Italy: Sicily

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day right by having a Country Walkers representative greet you at Catania’s Fontanarossa Airport. Complimentary transportation will be provided to your Taormina hotel. From here, you are perfectly positioned to explore this vibrant city at your leisure.

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

Meet your fellow travelers and your Country Walkers leaders—easily identified by their Country Walkers shirts—in the lobby of Hotel Monte Tauro in Taormina at 8:30 a.m. with your luggage. Please be dressed for hiking—appropriate attire, sturdy footwear, and a daypack (to carry rain gear and a water bottle) are required.

Departing Taormina, a short drive brings you to your first trailhead in the foothills of Mt. Etna’s quiet, picturesque northern slopes. Etna’s majestic cone—the highest peak in Sicily and one of Europe’s largest active volcanoes—rises over 11,000 feet and spans an area greater than metropolitan New York. Its dramatic alpine landscapes reflect a striking mix of serene natural beauty and powerful geologic activity.

Hiking routes on or near the volcano’s slopes today are weather- and volcano-dependent, but may include an easy trail beginning in Linguaglossa, winding through hazelnut and olive groves and along part of a converted rail trail to the village of Castiglione di Sicilia. Known as “the quastallum” (or “the castle”) by a renowned Arab geographer, this scenic town sits on a hill between the Alcantara Valley and Etna Park, offering lovely views among fruit trees, vineyards, and ancient lava flows.

Upon arrival in Castiglione, you’ll meet your dedicated driver and transfer across the valley to the medieval village of Motta Camastra. Here, you are welcomed with a Sicilian-style lunch of crusty bread, olives, seasonal fruit, cured meats, pasta, and cheeses—served under a vine-covered pergola.

This memorable meal is part of a unique social dining project called Le Mamme del Borgo (“The Mothers of the Village”), which blends traditional Sicilian cuisine with moments of shared joy, local ingredients, and authentic connection to the community. By dining here, you are helping support this meaningful initiative and enjoying a deeper experience of local culture. Guests are welcome to step into the simple kitchen for a closer look at how these time-honored dishes are prepared.

After lunch, enjoy a guided stroll through Motta Camastra’s atmospheric streets—made famous as the fictional town of Corleone in The Godfather. Keep an eye out for colorful local characters and enjoy the village’s warm hospitality.

Later this afternoon, travel to your home-away-from-home for the next two nights: a family-owned boutique country hotel nestled among vineyards and citrus groves. Settle in, then gather poolside for a welcome aperitivo, followed by a delicious dinner at the hotel’s Michelin-starred restaurant. Savor innovative Sicilian fare paired with wines from the fertile volcanic slopes nearby.

Included Meals: Breakfast, Lunch, Dinner

2-5 miles, moderate to challenging, 400-1,000 ft. maximum elevation gain and loss

Following a delicious breakfast, begin your day with a drive to Mt. Etna’s picturesque southern slopes. Hiking options today are again weather- and volcano-dependent and may include trails above the town of Nicolosi—gateway to many excursions on the volcano and home to the Museum of Etna, which highlights both the geologic and cultural history of this remarkable site.

Your featured trail begins at an elevation of just over 4,000 feet and offers flexibility in both distance and elevation, accommodating a variety of hiking preferences. Those seeking a challenge can hike around Monte Gemmellaro—formed during an 1886 eruption—on a full 5-mile circuit with approximately 1,000 feet of elevation gain and loss. A shorter option around Monte Grosso spans roughly 2 miles, with about 400 feet of elevation gain and loss. For an even lighter experience, you may simply walk about a mile out and back along the same well-established trail, enjoying views on a clear day.

Regardless of the route you choose, weather permitting, as you approach Monte Grosso, you’ll be rewarded with sweeping views over the Gulf of Catania and across dramatic volcanic terrain—including hornitos, pyroclastic cones, lava flows, and flow channels. The trail is named in honor of Carlo Gemmellaro, a 19th-century professor of natural history, geology, and mineralogy at the University of Catania, whose work helped establish a globally respected geological school. The route features mixed terrain, from wide to narrow paths of lava gravel, and passes through vegetation such as pine and broom.

Almost constant volcanic activity has blessed Etna’s slopes with rich, fertile soils, ideal for agriculture, orchards, and vineyards. Around midday, arrive at one of the many emerging wineries on Etna’s flanks, where you’ll enjoy a light lunch and wine tasting. The location offers striking views—vineyards on one side, the volcano on the other.

Return to your country house hotel with time to relax and refresh before heading out for another dinner that celebrates the rich bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

3-4 mile options, easy to moderate (with some challenging terrain), 350-ft. elevation gain and 1,000-ft. elevation loss

Awaken at your tranquil resort to a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries, and bread—accompanied, of course, by a cappuccino or espresso. Then travel about 60–75 minutes to your trailhead in Ramacca, just west of the Plain of Catania. This area is renowned for both its archaeological and agricultural significance. Your pathway leads through the hilly landscape of the Erei Mountains, where gypsum rock appears in striking formations of coarse crystals, such as selenite (also known as moonstone). Along the way, luxuriant stands of olivastri, oaks, prickly pears, carob, citrus orchards, and oleanders mark your progress.

The trail culminates beneath the imposing Serravalle Castle, a medieval gem that has belonged to the Grimaldi family since the early 1500s.

You are warmly welcomed at a splendid estate owned by your local hosts, Gerardo and Mariarosa, where you refuel with a lunch of Sicilian specialties. Afterward, explore their expansive citrus groves and learn about the innovative techniques they’ve adopted to manage the growing challenges of climate change in the region.

Later, travel approximately 75 minutes to the valley of Noto—much of which is a UNESCO World Heritage site, recognized for its extraordinary late Baroque architecture rebuilt after the devastating 1693 earthquake. Arrive in the late afternoon to the hilltop town of Ragusa. Ragusa Ibla, the Old Town, was a key part of this Baroque renaissance, and you’ll have time to explore its winding streets up close tomorrow.

Your accommodations—a former palace—place you near the heart of the spectacular Old Town. The hotel blends modern comfort with historical charm, thoughtfully renovated to preserve its heritage while incorporating stylish contemporary design. After settling in and refreshing, rejoin your fellow travelers and leaders for a festive dinner featuring traditional regional fare at a restaurant steeped in local character. A leisurely stroll back to the hotel is the perfect close to your day.

Included Meals: Breakfast, Lunch, Dinner

3-5 miles, easy to moderate (with challenging sections), 350-ft. maximum elevation gain and 1,100-1,250-ft elevation loss, and 1-2 miles, easy

After savoring a breakfast of traditional local products, set out for a hike along the scenic pathways of the Cava della Misericordia, or Cave of Mercy. Your leaders will share details about the walk options available in the area. The trail winds through forests of pine, poplar, and oak, following an ancient quarry that bears traces of early human settlement. As you descend, pass the Benedictine convent and the ruins of old mills and stone houses. In spring, the route bursts with wildflowers—orchids, poppies, and wild asparagus creating a colorful display.

Continue on to Ragusa Ibla and explore this architectural gem with your leaders. Wander its elegant streets, home to some of the finest examples of late European Baroque design. Take time to enjoy lunch on your own at one of the many welcoming trattorias.

In the afternoon, reunite with your fellow travelers for a visit to an artisan studio, where you’ll learn about the tradition of the Carretti Siciliani—the famed Sicilian horse carts, intricately painted to depict themes of chivalry, faith, honor, and justice.

The rest of the day is yours to enjoy at your leisure. Continue exploring the charming streets of Ragusa Ibla, or return to the hotel to unwind. At De Stefano Palace, an elegant spa and wellness center invite you to relax and rejuvenate (treatments at your own expense). The facility features a Turkish bath, a saltwater heated pool, an emotional shower, a relaxation area with herbal teas, and a menu of treatments designed for both body and face.

Dinner is on your own this evening, with recommendations from your leaders to guide your culinary exploration.

Included Meals: Breakfast

5 miles, easy to moderate

After enjoying a leisurely breakfast, bid farewell to Ragusa and set off for one of southeastern Sicily’s most beautiful natural spots—the Oasi Nature Reserve at Vendicari. This marvelous coastal ecosystem, with its serene sandy beach and protected marshes, is home to a wide variety of migratory birds. Depending on the season and time of day, you may spot 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 this vantage point, you’ll enjoy sweeping views of the entire reserve—from the splendid Isle of Vendicari to Capo Passero on the horizon. You may even be tempted to take a swim!

Your trail concludes at a family-owned agriturismo, where you’ll enjoy a lunch of regional specialties—grilled vegetables, local Sicilian provola, pecorino, and tuma cheeses, and freshly made pasta.

After lunch, continue to Syracuse, a UNESCO World Heritage site. During the era of Magna Graecia, this city rivaled Athens as the most powerful in the ancient Greek world. Here, a local expert leads you on a guided tour of the Parco Archeologico della Neapolis—a treasure trove of Greek and Roman monuments. Highlights include the spectacular 5th-century BCE Greek Theater, still used for summer performances, and the nearby 2nd-century Roman Amphitheater (Anfiteatro Romano), the largest in Sicily and the third-largest in Italy. Unlike the Greek Theater, which celebrated art and drama, the Roman Amphitheater hosted brutal gladiator battles and slave punishments.

From here, continue to modern-day Syracuse, the cultural and administrative capital of southeastern Sicily. Known for its extravagant Baroque architecture, archaeological heritage, culinary delights, and coastal beauty, the city offers much to explore. Your home for the next two nights is on the island of Ortigia, the historical heart of Syracuse.

After settling in, enjoy an evening of independent exploration and dining. You might stroll through the Piazza del Duomo, widely regarded as one of Italy’s most beautiful squares. Surrounded by elegant Baroque buildings rebuilt after the 1693 earthquake, the plaza’s centerpiece is the Duomo (cathedral)—a striking fusion of architectural styles. Beneath its Baroque façade lie the remains of the 5th-century BCE Temple of Athena, including 26 preserved Doric columns visible both inside and out.

All roads from this piazza lead to dinner, and—as always—your leaders are happy to provide personalized recommendations to suit your preferences.

Included Meals: Breakfast, Lunch

1.5 miles, easy, 100-ft elevation gain and 300-ft elevation loss, or 2 miles, 450-ft elevation gain and 300-ft elevation loss, or 4 miles, moderate, 800-ft elevation gain and 700-ft. elevation loss

Start your day 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 filled with pistachio cream. Then, depart for one of Sicily’s most fascinating natural and archaeological treasures: the Necropolis of Pantalica.

Perched on a plateau between the canyons of the Anapo and Calcinara rivers, Pantalica was inhabited from prehistoric times through the Middle Ages. Its steep rock walls are carved with more than 5,000 tombs, dating as far back as the second millennium BCE—making it the largest burial complex of its kind in Sicily. Your walk options today range from one to three hours and lead through a dramatic, river-carved landscape of limestone cliffs, rich with colorful and fragrant Mediterranean vegetation.

Lunch is on your own in the quaint hilltop village of Ferla. Choose from local antipasti and pasta dishes or enjoy a simple panino and gelato on the terrace of a café or restaurant across from the town’s beautiful church.

After lunch, return to Ortigia and take time to relax and refresh. This evening, gather with your fellow travelers for a memorable farewell dinner featuring fresh local seafood and crisp white wine—a perfect toast to the week’s discoveries.

Included Meals: Breakfast, Dinner

After savoring breakfast at your hotel, bid farewell to your leaders and travel companions, and enjoy a final day at your leisure—whether relaxing at the hotel or setting out to further explore the cultural richness of Syracuse. From June through September, the hotel offers access to a private beach across the gulf; inquire at reception about complimentary boat transportation to and from this peaceful retreat.

Lunch and dinner are on your own today. To help you make the most of your time, we provide detailed city information with recommendations for discovering Syracuse’s historic sites and culinary highlights.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation will be provided to Catania’s Fontanarossa Airport according to your departure time.

Included Meals: Breakfast

Your vacation is about to begin! Spend your first night aloft and arrive ready for an unforgettable trip.

Start off your first day right by having a Country Walkers representative greet you at Catania’s Fontanarossa Airport. Complimentary transportation will be provided to your Taormina hotel. From here, you are perfectly positioned to explore this vibrant city at your leisure.

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

Meet your fellow travelers and your Country Walkers leaders—easily identified by their Country Walkers shirts—in the lobby of Hotel Monte Tauro in Taormina at 8:30 a.m. with your luggage. Please be dressed for hiking—appropriate attire, sturdy footwear, and a daypack (to carry rain gear and a water bottle) are required.

Departing Taormina, a short drive brings you to your first trailhead in the foothills of Mt. Etna’s quiet, picturesque northern slopes. Etna’s majestic cone—the highest peak in Sicily and one of Europe’s largest active volcanoes—rises over 11,000 feet and spans an area greater than metropolitan New York. Its dramatic alpine landscapes reflect a striking mix of serene natural beauty and powerful geologic activity.

Hiking routes on or near the volcano’s slopes today are weather- and volcano-dependent, but may include an easy trail beginning in Linguaglossa, winding through hazelnut and olive groves and along part of a converted rail trail to the village of Castiglione di Sicilia. Known as “the quastallum” (or “the castle”) by a renowned Arab geographer, this scenic town sits on a hill between the Alcantara Valley and Etna Park, offering lovely views among fruit trees, vineyards, and ancient lava flows.

Upon arrival in Castiglione, you’ll meet your dedicated driver and transfer across the valley to the medieval village of Motta Camastra. Here, you are welcomed with a Sicilian-style lunch of crusty bread, olives, seasonal fruit, cured meats, pasta, and cheeses—served under a vine-covered pergola.

This memorable meal is part of a unique social dining project called Le Mamme del Borgo (“The Mothers of the Village”), which blends traditional Sicilian cuisine with moments of shared joy, local ingredients, and authentic connection to the community. By dining here, you are helping support this meaningful initiative and enjoying a deeper experience of local culture. Guests are welcome to step into the simple kitchen for a closer look at how these time-honored dishes are prepared.

After lunch, enjoy a guided stroll through Motta Camastra’s atmospheric streets—made famous as the fictional town of Corleone in The Godfather. Keep an eye out for colorful local characters and enjoy the village’s warm hospitality.

Later this afternoon, travel to your home-away-from-home for the next two nights: a family-owned boutique country hotel nestled among vineyards and citrus groves. Settle in, then gather poolside for a welcome aperitivo, followed by a delicious dinner at the hotel’s Michelin-starred restaurant. Savor innovative Sicilian fare paired with wines from the fertile volcanic slopes nearby.

Included Meals: Breakfast, Lunch, Dinner

2-5 miles, moderate to challenging, 400-1,000 ft. maximum elevation gain and loss

Following a delicious breakfast, begin your day with a drive to Mt. Etna’s picturesque southern slopes. Hiking options today are again weather- and volcano-dependent and may include trails above the town of Nicolosi—gateway to many excursions on the volcano and home to the Museum of Etna, which highlights both the geologic and cultural history of this remarkable site.

Your featured trail begins at an elevation of just over 4,000 feet and offers flexibility in both distance and elevation, accommodating a variety of hiking preferences. Those seeking a challenge can hike around Monte Gemmellaro—formed during an 1886 eruption—on a full 5-mile circuit with approximately 1,000 feet of elevation gain and loss. A shorter option around Monte Grosso spans roughly 2 miles, with about 400 feet of elevation gain and loss. For an even lighter experience, you may simply walk about a mile out and back along the same well-established trail, enjoying views on a clear day.

Regardless of the route you choose, weather permitting, as you approach Monte Grosso, you’ll be rewarded with sweeping views over the Gulf of Catania and across dramatic volcanic terrain—including hornitos, pyroclastic cones, lava flows, and flow channels. The trail is named in honor of Carlo Gemmellaro, a 19th-century professor of natural history, geology, and mineralogy at the University of Catania, whose work helped establish a globally respected geological school. The route features mixed terrain, from wide to narrow paths of lava gravel, and passes through vegetation such as pine and broom.

Almost constant volcanic activity has blessed Etna’s slopes with rich, fertile soils, ideal for agriculture, orchards, and vineyards. Around midday, arrive at one of the many emerging wineries on Etna’s flanks, where you’ll enjoy a light lunch and wine tasting. The location offers striking views—vineyards on one side, the volcano on the other.

Return to your country house hotel with time to relax and refresh before heading out for another dinner that celebrates the rich bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

3-4 mile options, easy to moderate (with some challenging terrain), 350-ft. elevation gain and 1,000-ft. elevation loss

Awaken at your tranquil resort to a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries, and bread—accompanied, of course, by a cappuccino or espresso. Then travel about 60–75 minutes to your trailhead in Ramacca, just west of the Plain of Catania. This area is renowned for both its archaeological and agricultural significance. Your pathway leads through the hilly landscape of the Erei Mountains, where gypsum rock appears in striking formations of coarse crystals, such as selenite (also known as moonstone). Along the way, luxuriant stands of olivastri, oaks, prickly pears, carob, citrus orchards, and oleanders mark your progress.

The trail culminates beneath the imposing Serravalle Castle, a medieval gem that has belonged to the Grimaldi family since the early 1500s.

You are warmly welcomed at a splendid estate owned by your local hosts, Gerardo and Mariarosa, where you refuel with a lunch of Sicilian specialties. Afterward, explore their expansive citrus groves and learn about the innovative techniques they’ve adopted to manage the growing challenges of climate change in the region.

Later, travel approximately 75 minutes to the valley of Noto—much of which is a UNESCO World Heritage site, recognized for its extraordinary late Baroque architecture rebuilt after the devastating 1693 earthquake. Arrive in the late afternoon to the hilltop town of Ragusa. Ragusa Ibla, the Old Town, was a key part of this Baroque renaissance, and you’ll have time to explore its winding streets up close tomorrow.

Your accommodations—a former palace—place you near the heart of the spectacular Old Town. The hotel blends modern comfort with historical charm, thoughtfully renovated to preserve its heritage while incorporating stylish contemporary design. After settling in and refreshing, rejoin your fellow travelers and leaders for a festive dinner featuring traditional regional fare at a restaurant steeped in local character. A leisurely stroll back to the hotel is the perfect close to your day.

Included Meals: Breakfast, Lunch, Dinner

3-5 miles, easy to moderate (with challenging sections), 350-ft. maximum elevation gain and 1,100-1,250-ft elevation loss, and 1-2 miles, easy

After savoring a breakfast of traditional local products, set out for a hike along the scenic pathways of the Cava della Misericordia, or Cave of Mercy. Your leaders will share details about the walk options available in the area. The trail winds through forests of pine, poplar, and oak, following an ancient quarry that bears traces of early human settlement. As you descend, pass the Benedictine convent and the ruins of old mills and stone houses. In spring, the route bursts with wildflowers—orchids, poppies, and wild asparagus creating a colorful display.

Continue on to Ragusa Ibla and explore this architectural gem with your leaders. Wander its elegant streets, home to some of the finest examples of late European Baroque design. Take time to enjoy lunch on your own at one of the many welcoming trattorias.

In the afternoon, reunite with your fellow travelers for a visit to an artisan studio, where you’ll learn about the tradition of the Carretti Siciliani—the famed Sicilian horse carts, intricately painted to depict themes of chivalry, faith, honor, and justice.

The rest of the day is yours to enjoy at your leisure. Continue exploring the charming streets of Ragusa Ibla, or return to the hotel to unwind. At De Stefano Palace, an elegant spa and wellness center invite you to relax and rejuvenate (treatments at your own expense). The facility features a Turkish bath, a saltwater heated pool, an emotional shower, a relaxation area with herbal teas, and a menu of treatments designed for both body and face.

Dinner is on your own this evening, with recommendations from your leaders to guide your culinary exploration.

Included Meals: Breakfast

5 miles, easy to moderate

After enjoying a leisurely breakfast, bid farewell to Ragusa and set off for one of southeastern Sicily’s most beautiful natural spots—the Oasi Nature Reserve at Vendicari. This marvelous coastal ecosystem, with its serene sandy beach and protected marshes, is home to a wide variety of migratory birds. Depending on the season and time of day, you may spot 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 this vantage point, you’ll enjoy sweeping views of the entire reserve—from the splendid Isle of Vendicari to Capo Passero on the horizon. You may even be tempted to take a swim!

Your trail concludes at a family-owned agriturismo, where you’ll enjoy a lunch of regional specialties—grilled vegetables, local Sicilian provola, pecorino, and tuma cheeses, and freshly made pasta.

After lunch, continue to Syracuse, a UNESCO World Heritage site. During the era of Magna Graecia, this city rivaled Athens as the most powerful in the ancient Greek world. Here, a local expert leads you on a guided tour of the Parco Archeologico della Neapolis—a treasure trove of Greek and Roman monuments. Highlights include the spectacular 5th-century BCE Greek Theater, still used for summer performances, and the nearby 2nd-century Roman Amphitheater (Anfiteatro Romano), the largest in Sicily and the third-largest in Italy. Unlike the Greek Theater, which celebrated art and drama, the Roman Amphitheater hosted brutal gladiator battles and slave punishments.

From here, continue to modern-day Syracuse, the cultural and administrative capital of southeastern Sicily. Known for its extravagant Baroque architecture, archaeological heritage, culinary delights, and coastal beauty, the city offers much to explore. Your home for the next two nights is on the island of Ortigia, the historical heart of Syracuse.

After settling in, enjoy an evening of independent exploration and dining. You might stroll through the Piazza del Duomo, widely regarded as one of Italy’s most beautiful squares. Surrounded by elegant Baroque buildings rebuilt after the 1693 earthquake, the plaza’s centerpiece is the Duomo (cathedral)—a striking fusion of architectural styles. Beneath its Baroque façade lie the remains of the 5th-century BCE Temple of Athena, including 26 preserved Doric columns visible both inside and out.

All roads from this piazza lead to dinner, and—as always—your leaders are happy to provide personalized recommendations to suit your preferences.

Included Meals: Breakfast, Lunch

1.5 miles, easy, 100-ft elevation gain and 300-ft elevation loss, or 2 miles, 450-ft elevation gain and 300-ft elevation loss, or 4 miles, moderate, 800-ft elevation gain and 700-ft. elevation loss

Start your day 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 filled with pistachio cream. Then, depart for one of Sicily’s most fascinating natural and archaeological treasures: the Necropolis of Pantalica.

Perched on a plateau between the canyons of the Anapo and Calcinara rivers, Pantalica was inhabited from prehistoric times through the Middle Ages. Its steep rock walls are carved with more than 5,000 tombs, dating as far back as the second millennium BCE—making it the largest burial complex of its kind in Sicily. Your walk options today range from one to three hours and lead through a dramatic, river-carved landscape of limestone cliffs, rich with colorful and fragrant Mediterranean vegetation.

Lunch is on your own in the quaint hilltop village of Ferla. Choose from local antipasti and pasta dishes or enjoy a simple panino and gelato on the terrace of a café or restaurant across from the town’s beautiful church.

After lunch, return to Ortigia and take time to relax and refresh. This evening, gather with your fellow travelers for a memorable farewell dinner featuring fresh local seafood and crisp white wine—a perfect toast to the week’s discoveries.

Included Meals: Breakfast, Dinner

After savoring breakfast at your hotel, bid farewell to your leaders and travel companions, and enjoy a final day at your leisure—whether relaxing at the hotel or setting out to further explore the cultural richness of Syracuse. From June through September, the hotel offers access to a private beach across the gulf; inquire at reception about complimentary boat transportation to and from this peaceful retreat.

Lunch and dinner are on your own today. To help you make the most of your time, we provide detailed city information with recommendations for discovering Syracuse’s historic sites and culinary highlights.

Included Meals: Breakfast

After an included breakfast this morning, complimentary transportation will be provided to Catania’s Fontanarossa Airport according to your departure time.

Included Meals: Breakfast

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

Meet your fellow travelers and your Country Walkers leaders in the lobby of our pre-tour hotel, Hotel Monte Tauro in Taormina, at 8:30 a.m. with your luggage. Please be dressed for hiking—appropriate attire, sturdy footwear, and a daypack (to carry rain gear and a water bottle) are required.

Departing Taormina, a short drive brings you to your first trailhead in the foothills of Mt. Etna’s quiet, picturesque northern slopes. Etna’s majestic cone—the highest peak in Sicily and one of Europe’s largest active volcanoes—rises over 11,000 feet and spans an area greater than metropolitan New York. Its dramatic alpine landscapes reflect a striking mix of serene natural beauty and powerful geologic activity.

Hiking routes on or near the volcano’s slopes today are weather- and volcano-dependent, but may include an easy trail beginning in Linguaglossa, winding through hazelnut and olive groves and along part of a converted rail trail to the village of Castiglione di Sicilia. Known as “the quastallum” (or “the castle”) by a renowned Arab geographer, this scenic town sits on a hill between the Alcantara Valley and Etna Park, offering lovely views among fruit trees, vineyards, and ancient lava flows.

Upon arrival in Castiglione, you’ll meet your dedicated driver and transfer across the valley to the medieval village of Motta Camastra. Here, you are welcomed with a Sicilian-style lunch of crusty bread, olives, seasonal fruit, cured meats, pasta, and cheeses—served under a vine-covered pergola.

This memorable meal is part of a unique social dining project called Le Mamme del Borgo (“The Mothers of the Village”), which blends traditional Sicilian cuisine with moments of shared joy, local ingredients, and authentic connection to the community. By dining here, you are helping support this meaningful initiative and enjoying a deeper experience of local culture. Guests are welcome to step into the simple kitchen for a closer look at how these time-honored dishes are prepared.

After lunch, enjoy a guided stroll through Motta Camastra’s atmospheric streets—made famous as the fictional town of Corleone in The Godfather. Keep an eye out for colorful local characters and enjoy the village’s warm hospitality.

Later this afternoon, travel to your home-away-from-home for the next two nights: a family-owned boutique country hotel nestled among vineyards and citrus groves. Settle in, then gather poolside for a welcome aperitivo, followed by a delicious dinner at the hotel’s Michelin-starred restaurant. Savor innovative Sicilian fare paired with wines from the fertile volcanic slopes nearby.

Included Meals: Lunch, Dinner

2-5 miles, moderate to challenging, 400-1,000 ft. maximum elevation gain and loss

Following a delicious breakfast, begin your day with a drive to Mt. Etna’s picturesque southern slopes. Hiking options today are again weather- and volcano-dependent and may include trails above the town of Nicolosi—gateway to many excursions on the volcano and home to the Museum of Etna, which highlights both the geologic and cultural history of this remarkable site.

Your featured trail begins at an elevation of just over 4,000 feet and offers flexibility in both distance and elevation, accommodating a variety of hiking preferences. Those seeking a challenge can hike around Monte Gemmellaro—formed during an 1886 eruption—on a full 5-mile circuit with approximately 1,000 feet of elevation gain and loss. A shorter option around Monte Grosso spans roughly 2 miles, with about 400 feet of elevation gain and loss. For an even lighter experience, you may simply walk about a mile out and back along the same well-established trail, enjoying views on a clear day.

Regardless of the route you choose, weather permitting, as you approach Monte Grosso, you’ll be rewarded with sweeping views over the Gulf of Catania and across dramatic volcanic terrain—including hornitos, pyroclastic cones, lava flows, and flow channels. The trail is named in honor of Carlo Gemmellaro, a 19th-century professor of natural history, geology, and mineralogy at the University of Catania, whose work helped establish a globally respected geological school. The route features mixed terrain, from wide to narrow paths of lava gravel, and passes through vegetation such as pine and broom.

Almost constant volcanic activity has blessed Etna’s slopes with rich, fertile soils, ideal for agriculture, orchards, and vineyards. Around midday, arrive at one of the many emerging wineries on Etna’s flanks, where you’ll enjoy a light lunch and wine tasting. The location offers striking views—vineyards on one side, the volcano on the other.

Return to your country house hotel with time to relax and refresh before heading out for another dinner that celebrates the rich bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

3-4 mile options, easy to moderate (with some challenging terrain), 350-ft. elevation gain and 1,000-ft. elevation loss

Awaken at your tranquil resort to a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries, and bread—accompanied, of course, by a cappuccino or espresso. Then travel about 60–75 minutes to your trailhead in Ramacca, just west of the Plain of Catania. This area is renowned for both its archaeological and agricultural significance. Your pathway leads through the hilly landscape of the Erei Mountains, where gypsum rock appears in striking formations of coarse crystals, such as selenite (also known as moonstone). Along the way, luxuriant stands of olivastri, oaks, prickly pears, carob, citrus orchards, and oleanders mark your progress.

The trail culminates beneath the imposing Serravalle Castle, a medieval gem that has belonged to the Grimaldi family since the early 1500s.

You are warmly welcomed at a splendid estate owned by your local hosts, Gerardo and Mariarosa, where you refuel with a lunch of Sicilian specialties. Afterward, explore their expansive citrus groves and learn about the innovative techniques they’ve adopted to manage the growing challenges of climate change in the region.

Later, travel approximately 75 minutes to the valley of Noto—much of which is a UNESCO World Heritage site, recognized for its extraordinary late Baroque architecture rebuilt after the devastating 1693 earthquake. Arrive in the late afternoon to the hilltop town of Ragusa. Ragusa Ibla, the Old Town, was a key part of this Baroque renaissance, and you’ll have time to explore its winding streets up close tomorrow.

Your accommodations—a former palace—place you near the heart of the spectacular Old Town. The hotel blends modern comfort with historical charm, thoughtfully renovated to preserve its heritage while incorporating stylish contemporary design. After settling in and refreshing, rejoin your fellow travelers and leaders for a festive dinner featuring traditional regional fare at a restaurant steeped in local character. A leisurely stroll back to the hotel is the perfect close to your day.

Included Meals: Breakfast, Lunch, Dinner

3-5 miles, easy to moderate (with challenging sections), 350-ft. maximum elevation gain and 1,100-1,250-ft elevation loss, and 1-2 miles, easy

After savoring a breakfast of traditional local products, set out for a hike along the scenic pathways of the Cava della Misericordia, or Cave of Mercy. Your leaders will share details about the walk options available in the area. The trail winds through forests of pine, poplar, and oak, following an ancient quarry that bears traces of early human settlement. As you descend, pass the Benedictine convent and the ruins of old mills and stone houses. In spring, the route bursts with wildflowers—orchids, poppies, and wild asparagus creating a colorful display.

Continue on to Ragusa Ibla and explore this architectural gem with your leaders. Wander its elegant streets, home to some of the finest examples of late European Baroque design. Take time to enjoy lunch on your own at one of the many welcoming trattorias.

In the afternoon, reunite with your fellow travelers for a visit to an artisan studio, where you’ll learn about the tradition of the Carretti Siciliani—the famed Sicilian horse carts, intricately painted to depict themes of chivalry, faith, honor, and justice.

The rest of the day is yours to enjoy at your leisure. Continue exploring the charming streets of Ragusa Ibla, or return to the hotel to unwind. At De Stefano Palace, an elegant spa and wellness center invite you to relax and rejuvenate (treatments at your own expense). The facility features a Turkish bath, a saltwater heated pool, an emotional shower, a relaxation area with herbal teas, and a menu of treatments designed for both body and face.

Dinner is on your own this evening, with recommendations from your leaders to guide your culinary exploration.

Included Meals: Breakfast

5 miles, easy to moderate

After enjoying a leisurely breakfast, bid farewell to Ragusa and set off for one of southeastern Sicily’s most beautiful natural spots—the Oasi Nature Reserve at Vendicari. This marvelous coastal ecosystem, with its serene sandy beach and protected marshes, is home to a wide variety of migratory birds. Depending on the season and time of day, you may spot 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 this vantage point, you’ll enjoy sweeping views of the entire reserve—from the splendid Isle of Vendicari to Capo Passero on the horizon. You may even be tempted to take a swim!

Your trail concludes at a family-owned agriturismo, where you’ll enjoy a lunch of regional specialties—grilled vegetables, local Sicilian provola, pecorino, and tuma cheeses, and freshly made pasta.

After lunch, continue to Syracuse, a UNESCO World Heritage site. During the era of Magna Graecia, this city rivaled Athens as the most powerful in the ancient Greek world. Here, a local expert leads you on a guided tour of the Parco Archeologico della Neapolis—a treasure trove of Greek and Roman monuments. Highlights include the spectacular 5th-century BCE Greek Theater, still used for summer performances, and the nearby 2nd-century Roman Amphitheater (Anfiteatro Romano), the largest in Sicily and the third-largest in Italy. Unlike the Greek Theater, which celebrated art and drama, the Roman Amphitheater hosted brutal gladiator battles and slave punishments.

From here, continue to modern-day Syracuse, the cultural and administrative capital of southeastern Sicily. Known for its extravagant Baroque architecture, archaeological heritage, culinary delights, and coastal beauty, the city offers much to explore. Your home for the next two nights is on the island of Ortigia, the historical heart of Syracuse.

After settling in, enjoy an evening of independent exploration and dining. You might stroll through the Piazza del Duomo, widely regarded as one of Italy’s most beautiful squares. Surrounded by elegant Baroque buildings rebuilt after the 1693 earthquake, the plaza’s centerpiece is the Duomo (cathedral)—a striking fusion of architectural styles. Beneath its Baroque façade lie the remains of the 5th-century BCE Temple of Athena, including 26 preserved Doric columns visible both inside and out.

All roads from this piazza lead to dinner, and—as always—your leaders are happy to provide personalized recommendations to suit your preferences.

Included Meals: Breakfast, Lunch

1.5 miles, easy, 100-ft elevation gain and 300-ft elevation loss, or 2 miles, 450-ft elevation gain and 300-ft elevation loss, or 4 miles, moderate, 800-ft elevation gain and 700-ft. elevation loss

Start your day 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 filled with pistachio cream. Then, depart for one of Sicily’s most fascinating natural and archaeological treasures: the Necropolis of Pantalica.

Perched on a plateau between the canyons of the Anapo and Calcinara rivers, Pantalica was inhabited from prehistoric times through the Middle Ages. Its steep rock walls are carved with more than 5,000 tombs, dating as far back as the second millennium BCE—making it the largest burial complex of its kind in Sicily. Your walk options today range from one to three hours and lead through a dramatic, river-carved landscape of limestone cliffs, rich with colorful and fragrant Mediterranean vegetation.

Lunch is on your own in the quaint hilltop village of Ferla. Choose from local antipasti and pasta dishes or enjoy a simple panino and gelato on the terrace of a café or restaurant across from the town’s beautiful church.

After lunch, return to Ortigia and take time to relax and refresh. This evening, gather with your fellow travelers for a memorable farewell dinner featuring fresh local seafood and crisp white wine—a perfect toast to the week’s discoveries.

Included Meals: Breakfast, Dinner

After savoring breakfast at your hotel, bid farewell to your leaders and fellow travelers as your Sicilian journey comes to a close. Whether you’re heading to Catania or continuing onward, the hotel staff will be happy to assist with arranging transportation. Check-out time is 11:00 a.m., allowing you a leisurely departure as you prepare for your flight or rail connections.

Included Meals: Breakfast

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

Meet your fellow travelers and your Country Walkers leaders in the lobby of our pre-tour hotel, Hotel Monte Tauro in Taormina, at 8:30 a.m. with your luggage. Please be dressed for hiking—appropriate attire, sturdy footwear, and a daypack (to carry rain gear and a water bottle) are required.

Departing Taormina, a short drive brings you to your first trailhead in the foothills of Mt. Etna’s quiet, picturesque northern slopes. Etna’s majestic cone—the highest peak in Sicily and one of Europe’s largest active volcanoes—rises over 11,000 feet and spans an area greater than metropolitan New York. Its dramatic alpine landscapes reflect a striking mix of serene natural beauty and powerful geologic activity.

Hiking routes on or near the volcano’s slopes today are weather- and volcano-dependent, but may include an easy trail beginning in Linguaglossa, winding through hazelnut and olive groves and along part of a converted rail trail to the village of Castiglione di Sicilia. Known as “the quastallum” (or “the castle”) by a renowned Arab geographer, this scenic town sits on a hill between the Alcantara Valley and Etna Park, offering lovely views among fruit trees, vineyards, and ancient lava flows.

Upon arrival in Castiglione, you’ll meet your dedicated driver and transfer across the valley to the medieval village of Motta Camastra. Here, you are welcomed with a Sicilian-style lunch of crusty bread, olives, seasonal fruit, cured meats, pasta, and cheeses—served under a vine-covered pergola.

This memorable meal is part of a unique social dining project called Le Mamme del Borgo (“The Mothers of the Village”), which blends traditional Sicilian cuisine with moments of shared joy, local ingredients, and authentic connection to the community. By dining here, you are helping support this meaningful initiative and enjoying a deeper experience of local culture. Guests are welcome to step into the simple kitchen for a closer look at how these time-honored dishes are prepared.

After lunch, enjoy a guided stroll through Motta Camastra’s atmospheric streets—made famous as the fictional town of Corleone in The Godfather. Keep an eye out for colorful local characters and enjoy the village’s warm hospitality.

Later this afternoon, travel to your home-away-from-home for the next two nights: a family-owned boutique country hotel nestled among vineyards and citrus groves. Settle in, then gather poolside for a welcome aperitivo, followed by a delicious dinner at the hotel’s Michelin-starred restaurant. Savor innovative Sicilian fare paired with wines from the fertile volcanic slopes nearby.

Included Meals: Lunch, Dinner

2-5 miles, moderate to challenging, 400-1,000 ft. maximum elevation gain and loss

Following a delicious breakfast, begin your day with a drive to Mt. Etna’s picturesque southern slopes. Hiking options today are again weather- and volcano-dependent and may include trails above the town of Nicolosi—gateway to many excursions on the volcano and home to the Museum of Etna, which highlights both the geologic and cultural history of this remarkable site.

Your featured trail begins at an elevation of just over 4,000 feet and offers flexibility in both distance and elevation, accommodating a variety of hiking preferences. Those seeking a challenge can hike around Monte Gemmellaro—formed during an 1886 eruption—on a full 5-mile circuit with approximately 1,000 feet of elevation gain and loss. A shorter option around Monte Grosso spans roughly 2 miles, with about 400 feet of elevation gain and loss. For an even lighter experience, you may simply walk about a mile out and back along the same well-established trail, enjoying views on a clear day.

Regardless of the route you choose, weather permitting, as you approach Monte Grosso, you’ll be rewarded with sweeping views over the Gulf of Catania and across dramatic volcanic terrain—including hornitos, pyroclastic cones, lava flows, and flow channels. The trail is named in honor of Carlo Gemmellaro, a 19th-century professor of natural history, geology, and mineralogy at the University of Catania, whose work helped establish a globally respected geological school. The route features mixed terrain, from wide to narrow paths of lava gravel, and passes through vegetation such as pine and broom.

Almost constant volcanic activity has blessed Etna’s slopes with rich, fertile soils, ideal for agriculture, orchards, and vineyards. Around midday, arrive at one of the many emerging wineries on Etna’s flanks, where you’ll enjoy a light lunch and wine tasting. The location offers striking views—vineyards on one side, the volcano on the other.

Return to your country house hotel with time to relax and refresh before heading out for another dinner that celebrates the rich bounty of the region.

Included Meals: Breakfast, Lunch, Dinner

3-4 mile options, easy to moderate (with some challenging terrain), 350-ft. elevation gain and 1,000-ft. elevation loss

Awaken at your tranquil resort to a delicious breakfast of eggs, local cheeses and cured meats, fresh seasonal fruits, yogurt, pastries, and bread—accompanied, of course, by a cappuccino or espresso. Then travel about 60–75 minutes to your trailhead in Ramacca, just west of the Plain of Catania. This area is renowned for both its archaeological and agricultural significance. Your pathway leads through the hilly landscape of the Erei Mountains, where gypsum rock appears in striking formations of coarse crystals, such as selenite (also known as moonstone). Along the way, luxuriant stands of olivastri, oaks, prickly pears, carob, citrus orchards, and oleanders mark your progress.

The trail culminates beneath the imposing Serravalle Castle, a medieval gem that has belonged to the Grimaldi family since the early 1500s.

You are warmly welcomed at a splendid estate owned by your local hosts, Gerardo and Mariarosa, where you refuel with a lunch of Sicilian specialties. Afterward, explore their expansive citrus groves and learn about the innovative techniques they’ve adopted to manage the growing challenges of climate change in the region.

Later, travel approximately 75 minutes to the valley of Noto—much of which is a UNESCO World Heritage site, recognized for its extraordinary late Baroque architecture rebuilt after the devastating 1693 earthquake. Arrive in the late afternoon to the hilltop town of Ragusa. Ragusa Ibla, the Old Town, was a key part of this Baroque renaissance, and you’ll have time to explore its winding streets up close tomorrow.

Your accommodations—a former palace—place you near the heart of the spectacular Old Town. The hotel blends modern comfort with historical charm, thoughtfully renovated to preserve its heritage while incorporating stylish contemporary design. After settling in and refreshing, rejoin your fellow travelers and leaders for a festive dinner featuring traditional regional fare at a restaurant steeped in local character. A leisurely stroll back to the hotel is the perfect close to your day.

Included Meals: Breakfast, Lunch, Dinner

3-5 miles, easy to moderate (with challenging sections), 350-ft. maximum elevation gain and 1,100-1,250-ft elevation loss, and 1-2 miles, easy

After savoring a breakfast of traditional local products, set out for a hike along the scenic pathways of the Cava della Misericordia, or Cave of Mercy. Your leaders will share details about the walk options available in the area. The trail winds through forests of pine, poplar, and oak, following an ancient quarry that bears traces of early human settlement. As you descend, pass the Benedictine convent and the ruins of old mills and stone houses. In spring, the route bursts with wildflowers—orchids, poppies, and wild asparagus creating a colorful display.

Continue on to Ragusa Ibla and explore this architectural gem with your leaders. Wander its elegant streets, home to some of the finest examples of late European Baroque design. Take time to enjoy lunch on your own at one of the many welcoming trattorias.

In the afternoon, reunite with your fellow travelers for a visit to an artisan studio, where you’ll learn about the tradition of the Carretti Siciliani—the famed Sicilian horse carts, intricately painted to depict themes of chivalry, faith, honor, and justice.

The rest of the day is yours to enjoy at your leisure. Continue exploring the charming streets of Ragusa Ibla, or return to the hotel to unwind. At De Stefano Palace, an elegant spa and wellness center invite you to relax and rejuvenate (treatments at your own expense). The facility features a Turkish bath, a saltwater heated pool, an emotional shower, a relaxation area with herbal teas, and a menu of treatments designed for both body and face.

Dinner is on your own this evening, with recommendations from your leaders to guide your culinary exploration.

Included Meals: Breakfast

5 miles, easy to moderate

After enjoying a leisurely breakfast, bid farewell to Ragusa and set off for one of southeastern Sicily’s most beautiful natural spots—the Oasi Nature Reserve at Vendicari. This marvelous coastal ecosystem, with its serene sandy beach and protected marshes, is home to a wide variety of migratory birds. Depending on the season and time of day, you may spot 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 this vantage point, you’ll enjoy sweeping views of the entire reserve—from the splendid Isle of Vendicari to Capo Passero on the horizon. You may even be tempted to take a swim!

Your trail concludes at a family-owned agriturismo, where you’ll enjoy a lunch of regional specialties—grilled vegetables, local Sicilian provola, pecorino, and tuma cheeses, and freshly made pasta.

After lunch, continue to Syracuse, a UNESCO World Heritage site. During the era of Magna Graecia, this city rivaled Athens as the most powerful in the ancient Greek world. Here, a local expert leads you on a guided tour of the Parco Archeologico della Neapolis—a treasure trove of Greek and Roman monuments. Highlights include the spectacular 5th-century BCE Greek Theater, still used for summer performances, and the nearby 2nd-century Roman Amphitheater (Anfiteatro Romano), the largest in Sicily and the third-largest in Italy. Unlike the Greek Theater, which celebrated art and drama, the Roman Amphitheater hosted brutal gladiator battles and slave punishments.

From here, continue to modern-day Syracuse, the cultural and administrative capital of southeastern Sicily. Known for its extravagant Baroque architecture, archaeological heritage, culinary delights, and coastal beauty, the city offers much to explore. Your home for the next two nights is on the island of Ortigia, the historical heart of Syracuse.

After settling in, enjoy an evening of independent exploration and dining. You might stroll through the Piazza del Duomo, widely regarded as one of Italy’s most beautiful squares. Surrounded by elegant Baroque buildings rebuilt after the 1693 earthquake, the plaza’s centerpiece is the Duomo (cathedral)—a striking fusion of architectural styles. Beneath its Baroque façade lie the remains of the 5th-century BCE Temple of Athena, including 26 preserved Doric columns visible both inside and out.

All roads from this piazza lead to dinner, and—as always—your leaders are happy to provide personalized recommendations to suit your preferences.

Included Meals: Breakfast, Lunch

1.5 miles, easy, 100-ft elevation gain and 300-ft elevation loss, or 2 miles, 450-ft elevation gain and 300-ft elevation loss, or 4 miles, moderate, 800-ft elevation gain and 700-ft. elevation loss

Start your day 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 filled with pistachio cream. Then, depart for one of Sicily’s most fascinating natural and archaeological treasures: the Necropolis of Pantalica.

Perched on a plateau between the canyons of the Anapo and Calcinara rivers, Pantalica was inhabited from prehistoric times through the Middle Ages. Its steep rock walls are carved with more than 5,000 tombs, dating as far back as the second millennium BCE—making it the largest burial complex of its kind in Sicily. Your walk options today range from one to three hours and lead through a dramatic, river-carved landscape of limestone cliffs, rich with colorful and fragrant Mediterranean vegetation.

Lunch is on your own in the quaint hilltop village of Ferla. Choose from local antipasti and pasta dishes or enjoy a simple panino and gelato on the terrace of a café or restaurant across from the town’s beautiful church.

After lunch, return to Ortigia and take time to relax and refresh. This evening, gather with your fellow travelers for a memorable farewell dinner featuring fresh local seafood and crisp white wine—a perfect toast to the week’s discoveries.

Included Meals: Breakfast, Dinner

After savoring breakfast at your hotel, bid farewell to your leaders and fellow travelers as your Sicilian journey comes to a close. Whether you’re heading to Catania or continuing onward, the hotel staff will be happy to assist with arranging transportation. Check-out time is 11:00 a.m., allowing you a leisurely departure as you prepare for your flight or rail connections.

Included Meals: Breakfast