Italy: Matera, Otranto & the Puglia Coast

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

A Country Walkers representative will greet you at the airport to start your adventure off right. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

Parco Regionale della Murgia Materana; 2 miles, easy to moderate and Matera Guided Walking Tour; 2 miles, easy

After enjoying an included breakfast at your hotel, your leaders will meet you at 8:30 a.m.  in the lobby of Hotel Grande Albergo delle Nazioni in Bari. They’ll be wearing Country Walkers shirts. Please be dressed for walking—hiking shoes are required.

From Bari, you’ll travel to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was known as Lucania. Even today, locals still identify as Lucanian—a reflection of their cultural pride and deeply rooted culinary traditions.

This morning’s trail begins in the Parco Regionale della Murgia Materana, a magnificent landscape shaped by the Bradano River and the smaller streams of Gravina and Jesce. Home to a rich diversity of flora and fauna, this 17,000-acre park boasts 1,200 botanical species—representing one-sixth of Italy’s plant life and one-third of the region’s. Foxes, hares, porcupines, wild boars, and wildcats roam the terrain, while raptors such as the Lanner falcon, Egyptian vulture, and lesser kestrel circle above.

Your first walk offers a powerful sense of timelessness as you explore mystical abandoned caves and ghost villages. The park is dotted with jazzi—primitive, communal settlements where shepherds once lived alongside their livestock well into the 20th century. But perhaps even more captivating are the chiese rupestri, or rock-carved cave churches, which you’ll explore later this afternoon with a local guide.

The morning trail takes you through the Neolithic village of Murgia Timone and up to a breathtaking Belvedere, or scenic overlook. This is where the crucifixion scene in The Passion of the Christ was filmed, and it offers an unforgettable view of Matera and the steep ravine that surrounds it. After time to take in the panorama, you’ll retrace your steps and meet your minibus for a short transfer into the heart of Matera.

Lunch is at one of our favorite local restaurants, where you’ll enjoy a flavorful spread of Lucanian antipasti—perhaps salami with fennel, lampascioni (a wild onion related to garlic), sun-dried tomatoes, seasonal greens, and a selection of local cheeses like pecorino, caciocavallo, and caprino.

Following lunch, you’ll be introduced to Matera on a guided walking tour with a wonderful local expert. One of the oldest continuously inhabited cities in the world, Matera is a fascinating blend of past and present. As you walk, you’ll learn about the former cave dwellers and their communal lifestyle—where an “open door” spirit welcomed neighbors and strangers alike. From the cathedral, follow winding alleyways and hidden courtyards into the Sasso Barisano, where pale stone dwellings seem to grow organically from the rock. This is the sassi—literally “the stones”—a hauntingly beautiful setting that famously stood in for ancient Jerusalem in The Passion of the Christ.

Your walk ends at your luxury albergo diffuso, a boutique hotel spread across a series of cave dwellings carved into the soft tuff rock. After settling in and refreshing, you’ll rejoin your leaders and fellow travelers for a welcome aperitivo, soaking in the sassi’s iconic architectural profile. Then, sit down to a special seasonal dinner and a glass (or two) of the local Primitivo wine, enjoyed in a beautifully restored ancient mill.

Included Meals: Breakfast, Lunch, Dinner

4 miles, easy to moderate

Begin your day with a generous breakfast of regional cheeses and local delicacies, alongside a tempting spread of yogurt, cereals, fresh juices, eggs made to order, flaky pastries, and seasonal fruits—topped off, of course, with a perfectly brewed cappuccino.

After a short walk through the winding alleyways of Matera’s historic center to meet up with your minibus and dedicated driver, you’ll set off on a scenic 30-minute drive to Gravina in Puglia. Your route today begins on a hill overlooking Gravina’s old town. From here, follow a peaceful, mostly flat trail through the surrounding countryside, where olive trees and traditional dry stone walls line your path. Along the way, enjoy sweeping views and, time permitting, a detour to the archaeological site of Botromagno, a place rich with history and atmosphere.

The route continues downhill to one of Gravina’s most iconic landmarks: the Ponte Acquedotto, also known as Ponte Viadotto. This dramatic 18th-century aqueduct bridge—featured in the James Bond film No Time To Die—spans the canyon that separates the rock-cut churches of the eastern cliffs from the city center. Towering 121 feet high and stretching 295 feet across, it offers unforgettable views of the gorge below.

After crossing the bridge, it’s just a short walk into the heart of the Old Town, where you’ll stop for lunch at a beloved local restaurant run by our friend. Refuel with a seasonal feast: a colorful assortment of antipasti—perhaps including the renowned pallone di Gravina cheese—followed by a handmade pasta dish featuring fresh, local vegetables, and a lovingly prepared dolce di casa to finish.

Returning to Matera in the mid-afternoon, you’ll have time to further explore this remarkable city. Visit the Museum of Contemporary Sculpture, set in a series of dramatic cave spaces, or descend into the vast underground Palombaro Lungo, Matera’s largest ancient water cistern. Or, if you prefer, simply unwind at your hotel before heading out for an evening of independent exploration and dining—your leaders will be happy to offer recommendations.

Included Meals: Breakfast, Lunch

4 miles, easy

Today, you leave behind the cultural richness of Matera and travel to the lush Valle d’Itria in central Puglia. This picturesque valley, blanketed with vineyards and ancient olive groves, is famous for its hundreds of trulli—curious stone dwellings once used by Apulian farmers. These beehive-like structures feature circular, whitewashed walls and distinctive cone-shaped roofs. Built without mortar, they were cleverly designed to be dismantled quickly—an ingenious workaround to avoid property taxes. Look closely at the rooftops, where you’ll spot Paleo-Christian good-luck symbols painted in white.

Your walk begins near the 11th-century Church of Santa Maria di Barsento, not far from the village of Alberobello. From here, a scenic trail winds through green pastures and woodlands, and along quiet country lanes lined with stone walls, olive trees, and scattered trulli. Soon, you’ll arrive in Alberobello, a UNESCO World Heritage site where the streets are truly packed with these whimsical stone dwellings.

One of these trulli has been transformed into a charming enoteca and specialty shop, where you’ll meet Gino for an olive oil tasting paired with a light lunch of traditional Apulian snacks.

After lunch, enjoy time to explore this storybook town on your own. Your leaders will provide an orientation to help you navigate. You might wander to Piazza del Popolo (People’s Square) to browse artisanal boutiques offering hand-woven linens, filet lace, and colorful ceramics. Or, pay a visit to the Church of St. Anthony, which mirrors the architectural style of the surrounding trulli. For a sweet finish, stop by Pasticceria Martinucci for a delicious gelato.

Later this afternoon, continue your journey to Ostuni, known as the “White City” for its dazzling whitewashed buildings. After settling into your hotel, join your leaders for a stroll through this hilltop town with sweeping views of the Adriatic coast. Admire landmarks like the impressive 15th-century Ostuni Cathedral, the Bishop’s Palace, and other historic palazzi—elegant reminders of the noble families who once called this town home.

Afterward, enjoy an aperitivo or browse the local shops for beautifully crafted ceramics. For dinner on your own, consider one of your leaders’ favorite osterias along the route. Alternatively, unwind at the hotel’s spa and dine at the hotel’s acclaimed bistrot for a relaxing evening in.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take time to enjoy a leisurely breakfast. After bidding farewell to Ostuni, you journey south toward the medieval port town of Otranto, where you’ll be staying for the next few nights. Along the way, you’ll stop near Uggiano la Chiesa at a peaceful estate nestled among olive groves and Mediterranean macchia (scrubland).

This special property is the award-winning passion project, and Country Walkers’ Responsible Travel Initiative in the region, of sisters Giulia and Lucia Starace, who are preserving traditional textile arts for future generations. Here, a dedicated team of weavers teaches local children about age-old craftsmanship and the values of responsible culture. Country Walkers is proud to support the Le Costantine Foundation with a donation made on behalf of each guest on this tour. On arrival, stroll through a landscape dotted with myrtle, holm oaks, wild orchids, and one of the region’s oldest beehives. At the heart of the estate, enjoy a demonstration at the cooperative weaving studio, which recently contributed to the cruise collection of Parisian fashion house Dior. Afterwards, savor a delicious lunch on the grounds of this inspiring property.

In the afternoon, set off on foot for an easy walk back in time to the Bronze Age. Your destination is Italy’s megalithic garden in and around nearby Giurdignano, home to more than 25 menhirs and dolmens—mysterious standing stones that offer a fascinating glimpse into prehistoric life.

Continue your exploration with a visit to a 16th-century underground olive mill, and the evocative crypt of San Salvatore, dating back to the 8th century and adorned with remarkably well-preserved 13th-century frescoes.

Your walk concludes at a stunning whitewashed masseria just outside Otranto. On arrival, enjoy a sommelier-guided wine tasting paired with traditional Salentino snacks. Dinner is on your own this evening; a complimentary shuttle into town is available, or you may choose to dine at the masseria’s excellent on-site restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you set out for Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a striking location on the Strait of Otranto, where the Adriatic and Ionian seas meet. Greeks, Romans, Byzantines, Normans, and Aragonese have all laid claim to this strategic port, leaving behind a rich and layered history.

This morning’s walking route traces the rugged Adriatic shoreline, passing dramatic coves and sea-carved caves. Along the way, you’ll encounter the aromatic macchia—the hardy Mediterranean scrubland—and a series of ancient watchtowers, once vital to defending the coast from Turkish incursions. The stark, rocky landscape paired with the shimmering sea eventually leads you to a striking, abandoned bauxite quarry. Once a source of stone shipped as far as Venice for building the Republic’s grandeur, today it’s a surreal basin with crimson walls surrounding a bright, still lake—hence its nickname, Red Lake.

From here, continue on toward the Punta Palascia lighthouse, Italy’s easternmost point. After visiting the lighthouse, travel by minibus to a welcoming, family-run agriturismo, where a local cheesemaker invites you in for a demonstration and a light lunch featuring regional specialties—antipasti salentini, fresh cheeses, and homemade bread.

Later, travel on foot or by minibus to Porto Badisco, a picturesque bay where clear turquoise waters and a white-sand seabed invite you for a refreshing swim. According to Virgil, this was the site where Aeneas first landed after fleeing the fall of Troy.

Upon returning to the hotel, enjoy some time to unwind—perhaps poolside or with a relaxing massage—before heading to a nearby masseria for dinner. This warm, authentic experience is sure to be a highlight of your adventure.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and 1-2 miles, easy

On today’s walk, you’ll trace routes of historical and environmental significance along Puglia’s southernmost coast, through the Parco Naturale Regionale Costa Otranto–Santa Maria di Leuca e Bosco di Tricase. After enjoying a hearty breakfast, you’ll travel to the outskirts of Corsano to begin your uniquely rewarding day.

You start along a rocky, single-track coastal trail, which may be dotted with spring wildflowers and infused with the fragrant scent of Mediterranean macchia. Along the way, you’ll pass typical Salento pajare—dry-stone structures similar to the trulli of Alberobello. These may have originally served as temporary shelters, agricultural storehouses, or dwellings for farm workers. Your path, or tratturo as it’s locally known, follows the ancient Via del Sale (“Salt Route” or “Way”), once used by workers to transport salt harvested from sea water and dried in large cliffside tanks. These laborers were nicknamed Carcagni Tosti (“hard heels”) for their barefoot treks along the rocky coast.

Your trail culminates at Torre Specchia Ruggeri, an ancient watchtower built in 1568 to defend the coast from Saracen invasions. From here, continue by minibus to Santa Maria di Leuca, often referred to as the white pearl of Puglia.

This is the point where the Adriatic and Ionian seas swirl together, and the southernmost tip of the Via Francigena. This ancient pilgrimage route—whose name means “the road from France”—stretches from Canterbury to Rome and continues through Puglia, where pilgrims once sailed onward to the Holy Land. Over the centuries, traders, pirates, and invaders have all left their mark on the history and culture of Capo di Leuca.

Upon arrival, visit the impressive Basilica di Finibus Terrae, perched above the town’s harbor. Its name translates to “basilica at the end of the earth,” a fitting title for this windswept outpost at the edge of the Roman Empire. Your trip leaders will also offer an optional walk along the seaside promenade, highlighting local restaurants for lunch on your own. Later, return to your masseria for time to relax before dinner.

For your final dinner together, gather at the hotel’s al fresco restaurant, where you’ll be welcomed with a glass of sparkling prosecco. Settle in for a memorable meal that celebrates the seasonal bounty of the region. You might savor creamy troccoli pasta with cuttlefish and black chickpea cream, or risotto with Gallipoli’s violet shrimp, pistachios, and pesto—perfectly paired with a glass (or two) of local vino. It’s the ideal way to toast your journey through the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you’ll stop in the coastal port of Otranto for an hour-long walking tour with your leaders. This striking seaside town is known for its spectacular waterfront and rich medieval history. A highlight is the Otranto Cathedral, home to an extraordinary 8,611-square-foot mosaic depicting the Tree of Life, crafted by a monk in 1163.

Following the tour, enjoy free time to explore the town’s artisanal shops, where you’ll find clay whistles, woven baskets, hand-dyed fabrics, and traditional ceramics.

Your journey concludes in Lecce, often called the Florence of the South for its remarkable Baroque architecture. Bid farewell to your Country Walkers leaders at the post-tour hotel in Lecce by 12:30 p.m.

The remainder of the day is yours to uncover the wonders of this captivating city. Lunch and dinner are on your own, and we provide detailed city information to help you make the most of your stay.

Included Meals: Breakfast

Ciao! After an included breakfast this morning, complimentary transportation will be provided to Brindisi International Airport (approximately a 40-minute drive) or Bari Karol Wojtyła International Airport (approximately a two-hour drive), depending on your departure time.

Included Meals: Breakfast

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

A Country Walkers representative will greet you at the airport to start your adventure off right. A complimentary car service will whisk you to your centrally located hotel. From here, you are perfectly positioned to explore this charming city at your leisure.

Parco Regionale della Murgia Materana; 2 miles, easy to moderate and Matera Guided Walking Tour; 2 miles, easy

After enjoying an included breakfast at your hotel, your leaders will meet you at 8:30 a.m.  in the lobby of Hotel Grande Albergo delle Nazioni in Bari. They’ll be wearing Country Walkers shirts. Please be dressed for walking—hiking shoes are required.

From Bari, you’ll travel to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was known as Lucania. Even today, locals still identify as Lucanian—a reflection of their cultural pride and deeply rooted culinary traditions.

This morning’s trail begins in the Parco Regionale della Murgia Materana, a magnificent landscape shaped by the Bradano River and the smaller streams of Gravina and Jesce. Home to a rich diversity of flora and fauna, this 17,000-acre park boasts 1,200 botanical species—representing one-sixth of Italy’s plant life and one-third of the region’s. Foxes, hares, porcupines, wild boars, and wildcats roam the terrain, while raptors such as the Lanner falcon, Egyptian vulture, and lesser kestrel circle above.

Your first walk offers a powerful sense of timelessness as you explore mystical abandoned caves and ghost villages. The park is dotted with jazzi—primitive, communal settlements where shepherds once lived alongside their livestock well into the 20th century. But perhaps even more captivating are the chiese rupestri, or rock-carved cave churches, which you’ll explore later this afternoon with a local guide.

The morning trail takes you through the Neolithic village of Murgia Timone and up to a breathtaking Belvedere, or scenic overlook. This is where the crucifixion scene in The Passion of the Christ was filmed, and it offers an unforgettable view of Matera and the steep ravine that surrounds it. After time to take in the panorama, you’ll retrace your steps and meet your minibus for a short transfer into the heart of Matera.

Lunch is at one of our favorite local restaurants, where you’ll enjoy a flavorful spread of Lucanian antipasti—perhaps salami with fennel, lampascioni (a wild onion related to garlic), sun-dried tomatoes, seasonal greens, and a selection of local cheeses like pecorino, caciocavallo, and caprino.

Following lunch, you’ll be introduced to Matera on a guided walking tour with a wonderful local expert. One of the oldest continuously inhabited cities in the world, Matera is a fascinating blend of past and present. As you walk, you’ll learn about the former cave dwellers and their communal lifestyle—where an “open door” spirit welcomed neighbors and strangers alike. From the cathedral, follow winding alleyways and hidden courtyards into the Sasso Barisano, where pale stone dwellings seem to grow organically from the rock. This is the sassi—literally “the stones”—a hauntingly beautiful setting that famously stood in for ancient Jerusalem in The Passion of the Christ.

Your walk ends at your luxury albergo diffuso, a boutique hotel spread across a series of cave dwellings carved into the soft tuff rock. After settling in and refreshing, you’ll rejoin your leaders and fellow travelers for a welcome aperitivo, soaking in the sassi’s iconic architectural profile. Then, sit down to a special seasonal dinner and a glass (or two) of the local Primitivo wine, enjoyed in a beautifully restored ancient mill.

Included Meals: Breakfast, Lunch, Dinner

4 miles, easy to moderate

Begin your day with a generous breakfast of regional cheeses and local delicacies, alongside a tempting spread of yogurt, cereals, fresh juices, eggs made to order, flaky pastries, and seasonal fruits—topped off, of course, with a perfectly brewed cappuccino.

After a short walk through the winding alleyways of Matera’s historic center to meet up with your minibus and dedicated driver, you’ll set off on a scenic 30-minute drive to Gravina in Puglia. Your route today begins on a hill overlooking Gravina’s old town. From here, follow a peaceful, mostly flat trail through the surrounding countryside, where olive trees and traditional dry stone walls line your path. Along the way, enjoy sweeping views and, time permitting, a detour to the archaeological site of Botromagno, a place rich with history and atmosphere.

The route continues downhill to one of Gravina’s most iconic landmarks: the Ponte Acquedotto, also known as Ponte Viadotto. This dramatic 18th-century aqueduct bridge—featured in the James Bond film No Time To Die—spans the canyon that separates the rock-cut churches of the eastern cliffs from the city center. Towering 121 feet high and stretching 295 feet across, it offers unforgettable views of the gorge below.

After crossing the bridge, it’s just a short walk into the heart of the Old Town, where you’ll stop for lunch at a beloved local restaurant run by our friend. Refuel with a seasonal feast: a colorful assortment of antipasti—perhaps including the renowned pallone di Gravina cheese—followed by a handmade pasta dish featuring fresh, local vegetables, and a lovingly prepared dolce di casa to finish.

Returning to Matera in the mid-afternoon, you’ll have time to further explore this remarkable city. Visit the Museum of Contemporary Sculpture, set in a series of dramatic cave spaces, or descend into the vast underground Palombaro Lungo, Matera’s largest ancient water cistern. Or, if you prefer, simply unwind at your hotel before heading out for an evening of independent exploration and dining—your leaders will be happy to offer recommendations.

Included Meals: Breakfast, Lunch

4 miles, easy

Today, you leave behind the cultural richness of Matera and travel to the lush Valle d’Itria in central Puglia. This picturesque valley, blanketed with vineyards and ancient olive groves, is famous for its hundreds of trulli—curious stone dwellings once used by Apulian farmers. These beehive-like structures feature circular, whitewashed walls and distinctive cone-shaped roofs. Built without mortar, they were cleverly designed to be dismantled quickly—an ingenious workaround to avoid property taxes. Look closely at the rooftops, where you’ll spot Paleo-Christian good-luck symbols painted in white.

Your walk begins near the 11th-century Church of Santa Maria di Barsento, not far from the village of Alberobello. From here, a scenic trail winds through green pastures and woodlands, and along quiet country lanes lined with stone walls, olive trees, and scattered trulli. Soon, you’ll arrive in Alberobello, a UNESCO World Heritage site where the streets are truly packed with these whimsical stone dwellings.

One of these trulli has been transformed into a charming enoteca and specialty shop, where you’ll meet Gino for an olive oil tasting paired with a light lunch of traditional Apulian snacks.

After lunch, enjoy time to explore this storybook town on your own. Your leaders will provide an orientation to help you navigate. You might wander to Piazza del Popolo (People’s Square) to browse artisanal boutiques offering hand-woven linens, filet lace, and colorful ceramics. Or, pay a visit to the Church of St. Anthony, which mirrors the architectural style of the surrounding trulli. For a sweet finish, stop by Pasticceria Martinucci for a delicious gelato.

Later this afternoon, continue your journey to Ostuni, known as the “White City” for its dazzling whitewashed buildings. After settling into your hotel, join your leaders for a stroll through this hilltop town with sweeping views of the Adriatic coast. Admire landmarks like the impressive 15th-century Ostuni Cathedral, the Bishop’s Palace, and other historic palazzi—elegant reminders of the noble families who once called this town home.

Afterward, enjoy an aperitivo or browse the local shops for beautifully crafted ceramics. For dinner on your own, consider one of your leaders’ favorite osterias along the route. Alternatively, unwind at the hotel’s spa and dine at the hotel’s acclaimed bistrot for a relaxing evening in.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take time to enjoy a leisurely breakfast. After bidding farewell to Ostuni, you journey south toward the medieval port town of Otranto, where you’ll be staying for the next few nights. Along the way, you’ll stop near Uggiano la Chiesa at a peaceful estate nestled among olive groves and Mediterranean macchia (scrubland).

This special property is the award-winning passion project, and Country Walkers’ Responsible Travel Initiative in the region, of sisters Giulia and Lucia Starace, who are preserving traditional textile arts for future generations. Here, a dedicated team of weavers teaches local children about age-old craftsmanship and the values of responsible culture. Country Walkers is proud to support the Le Costantine Foundation with a donation made on behalf of each guest on this tour. On arrival, stroll through a landscape dotted with myrtle, holm oaks, wild orchids, and one of the region’s oldest beehives. At the heart of the estate, enjoy a demonstration at the cooperative weaving studio, which recently contributed to the cruise collection of Parisian fashion house Dior. Afterwards, savor a delicious lunch on the grounds of this inspiring property.

In the afternoon, set off on foot for an easy walk back in time to the Bronze Age. Your destination is Italy’s megalithic garden in and around nearby Giurdignano, home to more than 25 menhirs and dolmens—mysterious standing stones that offer a fascinating glimpse into prehistoric life.

Continue your exploration with a visit to a 16th-century underground olive mill, and the evocative crypt of San Salvatore, dating back to the 8th century and adorned with remarkably well-preserved 13th-century frescoes.

Your walk concludes at a stunning whitewashed masseria just outside Otranto. On arrival, enjoy a sommelier-guided wine tasting paired with traditional Salentino snacks. Dinner is on your own this evening; a complimentary shuttle into town is available, or you may choose to dine at the masseria’s excellent on-site restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you set out for Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a striking location on the Strait of Otranto, where the Adriatic and Ionian seas meet. Greeks, Romans, Byzantines, Normans, and Aragonese have all laid claim to this strategic port, leaving behind a rich and layered history.

This morning’s walking route traces the rugged Adriatic shoreline, passing dramatic coves and sea-carved caves. Along the way, you’ll encounter the aromatic macchia—the hardy Mediterranean scrubland—and a series of ancient watchtowers, once vital to defending the coast from Turkish incursions. The stark, rocky landscape paired with the shimmering sea eventually leads you to a striking, abandoned bauxite quarry. Once a source of stone shipped as far as Venice for building the Republic’s grandeur, today it’s a surreal basin with crimson walls surrounding a bright, still lake—hence its nickname, Red Lake.

From here, continue on toward the Punta Palascia lighthouse, Italy’s easternmost point. After visiting the lighthouse, travel by minibus to a welcoming, family-run agriturismo, where a local cheesemaker invites you in for a demonstration and a light lunch featuring regional specialties—antipasti salentini, fresh cheeses, and homemade bread.

Later, travel on foot or by minibus to Porto Badisco, a picturesque bay where clear turquoise waters and a white-sand seabed invite you for a refreshing swim. According to Virgil, this was the site where Aeneas first landed after fleeing the fall of Troy.

Upon returning to the hotel, enjoy some time to unwind—perhaps poolside or with a relaxing massage—before heading to a nearby masseria for dinner. This warm, authentic experience is sure to be a highlight of your adventure.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and 1-2 miles, easy

On today’s walk, you’ll trace routes of historical and environmental significance along Puglia’s southernmost coast, through the Parco Naturale Regionale Costa Otranto–Santa Maria di Leuca e Bosco di Tricase. After enjoying a hearty breakfast, you’ll travel to the outskirts of Corsano to begin your uniquely rewarding day.

You start along a rocky, single-track coastal trail, which may be dotted with spring wildflowers and infused with the fragrant scent of Mediterranean macchia. Along the way, you’ll pass typical Salento pajare—dry-stone structures similar to the trulli of Alberobello. These may have originally served as temporary shelters, agricultural storehouses, or dwellings for farm workers. Your path, or tratturo as it’s locally known, follows the ancient Via del Sale (“Salt Route” or “Way”), once used by workers to transport salt harvested from sea water and dried in large cliffside tanks. These laborers were nicknamed Carcagni Tosti (“hard heels”) for their barefoot treks along the rocky coast.

Your trail culminates at Torre Specchia Ruggeri, an ancient watchtower built in 1568 to defend the coast from Saracen invasions. From here, continue by minibus to Santa Maria di Leuca, often referred to as the white pearl of Puglia.

This is the point where the Adriatic and Ionian seas swirl together, and the southernmost tip of the Via Francigena. This ancient pilgrimage route—whose name means “the road from France”—stretches from Canterbury to Rome and continues through Puglia, where pilgrims once sailed onward to the Holy Land. Over the centuries, traders, pirates, and invaders have all left their mark on the history and culture of Capo di Leuca.

Upon arrival, visit the impressive Basilica di Finibus Terrae, perched above the town’s harbor. Its name translates to “basilica at the end of the earth,” a fitting title for this windswept outpost at the edge of the Roman Empire. Your trip leaders will also offer an optional walk along the seaside promenade, highlighting local restaurants for lunch on your own. Later, return to your masseria for time to relax before dinner.

For your final dinner together, gather at the hotel’s al fresco restaurant, where you’ll be welcomed with a glass of sparkling prosecco. Settle in for a memorable meal that celebrates the seasonal bounty of the region. You might savor creamy troccoli pasta with cuttlefish and black chickpea cream, or risotto with Gallipoli’s violet shrimp, pistachios, and pesto—perfectly paired with a glass (or two) of local vino. It’s the ideal way to toast your journey through the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you’ll stop in the coastal port of Otranto for an hour-long walking tour with your leaders. This striking seaside town is known for its spectacular waterfront and rich medieval history. A highlight is the Otranto Cathedral, home to an extraordinary 8,611-square-foot mosaic depicting the Tree of Life, crafted by a monk in 1163.

Following the tour, enjoy free time to explore the town’s artisanal shops, where you’ll find clay whistles, woven baskets, hand-dyed fabrics, and traditional ceramics.

Your journey concludes in Lecce, often called the Florence of the South for its remarkable Baroque architecture. Bid farewell to your Country Walkers leaders at the post-tour hotel in Lecce by 12:30 p.m.

The remainder of the day is yours to uncover the wonders of this captivating city. Lunch and dinner are on your own, and we provide detailed city information to help you make the most of your stay.

Included Meals: Breakfast

Ciao! After an included breakfast this morning, complimentary transportation will be provided to Brindisi International Airport (approximately a 40-minute drive) or Bari Karol Wojtyła International Airport (approximately a two-hour drive), depending on your departure time.

Included Meals: Breakfast

Parco Regionale della Murgia Materana; 2 miles, easy to moderate and Matera Guided Walking Tour; 2 miles, easy

Your leaders will meet you at 8:30 a.m. (after breakfast on your own) in the lobby of Hotel Grande Albergo delle Nazioni, Lungomare Nazario Sauro, 7, Bari. They’ll be wearing Country Walkers shirts. Please be dressed for walking—hiking shoes are required.

From Bari, you’ll travel to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was known as Lucania. Even today, locals still identify as Lucanian—a reflection of their cultural pride and deeply rooted culinary traditions.

This morning’s trail begins in the Parco Regionale della Murgia Materana, a magnificent landscape shaped by the Bradano River and the smaller streams of Gravina and Jesce. Home to a rich diversity of flora and fauna, this 17,000-acre park boasts 1,200 botanical species—representing one-sixth of Italy’s plant life and one-third of the region’s. Foxes, hares, porcupines, wild boars, and wildcats roam the terrain, while raptors such as the Lanner falcon, Egyptian vulture, and lesser kestrel circle above.

Your first walk offers a powerful sense of timelessness as you explore mystical abandoned caves and ghost villages. The park is dotted with jazzi—primitive, communal settlements where shepherds once lived alongside their livestock well into the 20th century. But perhaps even more captivating are the chiese rupestri, or rock-carved cave churches, which you’ll explore later this afternoon with a local guide.

The morning trail takes you through the Neolithic village of Murgia Timone and up to a breathtaking Belvedere, or scenic overlook. This is where the crucifixion scene in The Passion of the Christ was filmed, and it offers an unforgettable view of Matera and the steep ravine that surrounds it. After time to take in the panorama, you’ll retrace your steps and meet your minibus for a short transfer into the heart of Matera.

Lunch is at one of our favorite local restaurants, where you’ll enjoy a flavorful spread of Lucanian antipasti—perhaps salami with fennel, lampascioni (a wild onion related to garlic), sun-dried tomatoes, seasonal greens, and a selection of local cheeses like pecorino, caciocavallo, and caprino.

Following lunch, you’ll be introduced to Matera on a guided walking tour with a wonderful local expert. One of the oldest continuously inhabited cities in the world, Matera is a fascinating blend of past and present. As you walk, you’ll learn about the former cave dwellers and their communal lifestyle—where an “open door” spirit welcomed neighbors and strangers alike. From the cathedral, follow winding alleyways and hidden courtyards into the Sasso Barisano, where pale stone dwellings seem to grow organically from the rock. This is the sassi—literally “the stones”—a hauntingly beautiful setting that famously stood in for ancient Jerusalem in The Passion of the Christ.

Your walk ends at your luxury albergo diffuso, a boutique hotel spread across a series of cave dwellings carved into the soft tuff rock. After settling in and refreshing, you’ll rejoin your leaders and fellow travelers for a welcome aperitivo, soaking in the sassi’s iconic architectural profile. Then, sit down to a special seasonal dinner and a glass (or two) of the local Primitivo wine, enjoyed in a beautifully restored ancient mill.

Included Meals: Lunch, Dinner

4 miles, easy to moderate

Begin your day with a generous breakfast of regional cheeses and local delicacies, alongside a tempting spread of yogurt, cereals, fresh juices, eggs made to order, flaky pastries, and seasonal fruits—topped off, of course, with a perfectly brewed cappuccino.

After a short walk through the winding alleyways of Matera’s historic center to meet up with your minibus and dedicated driver, you’ll set off on a scenic 30-minute drive to Gravina in Puglia. Your route today begins on a hill overlooking Gravina’s old town. From here, follow a peaceful, mostly flat trail through the surrounding countryside, where olive trees and traditional dry stone walls line your path. Along the way, enjoy sweeping views and, time permitting, a detour to the archaeological site of Botromagno, a place rich with history and atmosphere.

The route continues downhill to one of Gravina’s most iconic landmarks: the Ponte Acquedotto, also known as Ponte Viadotto. This dramatic 18th-century aqueduct bridge—featured in the James Bond film No Time To Die—spans the canyon that separates the rock-cut churches of the eastern cliffs from the city center. Towering 121 feet high and stretching 295 feet across, it offers unforgettable views of the gorge below.

After crossing the bridge, it’s just a short walk into the heart of the Old Town, where you’ll stop for lunch at a beloved local restaurant run by our friend. Refuel with a seasonal feast: a colorful assortment of antipasti—perhaps including the renowned pallone di Gravina cheese—followed by a handmade pasta dish featuring fresh, local vegetables, and a lovingly prepared dolce di casa to finish.

Returning to Matera in the mid-afternoon, you’ll have time to further explore this remarkable city. Visit the Museum of Contemporary Sculpture, set in a series of dramatic cave spaces, or descend into the vast underground Palombaro Lungo, Matera’s largest ancient water cistern. Or, if you prefer, simply unwind at your hotel before heading out for an evening of independent exploration and dining—your leaders will be happy to offer recommendations.

Included Meals: Breakfast, Lunch

4 miles, easy

Today, you leave behind the cultural richness of Matera and travel to the lush Valle d’Itria in central Puglia. This picturesque valley, blanketed with vineyards and ancient olive groves, is famous for its hundreds of trulli—curious stone dwellings once used by Apulian farmers. These beehive-like structures feature circular, whitewashed walls and distinctive cone-shaped roofs. Built without mortar, they were cleverly designed to be dismantled quickly—an ingenious workaround to avoid property taxes. Look closely at the rooftops, where you’ll spot Paleo-Christian good-luck symbols painted in white.

Your walk begins near the 11th-century Church of Santa Maria di Barsento, not far from the village of Alberobello. From here, a scenic trail winds through green pastures and woodlands, and along quiet country lanes lined with stone walls, olive trees, and scattered trulli. Soon, you’ll arrive in Alberobello, a UNESCO World Heritage site where the streets are truly packed with these whimsical stone dwellings.

One of these trulli has been transformed into a charming enoteca and specialty shop, where you’ll meet Gino for an olive oil tasting paired with a light lunch of traditional Apulian snacks.

After lunch, enjoy time to explore this storybook town on your own. Your leaders will provide an orientation to help you navigate. You might wander to Piazza del Popolo (People’s Square) to browse artisanal boutiques offering hand-woven linens, filet lace, and colorful ceramics. Or, pay a visit to the Church of St. Anthony, which mirrors the architectural style of the surrounding trulli. For a sweet finish, stop by Pasticceria Martinucci for a delicious gelato.

Later this afternoon, continue your journey to Ostuni, known as the “White City” for its dazzling whitewashed buildings. After settling into your hotel, join your leaders for a stroll through this hilltop town with sweeping views of the Adriatic coast. Admire landmarks like the impressive 15th-century Ostuni Cathedral, the Bishop’s Palace, and other historic palazzi—elegant reminders of the noble families who once called this town home.

Afterward, enjoy an aperitivo or browse the local shops for beautifully crafted ceramics. For dinner on your own, consider one of your leaders’ favorite osterias along the route. Alternatively, unwind at the hotel’s spa and dine at the hotel’s acclaimed bistrot for a relaxing evening in.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take time to enjoy a leisurely breakfast. After bidding farewell to Ostuni, you journey south toward the medieval port town of Otranto, where you’ll be staying for the next few nights. Along the way, you’ll stop near Uggiano la Chiesa at a peaceful estate nestled among olive groves and Mediterranean macchia (scrubland).

This special property is the award-winning passion project, and Country Walkers’ Responsible Travel Initiative in the region, of sisters Giulia and Lucia Starace, who are preserving traditional textile arts for future generations. Here, a dedicated team of weavers teaches local children about age-old craftsmanship and the values of responsible culture. Country Walkers is proud to support the Le Costantine Foundation with a donation made on behalf of each guest on this tour. On arrival, stroll through a landscape dotted with myrtle, holm oaks, wild orchids, and one of the region’s oldest beehives. At the heart of the estate, enjoy a demonstration at the cooperative weaving studio, which recently contributed to the cruise collection of Parisian fashion house Dior. Afterwards, savor a delicious lunch on the grounds of this inspiring property.

In the afternoon, set off on foot for an easy walk back in time to the Bronze Age. Your destination is Italy’s megalithic garden in and around nearby Giurdignano, home to more than 25 menhirs and dolmens—mysterious standing stones that offer a fascinating glimpse into prehistoric life.

Continue your exploration with a visit to a 16th-century underground olive mill, and the evocative crypt of San Salvatore, dating back to the 8th century and adorned with remarkably well-preserved 13th-century frescoes.

Your walk concludes at a stunning whitewashed masseria just outside Otranto. On arrival, enjoy a sommelier-guided wine tasting paired with traditional Salentino snacks. Dinner is on your own this evening; a complimentary shuttle into town is available, or you may choose to dine at the masseria’s excellent on-site restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you set out for Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a striking location on the Strait of Otranto, where the Adriatic and Ionian seas meet. Greeks, Romans, Byzantines, Normans, and Aragonese have all laid claim to this strategic port, leaving behind a rich and layered history.

This morning’s walking route traces the rugged Adriatic shoreline, passing dramatic coves and sea-carved caves. Along the way, you’ll encounter the aromatic macchia—the hardy Mediterranean scrubland—and a series of ancient watchtowers, once vital to defending the coast from Turkish incursions. The stark, rocky landscape paired with the shimmering sea eventually leads you to a striking, abandoned bauxite quarry. Once a source of stone shipped as far as Venice for building the Republic’s grandeur, today it’s a surreal basin with crimson walls surrounding a bright, still lake—hence its nickname, Red Lake.

From here, continue on toward the Punta Palascia lighthouse, Italy’s easternmost point. After visiting the lighthouse, travel by minibus to a welcoming, family-run agriturismo, where a local cheesemaker invites you in for a demonstration and a light lunch featuring regional specialties—antipasti salentini, fresh cheeses, and homemade bread.

Later, travel on foot or by minibus to Porto Badisco, a picturesque bay where clear turquoise waters and a white-sand seabed invite you for a refreshing swim. According to Virgil, this was the site where Aeneas first landed after fleeing the fall of Troy.

Upon returning to the hotel, enjoy some time to unwind—perhaps poolside or with a relaxing massage—before heading to a nearby masseria for dinner. This warm, authentic experience is sure to be a highlight of your adventure.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and 1-2 miles, easy

On today’s walk, you’ll trace routes of historical and environmental significance along Puglia’s southernmost coast, through the Parco Naturale Regionale Costa Otranto–Santa Maria di Leuca e Bosco di Tricase. After enjoying a hearty breakfast, you’ll travel to the outskirts of Corsano to begin your uniquely rewarding day.

You start along a rocky, single-track coastal trail, which may be dotted with spring wildflowers and infused with the fragrant scent of Mediterranean macchia. Along the way, you’ll pass typical Salento pajare—dry-stone structures similar to the trulli of Alberobello. These may have originally served as temporary shelters, agricultural storehouses, or dwellings for farm workers. Your path, or tratturo as it’s locally known, follows the ancient Via del Sale (“Salt Route” or “Way”), once used by workers to transport salt harvested from sea water and dried in large cliffside tanks. These laborers were nicknamed Carcagni Tosti (“hard heels”) for their barefoot treks along the rocky coast.

Your trail culminates at Torre Specchia Ruggeri, an ancient watchtower built in 1568 to defend the coast from Saracen invasions. From here, continue by minibus to Santa Maria di Leuca, often referred to as the white pearl of Puglia.

This is the point where the Adriatic and Ionian seas swirl together, and the southernmost tip of the Via Francigena. This ancient pilgrimage route—whose name means “the road from France”—stretches from Canterbury to Rome and continues through Puglia, where pilgrims once sailed onward to the Holy Land. Over the centuries, traders, pirates, and invaders have all left their mark on the history and culture of Capo di Leuca.

Upon arrival, visit the impressive Basilica di Finibus Terrae, perched above the town’s harbor. Its name translates to “basilica at the end of the earth,” a fitting title for this windswept outpost at the edge of the Roman Empire. Your trip leaders will also offer an optional walk along the seaside promenade, highlighting local restaurants for lunch on your own. Later, return to your masseria for time to relax before dinner.

For your final dinner together, gather at the hotel’s al fresco restaurant, where you’ll be welcomed with a glass of sparkling prosecco. Settle in for a memorable meal that celebrates the seasonal bounty of the region. You might savor creamy troccoli pasta with cuttlefish and black chickpea cream, or risotto with Gallipoli’s violet shrimp, pistachios, and pesto—perfectly paired with a glass (or two) of local vino. It’s the ideal way to toast your journey through the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you’ll stop in the coastal port of Otranto for an hour-long walking tour with your leaders. This striking seaside town is known for its spectacular waterfront and rich medieval history. A highlight is the Otranto Cathedral, home to an extraordinary 8,611-square-foot mosaic depicting the Tree of Life, crafted by a monk in 1163.

Following the tour, enjoy free time to explore the town’s artisanal shops, where you’ll find clay whistles, woven baskets, hand-dyed fabrics, and traditional ceramics.

Your journey concludes in Lecce, often called the Florence of the South for its remarkable Baroque architecture. Bid farewell to your Country Walkers leaders at the post-tour hotel in Lecce by 12:30 p.m.

Included Meals: Breakfast

Parco Regionale della Murgia Materana; 2 miles, easy to moderate and Matera Guided Walking Tour; 2 miles, easy

Your leaders will meet you at 8:30 a.m. (after breakfast on your own) in the lobby of Hotel Grande Albergo delle Nazioni, Lungomare Nazario Sauro, 7, Bari. They’ll be wearing Country Walkers shirts. Please be dressed for walking—hiking shoes are required.

From Bari, you’ll travel to Basilicata, the only region in Italy with two names. Until 1945, this dramatically scenic and tranquil agrarian area was known as Lucania. Even today, locals still identify as Lucanian—a reflection of their cultural pride and deeply rooted culinary traditions.

This morning’s trail begins in the Parco Regionale della Murgia Materana, a magnificent landscape shaped by the Bradano River and the smaller streams of Gravina and Jesce. Home to a rich diversity of flora and fauna, this 17,000-acre park boasts 1,200 botanical species—representing one-sixth of Italy’s plant life and one-third of the region’s. Foxes, hares, porcupines, wild boars, and wildcats roam the terrain, while raptors such as the Lanner falcon, Egyptian vulture, and lesser kestrel circle above.

Your first walk offers a powerful sense of timelessness as you explore mystical abandoned caves and ghost villages. The park is dotted with jazzi—primitive, communal settlements where shepherds once lived alongside their livestock well into the 20th century. But perhaps even more captivating are the chiese rupestri, or rock-carved cave churches, which you’ll explore later this afternoon with a local guide.

The morning trail takes you through the Neolithic village of Murgia Timone and up to a breathtaking Belvedere, or scenic overlook. This is where the crucifixion scene in The Passion of the Christ was filmed, and it offers an unforgettable view of Matera and the steep ravine that surrounds it. After time to take in the panorama, you’ll retrace your steps and meet your minibus for a short transfer into the heart of Matera.

Lunch is at one of our favorite local restaurants, where you’ll enjoy a flavorful spread of Lucanian antipasti—perhaps salami with fennel, lampascioni (a wild onion related to garlic), sun-dried tomatoes, seasonal greens, and a selection of local cheeses like pecorino, caciocavallo, and caprino.

Following lunch, you’ll be introduced to Matera on a guided walking tour with a wonderful local expert. One of the oldest continuously inhabited cities in the world, Matera is a fascinating blend of past and present. As you walk, you’ll learn about the former cave dwellers and their communal lifestyle—where an “open door” spirit welcomed neighbors and strangers alike. From the cathedral, follow winding alleyways and hidden courtyards into the Sasso Barisano, where pale stone dwellings seem to grow organically from the rock. This is the sassi—literally “the stones”—a hauntingly beautiful setting that famously stood in for ancient Jerusalem in The Passion of the Christ.

Your walk ends at your luxury albergo diffuso, a boutique hotel spread across a series of cave dwellings carved into the soft tuff rock. After settling in and refreshing, you’ll rejoin your leaders and fellow travelers for a welcome aperitivo, soaking in the sassi’s iconic architectural profile. Then, sit down to a special seasonal dinner and a glass (or two) of the local Primitivo wine, enjoyed in a beautifully restored ancient mill.

Included Meals: Lunch, Dinner

4 miles, easy to moderate

Begin your day with a generous breakfast of regional cheeses and local delicacies, alongside a tempting spread of yogurt, cereals, fresh juices, eggs made to order, flaky pastries, and seasonal fruits—topped off, of course, with a perfectly brewed cappuccino.

After a short walk through the winding alleyways of Matera’s historic center to meet up with your minibus and dedicated driver, you’ll set off on a scenic 30-minute drive to Gravina in Puglia. Your route today begins on a hill overlooking Gravina’s old town. From here, follow a peaceful, mostly flat trail through the surrounding countryside, where olive trees and traditional dry stone walls line your path. Along the way, enjoy sweeping views and, time permitting, a detour to the archaeological site of Botromagno, a place rich with history and atmosphere.

The route continues downhill to one of Gravina’s most iconic landmarks: the Ponte Acquedotto, also known as Ponte Viadotto. This dramatic 18th-century aqueduct bridge—featured in the James Bond film No Time To Die—spans the canyon that separates the rock-cut churches of the eastern cliffs from the city center. Towering 121 feet high and stretching 295 feet across, it offers unforgettable views of the gorge below.

After crossing the bridge, it’s just a short walk into the heart of the Old Town, where you’ll stop for lunch at a beloved local restaurant run by our friend. Refuel with a seasonal feast: a colorful assortment of antipasti—perhaps including the renowned pallone di Gravina cheese—followed by a handmade pasta dish featuring fresh, local vegetables, and a lovingly prepared dolce di casa to finish.

Returning to Matera in the mid-afternoon, you’ll have time to further explore this remarkable city. Visit the Museum of Contemporary Sculpture, set in a series of dramatic cave spaces, or descend into the vast underground Palombaro Lungo, Matera’s largest ancient water cistern. Or, if you prefer, simply unwind at your hotel before heading out for an evening of independent exploration and dining—your leaders will be happy to offer recommendations.

Included Meals: Breakfast, Lunch

4 miles, easy

Today, you leave behind the cultural richness of Matera and travel to the lush Valle d’Itria in central Puglia. This picturesque valley, blanketed with vineyards and ancient olive groves, is famous for its hundreds of trulli—curious stone dwellings once used by Apulian farmers. These beehive-like structures feature circular, whitewashed walls and distinctive cone-shaped roofs. Built without mortar, they were cleverly designed to be dismantled quickly—an ingenious workaround to avoid property taxes. Look closely at the rooftops, where you’ll spot Paleo-Christian good-luck symbols painted in white.

Your walk begins near the 11th-century Church of Santa Maria di Barsento, not far from the village of Alberobello. From here, a scenic trail winds through green pastures and woodlands, and along quiet country lanes lined with stone walls, olive trees, and scattered trulli. Soon, you’ll arrive in Alberobello, a UNESCO World Heritage site where the streets are truly packed with these whimsical stone dwellings.

One of these trulli has been transformed into a charming enoteca and specialty shop, where you’ll meet Gino for an olive oil tasting paired with a light lunch of traditional Apulian snacks.

After lunch, enjoy time to explore this storybook town on your own. Your leaders will provide an orientation to help you navigate. You might wander to Piazza del Popolo (People’s Square) to browse artisanal boutiques offering hand-woven linens, filet lace, and colorful ceramics. Or, pay a visit to the Church of St. Anthony, which mirrors the architectural style of the surrounding trulli. For a sweet finish, stop by Pasticceria Martinucci for a delicious gelato.

Later this afternoon, continue your journey to Ostuni, known as the “White City” for its dazzling whitewashed buildings. After settling into your hotel, join your leaders for a stroll through this hilltop town with sweeping views of the Adriatic coast. Admire landmarks like the impressive 15th-century Ostuni Cathedral, the Bishop’s Palace, and other historic palazzi—elegant reminders of the noble families who once called this town home.

Afterward, enjoy an aperitivo or browse the local shops for beautifully crafted ceramics. For dinner on your own, consider one of your leaders’ favorite osterias along the route. Alternatively, unwind at the hotel’s spa and dine at the hotel’s acclaimed bistrot for a relaxing evening in.

Included Meals: Breakfast, Lunch

5 miles, easy

This morning, take time to enjoy a leisurely breakfast. After bidding farewell to Ostuni, you journey south toward the medieval port town of Otranto, where you’ll be staying for the next few nights. Along the way, you’ll stop near Uggiano la Chiesa at a peaceful estate nestled among olive groves and Mediterranean macchia (scrubland).

This special property is the award-winning passion project, and Country Walkers’ Responsible Travel Initiative in the region, of sisters Giulia and Lucia Starace, who are preserving traditional textile arts for future generations. Here, a dedicated team of weavers teaches local children about age-old craftsmanship and the values of responsible culture. Country Walkers is proud to support the Le Costantine Foundation with a donation made on behalf of each guest on this tour. On arrival, stroll through a landscape dotted with myrtle, holm oaks, wild orchids, and one of the region’s oldest beehives. At the heart of the estate, enjoy a demonstration at the cooperative weaving studio, which recently contributed to the cruise collection of Parisian fashion house Dior. Afterwards, savor a delicious lunch on the grounds of this inspiring property.

In the afternoon, set off on foot for an easy walk back in time to the Bronze Age. Your destination is Italy’s megalithic garden in and around nearby Giurdignano, home to more than 25 menhirs and dolmens—mysterious standing stones that offer a fascinating glimpse into prehistoric life.

Continue your exploration with a visit to a 16th-century underground olive mill, and the evocative crypt of San Salvatore, dating back to the 8th century and adorned with remarkably well-preserved 13th-century frescoes.

Your walk concludes at a stunning whitewashed masseria just outside Otranto. On arrival, enjoy a sommelier-guided wine tasting paired with traditional Salentino snacks. Dinner is on your own this evening; a complimentary shuttle into town is available, or you may choose to dine at the masseria’s excellent on-site restaurant.

Included Meals: Breakfast, Lunch

4.5 miles, easy to moderate, 670-ft. elevation gain and 2.5 miles, easy to moderate

After another hearty breakfast, you set out for Otranto’s harbor and the trailhead for today’s exploration. Italy’s easternmost city, Otranto enjoys a striking location on the Strait of Otranto, where the Adriatic and Ionian seas meet. Greeks, Romans, Byzantines, Normans, and Aragonese have all laid claim to this strategic port, leaving behind a rich and layered history.

This morning’s walking route traces the rugged Adriatic shoreline, passing dramatic coves and sea-carved caves. Along the way, you’ll encounter the aromatic macchia—the hardy Mediterranean scrubland—and a series of ancient watchtowers, once vital to defending the coast from Turkish incursions. The stark, rocky landscape paired with the shimmering sea eventually leads you to a striking, abandoned bauxite quarry. Once a source of stone shipped as far as Venice for building the Republic’s grandeur, today it’s a surreal basin with crimson walls surrounding a bright, still lake—hence its nickname, Red Lake.

From here, continue on toward the Punta Palascia lighthouse, Italy’s easternmost point. After visiting the lighthouse, travel by minibus to a welcoming, family-run agriturismo, where a local cheesemaker invites you in for a demonstration and a light lunch featuring regional specialties—antipasti salentini, fresh cheeses, and homemade bread.

Later, travel on foot or by minibus to Porto Badisco, a picturesque bay where clear turquoise waters and a white-sand seabed invite you for a refreshing swim. According to Virgil, this was the site where Aeneas first landed after fleeing the fall of Troy.

Upon returning to the hotel, enjoy some time to unwind—perhaps poolside or with a relaxing massage—before heading to a nearby masseria for dinner. This warm, authentic experience is sure to be a highlight of your adventure.

Included Meals: Breakfast, Lunch, Dinner

2 miles, easy to moderate and 1-2 miles, easy

On today’s walk, you’ll trace routes of historical and environmental significance along Puglia’s southernmost coast, through the Parco Naturale Regionale Costa Otranto–Santa Maria di Leuca e Bosco di Tricase. After enjoying a hearty breakfast, you’ll travel to the outskirts of Corsano to begin your uniquely rewarding day.

You start along a rocky, single-track coastal trail, which may be dotted with spring wildflowers and infused with the fragrant scent of Mediterranean macchia. Along the way, you’ll pass typical Salento pajare—dry-stone structures similar to the trulli of Alberobello. These may have originally served as temporary shelters, agricultural storehouses, or dwellings for farm workers. Your path, or tratturo as it’s locally known, follows the ancient Via del Sale (“Salt Route” or “Way”), once used by workers to transport salt harvested from sea water and dried in large cliffside tanks. These laborers were nicknamed Carcagni Tosti (“hard heels”) for their barefoot treks along the rocky coast.

Your trail culminates at Torre Specchia Ruggeri, an ancient watchtower built in 1568 to defend the coast from Saracen invasions. From here, continue by minibus to Santa Maria di Leuca, often referred to as the white pearl of Puglia.

This is the point where the Adriatic and Ionian seas swirl together, and the southernmost tip of the Via Francigena. This ancient pilgrimage route—whose name means “the road from France”—stretches from Canterbury to Rome and continues through Puglia, where pilgrims once sailed onward to the Holy Land. Over the centuries, traders, pirates, and invaders have all left their mark on the history and culture of Capo di Leuca.

Upon arrival, visit the impressive Basilica di Finibus Terrae, perched above the town’s harbor. Its name translates to “basilica at the end of the earth,” a fitting title for this windswept outpost at the edge of the Roman Empire. Your trip leaders will also offer an optional walk along the seaside promenade, highlighting local restaurants for lunch on your own. Later, return to your masseria for time to relax before dinner.

For your final dinner together, gather at the hotel’s al fresco restaurant, where you’ll be welcomed with a glass of sparkling prosecco. Settle in for a memorable meal that celebrates the seasonal bounty of the region. You might savor creamy troccoli pasta with cuttlefish and black chickpea cream, or risotto with Gallipoli’s violet shrimp, pistachios, and pesto—perfectly paired with a glass (or two) of local vino. It’s the ideal way to toast your journey through the beauty and magic of Basilicata and Puglia.

Included Meals: Breakfast, Dinner

Departing shortly after breakfast, you’ll stop in the coastal port of Otranto for an hour-long walking tour with your leaders. This striking seaside town is known for its spectacular waterfront and rich medieval history. A highlight is the Otranto Cathedral, home to an extraordinary 8,611-square-foot mosaic depicting the Tree of Life, crafted by a monk in 1163.

Following the tour, enjoy free time to explore the town’s artisanal shops, where you’ll find clay whistles, woven baskets, hand-dyed fabrics, and traditional ceramics.

Your journey concludes in Lecce, often called the Florence of the South for its remarkable Baroque architecture. Bid farewell to your Country Walkers leaders at the post-tour hotel in Lecce by 12:30 p.m.

Included Meals: Breakfast