in colorful, fragrant Mediterranean vegetation.

Late afternoon, you continue to Syracuse. At one time this city rivaled Athens as the most powerful city 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, historical ruins, gastronomic delights, beautiful landscapes, and beaches. Your home for two nights is in Ortigia, the historical heart of Syracuse. Upon settling into your room, you 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. Ringed by exquisite baroque buildings constructed after the 1693 earthquake, the plaza’s 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 BCE temple of Athena; however, 26 of the temple’s Doric columns remain intact and are visible both inside and outside.

Included Meals: Breakfast, Lunch

5 miles, easy to moderate and 1 mile, easy

Start today with an elaborate breakfast of fruit, yogurt, fresh-pressed juices, omelets, cured meats and cheeses, and Sicilian pastries with pistachio cream enjoyed on the hotel’s panoramic rooftop terrace. Then, you depart for one of the most beautiful spots in southeastern Sicily—the Oasi Nature Reserve at Vendicari, a complex of coastal marshes with 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.

After lunch, travel by minibus to 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 of its kind, it still hosts Greek plays in the summer months. Nearby, is the 2nd-century Anfiteatro Romano, the largest Roman amphitheater in Sicily and third-largest in Italy. Unlike the Greek Theater, the Roman Amphitheater bore witness to gruesome events, such as gladiator fights and slave punishments. Late afternoon, you return to Ortigia, where you enjoy another relaxing evening on your own.

Included Meals: Breakfast, Lunch

Milo to Zafferana Etnea; 5 miles, moderate to challenging, 500-ft. elevation gain and 1,900-ft. elevation loss

Following a delicious breakfast, you depart Syracuse for Mt. Etna, whose majestic cone is the highest mountain in Sicily and one of the largest active volcanoes in Europe. Over 11,000 feet high and occupying an area larger than metropolitan New York, the mountain presents a fascinating alpine environment with a combination of nature and the uncontrollable essence of fire. Walk options today are again weather- and volcano-dependent and may include a trail along the Sentiero delle Ginestre (the Broom Route) from the village of Milo to Zafferana Etnea, through an area of chestnut forest, old shepherd settlements, the famous giant broom trees, and even a live oak that is over 700 years old. A sustained descent brings you to Zafferana Etnea, an important crossroads in the Roman era along the inland route that connected Catania with Taormina.

Almost constant activity from this volcano has gifted its slopes with fertile soils for agriculture, orchards, and vineyards, and midday finds you at one of the many emerging wineries on Etna’s slopes, where you’re treated to a light lunch and tasting. The location affords excellent views of the vineyards on one side and the volcano on the other.

Following lunch, continue to a family-owned country boutique hotel set amid grapevines and citrus groves. Settle in, and enjoy a leisurely afternoon at the hotel offers time to pack, relax, and perhaps swim in the hotel’s outdoor swimming pool. This evening, you gather for a special dinner paired with a glass (or two!) of wine from nearby vineyards—perfect for toasting your discoveries of enchanting Sicily.

Included Meals: Breakfast, Lunch, Dinner

After savoring breakfast at your hotel, bid farewell to your tour guides and travel companions and enjoy a final day relaxing at your resort, or exploring nearby Catania on your own.

Lunch and dinner are on your own today. If you plan to have dinner at the hotel’s Michelin-starred restaurant, please ensure that you book directly with the hotel a week in advance as a table cannot be guaranteed otherwise. We provide detailed city information on nearby Catania to help you plan your exploration should you choose to visit the island’s second largest city.

Included Meals: Breakfast

3-4 miles, easy to moderate, 500-ft. elevation gain and loss

After enjoying an included breakfast at your hotel, your guides meet you in the lobby of your Taormina hotel at 9:00 a.m. They’ll be wearing Country Walkers shirts. Please be dressed for hiking (with appropriate footwear and backpack).

Departing Taormina, a short drive delivers you to your first trailhead on the quiet, picturesque northern slopes of Mt. Etna, whose majestic cone is the highest mountain in Sicily and one of the largest active volcanoes in Europe. Over 11,000 feet high and occupying an area larger than metropolitan New York, the mountain presents a fascinating alpine environment that combines the beauty of nature and the uncontrollable essence of fire. Hiking options on the volcano’s quiet, picturesque northern slopes today are weather- and volcano-dependent and may include an adventurous climb to the recently formed craters of Monte Nero and the Bottoniera, or through Linguaglossa pine forest, crossing a corridor of lava flow. (Maximum altitude for the walk is approximately 7,000 feet.) Weather permitting, you are treated to a Sicilian-style picnic lunch of crusty bread, sun-dried tomatoes, fruit, cured meats, and local cheeses enjoyed trailside or at a rifugio (alpine hut).

This afternoon you travel to your nearby home-away-from-home for the next two nights: a family-owned country boutique hotel set amid grapevines and citrus groves. Settle in, then gather poolside for a welcome aperitivo, followed by a delicious dinner in the hotel’s Michelin-starred restaurant featuring elegant, refined Sicilian fare, paired with a glass (or two) of wine from the nearby fertile slopes.

Included Meals: Breakfast, Lunch, Dinner

5 miles, moderate to challenging, 500-ft. elevation gain and 1,900-ft. elevation loss

Following a delicious breakfast, begin your day with a drive to Mt. Etna’s picturesque eastern slopes. Hiking options today are again weather- and volcano-dependent and may include a trail along the Sentiero delle Ginestre (or the Broom Route) from the village of Milo to Zafferana Etnea, trekking through an area of chestnut forest and passing old shepherd settlements, the famous giant broom trees, and even a live oak that is over 700 years old. A sustained descent brings you to Zafferana Etnea, an important Roman-era crossroads that connected Catania with Taormina.

Almost constant activity from this volcano has blessed its slopes with fertile soils for agriculture, orchards, and vineyards. Midday, you arrive at one of the many emerging wineries on Etna’s slopes, where you’re treated to a light lunch and tasting. Its location affords excellent views of the vineyards on one side and the volcano on the other. You return to your country house hotel with time to relax and refresh prior to stepping out for another dinner that reflects the bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

3-4 mile options, easy to moderate, 500-ft. elevation gain and loss

Awaken at your tranquil resort to a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries and bread, and of course a cappuccino (or espresso). Then travel about 60 minutes to your trailhead outside Militello in the Val di Catania. Along with seven other nearby towns, Militello was gorgeously rebuilt in stunning Late Baroque style after a devastating 1693 earthquake, earning much of the Val di Noto status as a UNESCO World Heritage site for its architectural splendor. Today, Militello is celebrated for its fragrant orange groves, traditional mulled wine, and prickly pear cakes. From here, you set out on a scenic trail to the spectacular Cascate dell’Oxena, or Oxena River Waterfalls. Your pathway follows the canyon-like course of the river along basalt rocks formed by ancient volcanic eruptions. Luxuriant stands of olivastri, elms, ash trees, oaks, prickly pears, carob trees, tamarisks and oleanders mark your progress and you’ll have opportunities to take a refreshing dip in the river’s natural pools.

Refuel over a simple lunch of Sicilian specialties, like arancine—or seasoned rice balls with meat, fish, or eggplant, mushrooms and spinach—before continuing to your next destination. Following lunch, travel approximately to the valley of Noto, where the town of Ragusa is perched on a limestone hill. Ragusa Ibla, the Old Town, shared in the remarkable Baroque building boom at the turn of the 18th century, and you’ll have time to explore it up close tomorrow. Your accommodations in a former palace put you close to the spectacular Old Town. Providing an elegant mix of modernity and tradition, the hotel was skillfully refurbished to preserve its historic character while melding harmoniously with modern design. Dinner is on your own this evening; your guides will provide recommendations of the area’s best restaurants.

Included Meals: Breakfast, Dinner

3-5 miles, easy to moderate (with challenging sections), 600-900-ft. maximum elevation gain and loss, and 1-2 miles, easy

After savoring a breakfast of traditional local products in the fresh, clean air of your hotel’s elegant patio, head out for a hike along scenic pathways along the Cava della Misericordia, the Cave of Mercy. Your trail through pine, poplar, and oak forest leads you along an ancient quarry where evidence of human settlement has been left behind. Pass the Church of St. Elia, dedicated to the saint who many believed brought droughts to an end. Pause at an old Ibleo Byzantine cemetery, where some 3,000 souls were laid to rest. See the ruins of old mills and houses. And, finally, arrive at the Hermitage of Our Lady of Mercy, an ancient Benedictine Monastery built into the rocky landscape.

After, head to a nearby agriturismo (an agricultural farm estate), where a lunch of local specialties awaits. Enjoy farm-fresh ingredients and home-prepared specialties like Ragusan scacce, thin sheets of dough filled with spinach, ricotta, tomato and onion or eggplant and parsley.

Continue to Ragusa Ibla, where there’ll be time to explore this jewel with your guides. Stroll among its magnificent architecture—part of the final blossoming of European Baroque. Pause for a visit to an artisan studio to learn about the tradition of the Carretti Siciliani, the famed Sicilian horse carts adorned with elaborate paintings that depicted the local ideals of chivalry, faith, honor, and justice.

Continue exploring on your own, or maybe return to the hotel and treat yourself to time in the wellness center. Indulge in a massage, Turkish bath with aromatic oils, indoor salt water pool, and more. You may also enjoy the garden and outdoor pool at the nearby sister property. Reunite later with your fellow travelers and guides for a feast of traditional specialties at a restaurant steeped in local character. Perhaps enjoy a perfectly paired Nero d’Avola red wine with your meal. A stroll back to your hotel provides the perfect closure to your thrilling day.

Included Meals: Breakfast, Lunch, Dinner

5 miles, easy to moderate

After enjoying a leisurely breakfast, you bid Ragusa farewell and set off for one of the most beautiful spots in southeastern Sicily—the Oasi Nature Reserve at Vendicari, a marvelous ecosystem of coastal marshes with 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. Your footpath leads 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 takes in the entire reserve, from the splendid isle of Vendicari to Capo Passero in the distance. You may be enticed to take a swim! Your trail delivers you to a family-owned , where you enjoy a meal of regional specialties, including grilled vegetables, local Sicilian provola, pecorino and tuma cheeses, and freshly made pasta.

Afterward, travel to Syracuse, a UNESCO World Heritage site. When the island was ruled by Magna Graecia (ancient Greece), it rivalled Athens as the most powerful city in the empire. Here, a local expert leads you on a guided tour of the Parco Archeologico della Neapolis. Syracuse’s Archaeological Park is a treasure trove of important Greek and Roman monuments, including the spectacular 5th-century BCE Greek Theater. One of the finest of its kind, it still hosts Greek plays in the summer months. Nearby, the 2nd-century Anfiteatro Romano is the largest Roman amphitheater in Sicily and third-largest in Italy. Unlike the Greek Theater, the Roman Amphitheater bore witness to gruesome events such as gladiator fights and slave punishments.

Continue to modern-day Syracuse. The cultural and administrative capital of southeastern Sicily, the city is renowned for its extravagant Baroque architecture, historical ruins, gastronomic delights, beautiful landscapes, and stunning beaches. Your home for two nights is in Ortigia, the historical heart of Syracuse. 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. Ringed by exquisite Baroque buildings constructed after the 1693 earthquake, the plaza’s centerpiece is the Duomo (cathedral), a remarkable amalgam of evolving architectural styles that have shaped it over the centuries. The cathedral’s Baroque façade 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. All roads from this piazza lead to dinner, and as always suggestions for venues to accommodate your preferences are provided by your guides.

Included Meals: Breakfast, Lunch

4-7-mile options, moderate, 700-1,000-ft. elevation gain and loss

Start today on the hotel’s panoramic rooftop terrace with an elaborate breakfast of fruit, yogurt, fresh-pressed juices, omelets, cured meats and cheeses, and Sicilian pastries with pistachio cream. Then, 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, Pantalica 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. Your walking options range from 2 to 3 hours in length and lead through a dramatic river-carved landscape of limestone formations luxuriant in colorful, fragrant Mediterranean vegetation.

A short drive 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.

After lunch, travel back to Ortigia. Take time to relax and refresh before gathering this evening for a memorable farewell meal of fresh local seafood and crisp white wine to toast the week’s discoveries.

Included Meals: Breakfast, Lunch, Dinner

After savoring breakfast at your hotel, bid farewell to your tour guides and travel companions and enjoy a final day relaxing at your hotel or exploring Syracuse. The hotel has a private beach across the gulf that is open from June to September. Inquire with reception about boat transportation to and from.

Lunch and dinner are on your own today. We provide detailed city information on Syracuse to help you plan your exploration.

Included Meals: Breakfast

3 miles, easy to moderate

Your guides meet you in the lobby of the Grand Hotel Piazza Borsa, Via Cartari, 18, Palermo at 8:30 a.m. They will be wearing Country Walkers shirts. Please be dressed for walking.

Departing Palermo, an hour (to 75-minute) drive delivers you to the trailhead and the first of many magnificent archaeological sites, Segesta. Dating to 430 BCE and situated alone in a field amongst Mediterranean macchia (shrubbery) and wildflowers, it is one of Italy’s best-preserved ancient temples. It features a marvelous Doric temple. Founded by the Elymians, a mysterious ancient people, the city of Segesta was fought over for centuries before eventually being conquered by the Romans. Discover the area on foot, taking in the atmosphere of this spectacular setting 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 (or baglio) 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, enjoy an espresso (or macchiato) while you learn how to prepare typical almond pastries or cassata, another Sicilian specialty.

This afternoon you continue 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 (or by the famous salt flats), then gather for a welcome aperitivo followed by dinner, perhaps savoring cuscus (couscous) and fresh-caught fish (reflecting the city’s North African influences).

Included Meals: Lunch, Dinner

4-8 miles, moderate and 1 mile, easy

Departing Trapani, a 45-minute transfer delivers you to today’s walk in the Riserva Naturale di Monte Cofano, a towering limestone promontory jutting out between the turquoise Gulfs of Bonagia and Cofano. The reserve features well-maintained paths (your guides will review walk options prior to reaching the reserve), panoramic sea views, secluded bays, steep cliffs, and diverse flora and fauna. The landmark headland is also home to historic watchtowers, immense caves, and archaeological sites of prehistoric settlement. Finishing up the walk, a 10-minute drive brings you to lunch featuring western Sicilian cuisine in the neighboring town of Custonaci.

Afterward, 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.

A 90-minute journey south brings you to the countryside of Menfi and your home for the next two nights at a splendid 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.

Included Meals: Breakfast, Lunch, Dinner

3-5 miles, easy

After a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries and bread, and of course a cappuccino (or espresso), served 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 BCE, and hence the object of centuries of battles.

Following lunch, your guides may offer an easygoing hour-long optional walk above the hotel or a trail close to the seaside, or you may choose to enjoy a leisurely afternoon at the hotel to relax, and perhaps swim in the hotel’s outdoor swimming pool. This evening, you gather for another special dinner featuring the bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

2-4 miles, easy to moderate

After savoring breakfast at your hotel, drive southeast (approximately 60 minutes) to Riserva Naturale Orientata Torre Salsa, a nature reserve created in 1996 and managed by the World Wildlife Fund, it boasts a unique combination of hills, cliffs, sand dunes, fields and wetlands that are home to a variety of flora and fauna, including peregrine falcons, kestrels and horned owls as well as caretta caretta turtles. Enjoy a scenic walk (options along the park’s well-marked trails will be reviewed by your guides depending on the weather and fitness level of the group).

Afterward, continue to nearby Siculiana, a tiny village whose origins date back to the 10th century BCE, where you refuel over lunch of antipasti di mare or appetizers “from the sea” and other local specialties prior to continuing northeast for a two-hour drive to the outskirts of Caltagirone, where you find your next 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 into your room or relax by the outdoor pool, a feast of traditional dishes, perfectly paired with local Nero d’Avola red wine, is served in the warm, wood-beamed dining room.

Included Meals: Breakfast, Lunch, Dinner

1-2 miles, easy and 4 miles, moderate

After awakening in the peaceful countryside and eating breakfast, you set off (on a 30-minute drive) to the magnificent Villa Romana del Casale, considered the most important Roman archaeological site in Sicily. This Roman villa, or hunting lodge, is a UNESCO World Heritage site that was built around the 3rd and 4th centuries (AD). It is known for its extraordinary collection of mosaics in various stages of restoration. Walkways take you through some of its 40 rooms carpeted with 4,200 square yards of magnificent mosaics depicting vivid scenes from mythology, hunting and fishing, and scenes of everyday Roman life. Concluding your visit, you travel (90 minutes) to one of Sicily’s most fascinating nature reserves and archaeological sites, the Necropolis of Pantalica, stopping en route for lunch, comprised of dishes that are derived from locally sourced, seasonal ingredients reflecting the ancient traditions of the Anapo Valley.

Pantalica is a plateau rising between the canyons of the Anapo and Calcinara rivers, and 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 BCE. You walk through a dramatic river-carved landscape of limestone formations, luxuriant in colorful, fragrant Mediterranean vegetation.

Late afternoon, you continue to Syracuse. At one time this city rivaled Athens as the most powerful city 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, historical ruins, gastronomic delights, beautiful landscapes, and beaches. Your home for two nights is in Ortigia, the historical heart of Syracuse. Upon settling into your room, you 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. Ringed by exquisite baroque buildings constructed after the 1693 earthquake, the plaza’s 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 BCE temple of Athena; however, 26 of the temple’s Doric columns remain intact and are visible both inside and outside.

Included Meals: Breakfast, Lunch

5 miles, easy to moderate and 1 mile, easy

Start today with an elaborate breakfast of fruit, yogurt, fresh-pressed juices, omelets, cured meats and cheeses, and Sicilian pastries with pistachio cream enjoyed on the hotel’s panoramic rooftop terrace. Then, you depart for one of the most beautiful spots in southeastern Sicily—the Oasi Nature Reserve at Vendicari, a complex of coastal marshes with 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.

After lunch, travel by minibus to 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 of its kind, it still hosts Greek plays in the summer months. Nearby, is the 2nd-century Anfiteatro Romano, the largest Roman amphitheater in Sicily and third-largest in Italy. Unlike the Greek Theater, the Roman Amphitheater bore witness to gruesome events, such as gladiator fights and slave punishments. Late afternoon, you return to Ortigia, where you enjoy another relaxing evening on your own.

Included Meals: Breakfast, Lunch

Milo to Zafferana Etnea; 5 miles, moderate to challenging, 500-ft. elevation gain and 1,900-ft. elevation loss

Following a delicious breakfast, you depart Syracuse for Mt. Etna, whose majestic cone is the highest mountain in Sicily and one of the largest active volcanoes in Europe. Over 11,000 feet high and occupying an area larger than metropolitan New York, the mountain presents a fascinating alpine environment with a combination of nature and the uncontrollable essence of fire. Walk options today are again weather- and volcano-dependent and may include a trail along the Sentiero delle Ginestre (the Broom Route) from the village of Milo to Zafferana Etnea, through an area of chestnut forest, old shepherd settlements, the famous giant broom trees, and even a live oak that is over 700 years old. A sustained descent brings you to Zafferana Etnea, an important crossroads in the Roman era along the inland route that connected Catania with Taormina.

Almost constant activity from this volcano has gifted its slopes with fertile soils for agriculture, orchards, and vineyards, and midday finds you at one of the many emerging wineries on Etna’s slopes, where you’re treated to a light lunch and tasting. The location affords excellent views of the vineyards on one side and the volcano on the other.

Following lunch, continue to a family-owned country boutique hotel set amid grapevines and citrus groves. Settle in, and enjoy a leisurely afternoon at the hotel offers time to pack, relax, and perhaps swim in the hotel’s outdoor swimming pool. This evening, you gather for a special dinner paired with a glass (or two!) of wine from nearby vineyards—perfect for toasting your discoveries of enchanting Sicily.

Included Meals: Breakfast, Lunch, Dinner

After savoring breakfast at your hotel, bid farewell to your tour guides and travel companions, and make flight or rail connections for onward travels. The hotel can assist with any transportation required to Catania or beyond. (The hotel check out time is 11:00 a.m.).

Included Meals: Breakfast

3-4 miles, easy to moderate, 500-ft. elevation gain and loss

Your guides meet you in the lobby of Hotel Monte Tauro in Taormina at 9:00 a.m. They will be wearing Country Walkers shirts. Please be dressed for hiking (with appropriate footwear and backpack).

Departing Taormina, a short drive delivers you to your first trailhead on Mt. Etna’s quiet, picturesque northern slopes. whose majestic cone is the highest mountain in Sicily and one of the largest active volcanoes in Europe. Over 11,000 feet high and occupying an area larger than metropolitan New York, the mountain presents a fascinating alpine environment that combines the beauty of nature and the uncontrollable essence of fire. Hiking options on the volcano’s quiet, picturesque northern slopes today are weather- and volcano-dependent and may include an adventurous climb to the recently formed craters of Monte Nero and the Bottoniera, or through Linguaglossa pine forest, crossing a corridor of lava flow. (Maximum altitude for the walk is approximately 7,000 feet.) Weather permitting, you are treated to a Sicilian-style picnic lunch of crusty bread, sun-dried tomatoes, fruit, cured meats, and local cheeses enjoyed trailside or at a rifugio (alpine hut).

This afternoon you travel to your nearby home-away-from-home for the next two nights: a family-owned country boutique hotel set amid grapevines and citrus groves. Settle in, then gather poolside for a welcome aperitivo, followed by a delicious dinner in the hotel’s Michelin-starred restaurant featuring elegant, refined Sicilian fare, paired with a glass (or two) of wine from the nearby fertile slopes.

Included Meals: Lunch, Dinner

5 miles, moderate to challenging, 500-ft. elevation gain and 1,900-ft. elevation loss

Following a delicious breakfast, begin your day with a drive to Mt. Etna’s picturesque eastern slopes. Hiking options today are again weather- and volcano-dependent and may include a trail along the Sentiero delle Ginestre (or the Broom Route) from the village of Milo to Zafferana Etnea, trekking through an area of chestnut forest and passing old shepherd settlements, the famous giant broom trees, and even a live oak that is over 700 years old. A sustained descent brings you to Zafferana Etnea, an important Roman-era crossroads that connected Catania with Taormina.

Almost constant activity from this volcano has blessed its slopes with fertile soils for agriculture, orchards, and vineyards. Midday, you arrive at one of the many emerging wineries on Etna’s slopes, where you’re treated to a light lunch and tasting. Its location affords excellent views of the vineyards on one side and the volcano on the other. You return to your country house hotel with time to relax and refresh prior to stepping out for another dinner that reflects the bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

3-4 mile options, easy to moderate, 500-ft. elevation gain and loss

Awaken at your tranquil resort to a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries and bread, and of course a cappuccino (or espresso). Then travel about 60 minutes to your trailhead outside Militello in the Val di Catania. Along with seven other nearby towns, Militello was gorgeously rebuilt in stunning Late Baroque style after a devastating 1693 earthquake, earning much of the Val di Noto status as a UNESCO World Heritage site for its architectural splendor. Today, Militello is celebrated for its fragrant orange groves, traditional mulled wine, and prickly pear cakes. From here, you set out on a scenic trail to the spectacular Cascate dell’Oxena, or Oxena River Waterfalls. Your pathway follows the canyon-like course of the river along basalt rocks formed by ancient volcanic eruptions. Luxuriant stands of olivastri, elms, ash trees, oaks, prickly pears, carob trees, tamarisks and oleanders mark your progress and you’ll have opportunities to take a refreshing dip in the river’s natural pools.

Refuel over a simple lunch of Sicilian specialties, like arancine—or seasoned rice balls with meat, fish, or eggplant, mushrooms and spinach—before continuing to your next destination. Following lunch, travel approximately to the valley of Noto, where the town of Ragusa is perched on a limestone hill. Ragusa Ibla, the Old Town, shared in the remarkable Baroque building boom at the turn of the 18th century, and you’ll have time to explore it up close tomorrow. Your accommodations in a former palace put you close to the spectacular Old Town. Providing an elegant mix of modernity and tradition, the hotel was skillfully refurbished to preserve its historic character while melding harmoniously with modern design. Dinner is on your own this evening; your guides will provide recommendations of the area’s best restaurants.

Included Meals: Breakfast, Dinner

3-5 miles, easy to moderate (with challenging sections), 600-900-ft. maximum elevation gain and loss, and 1-2 miles, easy

After savoring a breakfast of traditional local products in the fresh, clean air of your hotel’s elegant patio, head out for a hike along scenic pathways along the Cava della Misericordia, the Cave of Mercy. Your trail through pine, poplar, and oak forest leads you along an ancient quarry where evidence of human settlement has been left behind. Pass the Church of St. Elia, dedicated to the saint who many believed brought droughts to an end. Pause at an old Ibleo Byzantine cemetery, where some 3,000 souls were laid to rest. See the ruins of old mills and houses. And, finally, arrive at the Hermitage of Our Lady of Mercy, an ancient Benedictine Monastery built into the rocky landscape.

After, head to a nearby agriturismo (an agricultural farm estate), where a lunch of local specialties awaits. Enjoy farm-fresh ingredients and home-prepared specialties like Ragusan scacce, thin sheets of dough filled with spinach, ricotta, tomato and onion or eggplant and parsley.

Continue to Ragusa Ibla, where there’ll be time to explore this jewel with your guides. Stroll among its magnificent architecture—part of the final blossoming of European Baroque. Pause for a visit to an artisan studio to learn about the tradition of the Carretti Siciliani, the famed Sicilian horse carts adorned with elaborate paintings that depicted the local ideals of chivalry, faith, honor, and justice.

Continue exploring on your own, or maybe return to the hotel and treat yourself to time in the wellness center. Indulge in a massage, Turkish bath with aromatic oils, indoor salt water pool, and more. You may also enjoy the garden and outdoor pool at the nearby sister property. Reunite later with your fellow travelers and guides for a feast of traditional specialties at a restaurant steeped in local character. Perhaps enjoy a perfectly paired Nero d’Avola red wine with your meal. A stroll back to your hotel provides the perfect closure to your thrilling day.

Included Meals: Breakfast, Lunch, Dinner

5 miles, easy to moderate

After enjoying a leisurely breakfast, you bid Ragusa farewell and set off for one of the most beautiful spots in southeastern Sicily—the Oasi Nature Reserve at Vendicari, a marvelous ecosystem of coastal marshes with 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. Your footpath leads 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 takes in the entire reserve, from the splendid isle of Vendicari to Capo Passero in the distance. You may be enticed to take a swim! Your trail delivers you to a family-owned , where you enjoy a meal of regional specialties, including grilled vegetables, local Sicilian provola, pecorino and tuma cheeses, and freshly made pasta.

Afterward, travel to Syracuse, a UNESCO World Heritage site. When the island was ruled by Magna Graecia (ancient Greece), it rivalled Athens as the most powerful city in the empire. Here, a local expert leads you on a guided tour of the Parco Archeologico della Neapolis. Syracuse’s Archaeological Park is a treasure trove of important Greek and Roman monuments, including the spectacular 5th-century BCE Greek Theater. One of the finest of its kind, it still hosts Greek plays in the summer months. Nearby, the 2nd-century Anfiteatro Romano is the largest Roman amphitheater in Sicily and third-largest in Italy. Unlike the Greek Theater, the Roman Amphitheater bore witness to gruesome events such as gladiator fights and slave punishments.

Continue to modern-day Syracuse. The cultural and administrative capital of southeastern Sicily, the city is renowned for its extravagant Baroque architecture, historical ruins, gastronomic delights, beautiful landscapes, and stunning beaches. Your home for two nights is in Ortigia, the historical heart of Syracuse. 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. Ringed by exquisite Baroque buildings constructed after the 1693 earthquake, the plaza’s centerpiece is the Duomo (cathedral), a remarkable amalgam of evolving architectural styles that have shaped it over the centuries. The cathedral’s Baroque façade 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. All roads from this piazza lead to dinner, and as always suggestions for venues to accommodate your preferences are provided by your guides.

Included Meals: Breakfast, Lunch

4-7-mile options, moderate, 700-1,000-ft. elevation gain and loss

Start today on the hotel’s panoramic rooftop terrace with an elaborate breakfast of fruit, yogurt, fresh-pressed juices, omelets, cured meats and cheeses, and Sicilian pastries with pistachio cream. Then, 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, Pantalica 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. Your walking options range from 2 to 3 hours in length and lead through a dramatic river-carved landscape of limestone formations luxuriant in colorful, fragrant Mediterranean vegetation.

A short drive 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.

After lunch, travel back to Ortigia. Take time to relax and refresh before gathering this evening for a memorable farewell meal of fresh local seafood and crisp white wine to toast the week’s discoveries.

Included Meals: Breakfast, Lunch, Dinner

Milo to Zafferana Etnea; 5 miles, moderate to challenging, 500-ft. elevation gain and 1,900-ft. elevation loss

After savoring breakfast at your hotel, bid farewell to your tour guides and travel companions, and make flight or rail connections for onward travels. The hotel can assist with any transportation required to Catania or beyond. (Check out time is 11:00 a.m.).

Included Meals: Breakfast