Portugal: Sintra, Óbidos & the Coast

Meet in Lisbon. Parques de Sintra forest walk; 4 miles, easy to moderate, 500-ft. elevation gain and 1,000-ft. elevation loss

Your guide(s) will meet you at 8:30 a.m. at the Hotel Sofitel Lisbon Liberdade Please be dressed in hiking shoes for the walk in the Parques de Sintra (Sintra Forest).

Following a short introductory meeting you and your fellow adventurers travel 45 minutes to Cabo da Roca, the westernmost point of Europe, believed to be the end of the world until the 14th century. After a brief stop to admire this rugged coastline, continue (20 minutes) to the cool green hills of the Serra de Sintra, a stunning coastal mountain range. Nestled among the northern slopes, forested ravines and burbling springs, the pastel-hued buildings of Sintra evoke images from a colorful storybook. It’s easy to understand why this scenic corner of Portugal was a favored summer retreat for kings. The stunning palaces they’ve left behind dominate this luxuriant landscape. Superb for exploring on foot, the historic area is rich in sublime scenery. Forests of eucalyptus, acacia and pine stretch to rocky outcrops with distant ocean views. Scattered among the opulent royal palaces is an impressive array of cultural and historic sights, from stately manses and royal hunting lodges to castles clinging to hillsides. Walking through this fairy tale canvas is pure pleasure; it even inspired Lord Byron to proclaim it a “glorious Eden” and to pen his epic poem Childe Harold’s Pilgrimage.

Your trail leads into the Old Town, a UNESCO World Heritage Site, where you stop for a lunch of local specialties, enjoyed on a scenic outdoor terrace. The town’s remarkable heart: the Palace of Sintra, lies just below. Its odd milk-bottle shaped chimneys set it apart, but the rest, as you discover while touring it, is grace personified: a blend of Gothic, Moorish and Manueline styles that have been added and tweaked since the 14th century, when João I first built his retreat. The sprawling complex remained home to the Portuguese royal family until the 1880s.

Later, a two-hour drive delivers you to the rural hamlet of Alvados, a pocket of Portugal so remote that you won’t find it in typical guide books. Amid the dry-stone walls and ancient oak and olive trees, life has not changed much over the centuries, giving you a glimpse of Portugal’s authentic side. Upon arrival at your lodge, settle in and gather this evening for a welcome dinner featuring the bounty of the season. Numerous types of fish are found on most any Portuguese menu, from cod to red mullet. Beef, chicken, and pork are staples in agricultural provinces. No matter what’s on your plate, it is sure to have a Mediterranean influence, perhaps prepared with garlic, olive oil, and even saffron. This evening, your meal may include roasted cod enhanced with a medley of fresh vegetables from the property’s garden, perhaps finished by a chocolate lava cake and accompanied by a smooth Alentejo red or crisp white wine.

Parque Natural das Serras de Aire e Candeeiros; 5.5-7.5 miles, easy to moderate, maximum of 1,100-ft elevation gain and loss

The gentle rolling slopes of Alvados are truly captivating. Hills of lichen-covered limestone overlook the sinewy curves of emerald valleys and majestic rises marked by the striations of millennia. As you walk this mountain terrain, the play of light dazzles, setting ravines ablaze in yellows, ambers, and golds. Before embarking on the trail, enjoy the vistas as you sip your morning café com leite (coffee with steamed milk) and savor a breakfast of homemade preserves and breads, cheeses and cured meats. Fueled for the morning, you depart directly from the hotel to trek up to a scenic plateau, taking in expansive views of distant villages and hills within and beyond the Alvados Valley. A distinct geological feature of this region are the spectacular panoramas of wide polje, or karst fields. (A less strenuous option is to take a ride up to the ridge, where you meet the group for lunch, the traverse, and the descent.) Reward yourself with a delicious picnic lunch prepared by your hotel kitchen. Refreshed and renewed, you loop back to your lodge, descending into ancient olive tree groves and stretches of sylvan Mediterranean forest.

This afternoon, you may choose to indulge in the services of the spa, soaking in a warm pool, sinking in to a calming massage, or swimming in the outdoor pool surrounded by limestone hills.

Later, reconvene in the kitchen for a special cooking lesson. To whet your appetite for modern Portuguese gastronomy, get started with samples of local cheeses and olive oil before strolling through the herb garden, wine glass in hand, to source ingredients for your dinner menu. If you’d rather let someone else—such as the chef and your fellow travelers!—work in the kitchen, relax with a cocktail: The Honesty Bar is stocked with indigenous botanicals to mix into your gin and tonic. Drink in hand, your only job will be to take in the scenery and enjoy the unique aromas and flavors of Alvados while the bread bakes.

Parque Natural das Serras de Aire e Candeeiros to Óbidos; 4.2 miles, easy

If you wish, begin your day early with an optional hike into the Fórnea Valley. Your path crosses a valley on a dirt road, passing lush vegetation and olive groves. The destination of your walk, through low shrub aromatic with lavender and rosemary, is Fórnea, a huge, U-shaped natural amphitheater created from the erosion of karst stone. Its walls soar to 672 feet! Along your trail, keep watch for rich bird life, including the short-toed and Bonelli’s eagle and the red-billed chough, a crow species with a red beak and red feet.

Later, transfer to the historic town of Batalha. The town’s literal translation is “battle,” a fitting name, perhaps, for it was founded by King D. João I to commemorate the Portuguese triumph over the Castilians at the 1385 Battle of Aljubarrota. Its centerpiece, a breathtaking Dominican monastery, is one of Portugal’s most important Gothic sites, with influence from the Manueline style. There’ll be time here to admire the stained-glass windows, some dating to 1514, and gaze up at the soaring vaulted nave. Wander through town, where you may stop at one of the charming cafes for an independent lunch. After, continue to the beautiful whitewashed town of Óbidos, where you settle into historic accommodations just below the converted hilltop castle.

Picture-postcard Óbidos enchants with its gleaming white facades and terra cotta roofs, all tucked within a serpentine 14th-century crenellated wall and sentry-like watchtowers that crawl over hillsides. In 1282, King Dinis offered Óbidos to Queen Isabel of Aragon on their wedding day. Another famous marriage—between the future King Afonso V and his cousin Isabel, aged 10 and 8, respectively—took place in 1441 at the town’s Santa Maria church. At the time, Óbidos’s riverside locale close to the Atlantic made it a busy and prosperous port. But the river silted up in the 1500s. The town has since been restored and is one of Portugal’s most beautiful gems. Early evening, step out with your guide(s) for a short stroll through the labyrinth of cobbled streets.

Dine in the elegant restaurant within the castle walls, sampling a menu that is a worthy complement to your historic accommodations. Seasonal produce and locally-sourced products are used in preparing traditional yet delicate recipes, from sea bream ceviche and cod, octopus, and cuttlefish to a traditional tartlet infused with egg yolk, sugar and sweet pumpkin.

Parque Natural do Costa Vicentina via Setúbal Peninsula/Parque Natural da Arrábida; 5 miles, easy to moderate, 656-ft elevation gain

Rise early and step out your hotel’s front door to witness Óbidos as it shakes off its slumber. Crowd-free streets and the hush of morning cast a magical air on this charming town that seems at its most authentic and pure at this hour of the day. After breakfast, transfer 90 minutes to the Setúbal Peninsula, located within the Parque Natural da Arrábida, dramatically situated between emerald-green hills and the blue Atlantic. Set off on a walk along the scenic trails of this magnificent region that enjoys a Mediterranean-like climate. As you trace the rugged, chalky coast, admire soft-sand crescent beaches lapped by white roiling surf. Refuel during a splendid midday meal at a luxurious wine-producing estate that transforms its grapes into the peninsula’s renowned vintages. During lunch, you of course have the chance to sample a glass or two and perhaps also try the farm’s popular Azeitão cheese.

Enjoy a stroll around the property before traveling south two hours to the Parque Natural do Costa Vicentina in the southwestern region of Baixo Alentejo. Soaring cliffs blanketed with pine trees and skirted by pristine beaches make this one of Europe’s best preserved coastlines. A rich biodiversity has emerged in this undisturbed corner of Portugal. During the next two days as you walk the Rota Vicentina, or Fishermen’s Trail, a stunning variety of vegetation, more than 20 species of birds, and other coastal fauna accompany you, as does a rich history: This long-distance path was long used by fishermen and locals to get to the best fishing areas and most secluded beaches.

After this very full day, settle in for the next three nights and the first of three delicious meals featuring the bounty of the nearby sea.

Parque Natural do Costa Vicentina; 5-7.5 miles, easy

Today’s more leisurely day begins with a hearty breakfast of eggs, hams and cheeses, and mini pastéis de nata, Portugal’s ubiquitous custard tarts. After, depart directly on foot to the trailhead to begin a breathtaking few hours of coastal walking over high ledges and through brush kissed by salty sea air. This is seaside Portugal at its most wild and you’re sure to marvel at its unspoiled drama at every turn. The Fishermen’s Trail leads you to high dramatic cliffs on a path of red-hued earth and sandstone. As you walk, keep watch for the many species of bird that nest here: jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon, are among them. Storks, too, have created a unique habitat here; this is the only place in the world where they nest on cliffs. Take your time and absorb the magnificent beauty at an easy pace, lingering at scenic outlooks or following a path down to an inviting beach. You reach your final destination, the Cabo Sardão lighthouse, from where you shuttle to a nearby restaurant for lunch.

This afternoon, you might embark on an optional coastal walk with your guides or return to the hotel via a short transfer to relax with a good book poolside or explore more of this bucolic area on your own. Later, gather with your fellow walkers for a transfer to the nearby town of Zambujeira, a lovely clifftop village overlooking the ocean. Enjoy dinner on your own this evening as the sun sets the sky ablaze while disappearing behind the Atlantic.

Parque Natural do Costa Vicentina: Praia de Odeceixe to Zambujeira do Mar; 8.7 miles, easy to moderate, elevation gain of 1,200 ft and loss of 1,100 ft. Or Praia da Azenha do Mar to Zambujeira do Mar; 6 miles, easy to moderate, same elevation gain/loss or Praia da Amalia to Zambujeira do Mar; 4.2 miles, easy to moderate, same elevation gain/loss

After another hearty breakfast, transfer to Ponta em Branco, the White Summit—so named for the distinct color of its sediment. From this dramatic perch, gaze upon Praia de Odeceixe. One of the area’s most beautiful beaches, it strikes a stunning pose against the backdrop of Mount Fóia, the highest point of the Serra de Monchique range. Nearby, the scenic Seix stream delineates the Alentejo and the Algarve regions of Portugal.

Today’s walk is more undulating as you ascend and descend from and to beaches of unimaginable beauty. Follow packed-dirt trails through pine, evergreen, oak, and eucalyptus forest and deep-sand paths through heath landscapes that hug the shore. It promises to be an invigorating day of inspiring vistas with ample surprises, perhaps even a surfer or two at Praia do Carvalhal. From Praia Odeceixe, continue walking the Fishermen’s Trail cliffs, formed over millennia by compressed sand, clay, and ash that once lay at the bottom of an ancient ocean. Gold-sand beaches caressed by white cresting waves unfold below. Locals use the hanging ropes you might see to access the sands and harvest shellfish.

Pause for a break and a cold drink at an outdoor restaurant in Azenha do Mar, which rests on an arresting natural fishing harbor encircled by towering rocks. Those preferring a slightly shorter walk today will begin here instead of at Praia Odeceixe. As you continue, you might encounter an endemic rabbit species from which all other rabbits are believed to have descended. Follow more scenic footpaths to Praia da Amalia, difficult to access except by foot. This beautiful beach, also the starting point for the day’s shortest walk option, was named for the house perched above, built by the beloved fado singer, Amalia Rodrigues. Renew yourself with a swim in the cool surf or wade in to refresh your feet and legs. After time here, continue to more magnificent vistas. Your walk concludes in Zambujeira do Mar. After time to linger in a café or peruse the small shops, return to your hotel, where there is time to relax before indulging in a festive dinner celebrating the week’s adventures.

Meet in Lisbon. Parques de Sintra forest walk; 4 miles, easy to moderate, 500-ft. elevation gain and 1,000-ft. elevation loss

Awakening refreshed, you enjoy an included breakfast at your hotel before meeting your group at 8:30 a.m. at the Hotel Sofitel Lisbon Liberdade in Lisbon. Your guide(s) will be wearing a Country Walkers shirt. After a brief introduction to the group, your adventure begins. Please be dressed in hiking shoes for the walk in the Sintra Forest.

Following a short introductory meeting you and your fellow adventurers travel 45 minutes to Cabo da Roca, the westernmost point of Europe, believed to be the end of the world until the 14th century. After a brief stop to admire this rugged coastline, continue (20 minutes) to the cool green hills of the Serra de Sintra, a stunning coastal mountain range. Nestled among the northern slopes, forested ravines and bubbling springs, the pastel-hued buildings of Sintra evoke images from a colorful storybook. It’s easy to understand why this scenic corner of Portugal was a favored summer retreat for kings. The stunning palaces they’ve left behind dominate this luxuriant landscape. Superb for exploring on foot, the historic area is rich in sublime scenery. Forests of eucalyptus, acacia, and pine stretch to rocky outcrops with distant ocean views. Scattered among the opulent royal palaces is an impressive array of cultural and historic sights, from stately manses and royal hunting lodges to castles clinging to hillsides. Walking through this fairy tale canvas is pure pleasure; it even inspired Lord Byron to proclaim it a “glorious Eden” and to pen his epic poem Childe Harold’s Pilgrimage.

Your trail leads into the Old Town, a UNESCO World Heritage site, where you stop for a lunch of local specialties, enjoyed on a scenic outdoor terrace. The town’s remarkable heart: the Palace of Sintra, lies just below. Its odd milk bottle-shaped chimneys set it apart, but the rest, as you discover while touring it, is grace personified: a blend of Gothic, Moorish, and Manueline styles that have been added and tweaked since the 14th century, when João I first built his retreat. The sprawling complex remained home to the Portuguese royal family until the 1880s.

Later, a two-hour drive delivers you to the rural hamlet of Alvados, a pocket of Portugal so remote that you won’t find it in typical guide books. Amid the dry-stone walls and ancient oak and olive trees, life has not changed much over the centuries, giving you a glimpse of Portugal’s authentic side. Upon arrival at your lodge, settle in and gather this evening for a welcome dinner featuring the bounty of the season. Numerous types of fish are found on most any Portuguese menu, from cod to red mullet. Beef, chicken, and pork are staples in agricultural provinces. No matter what’s on your plate, it is sure to have a Mediterranean influence, perhaps prepared with garlic, olive oil, and even saffron. This evening, your meal may include roasted cod enhanced with a medley of fresh vegetables from the property’s garden, perhaps finished by a chocolate lava cake and accompanied by a smooth Alentejo red or crisp white wine.

Accommodation: Cooking and Nature Hotel, Alvados, Portugal

Parque Natural das Serras de Aire e Candeeiros; 5.5-7.5 miles, easy to moderate, maximum of 1,100-ft. elevation gain and loss

The gentle rolling slopes of Alvados are truly captivating. Hills of lichen-covered limestone overlook the sinewy curves of emerald valleys and majestic rises marked by the striations of millennia. As you walk this mountain terrain, the play of light dazzles, setting ravines ablaze in yellows, ambers, and golds. Before embarking on the trail, enjoy the vistas as you sip your morning café com leite (coffee with steamed milk) and savor a breakfast of homemade preserves and breads, cheeses and cured meats. Fueled for the morning, you depart directly from the hotel to trek up to a scenic plateau, taking in expansive views of distant villages and hills within and beyond the Alvados Valley. A distinct geological feature of this region are the spectacular panoramas of wide polje, or karst fields. (A less strenuous option is to take a ride up to the ridge, where you meet the group for lunch, the traverse, and the descent.) Reward yourself with a delicious picnic lunch prepared by your hotel kitchen. Refreshed and renewed, you loop back to your lodge, descending into ancient olive tree groves and stretches of sylvan Mediterranean forest.

This afternoon, you may choose to indulge in the services of the spa, soaking in a warm pool, sinking in to a calming massage, or swimming in the outdoor pool surrounded by limestone hills.

Later, reconvene in the kitchen for a special cooking lesson. To whet your appetite for modern Portuguese gastronomy, get started with samples of local cheeses and olive oil before strolling through the herb garden, wine glass in hand, to source ingredients for your dinner menu. If you’d rather let someone else—such as the chef and your fellow travelers!—work in the kitchen, relax with a cocktail: The Honesty Bar is stocked with indigenous botanicals to mix into your gin and tonic. Drink in hand, your only job will be to take in the scenery and enjoy the unique aromas and flavors of Alvados while the bread bakes.

Accommodation: Cooking and Nature Hotel

Parque Natural das Serras de Aire e Candeeiros to Óbidos; 4.2 miles, easy

If you wish, begin your day early with an optional hike into the Fórnea Valley. Your path crosses a valley on a dirt road, passing lush vegetation and olive groves. The destination of your walk, through low shrub aromatic with lavender and rosemary, is Fórnea, a huge, U-shaped natural amphitheater created from the erosion of karst stone. Its walls soar to 672 feet! Along your trail, keep watch for rich bird life, including the short-toed and Bonelli’s eagle and the red-billed chough, a crow species with a red beak and red feet.

Later, transfer to the historic town of Batalha. The town’s literal translation is “battle,” a fitting name, perhaps, for it was founded by King D. João I to commemorate the Portuguese triumph over the Castilians at the 1385 Battle of Aljubarrota. Its centerpiece, a breathtaking Dominican monastery, is one of Portugal’s most important Gothic sites, with influence from the Manueline style. There’ll be time here to admire the stained-glass windows, some dating to 1514, and gaze up at the soaring vaulted nave. Wander through town, where you may stop at one of the charming cafes for an independent lunch. Continue to the beautiful whitewashed town of Óbidos, where you wander through town, stopping at one of the many charming cafés for an independent lunch. Later, settle into historic accommodations just below the converted hilltop castle.

Picture-postcard Óbidos enchants with its gleaming white facades and terra-cotta roofs, all tucked within a serpentine 14th-century crenellated wall and sentry-like watchtowers that crawl over hillsides. In 1282, King Dinis offered Óbidos to Queen Isabel of Aragon on their wedding day. Another famous marriage—between the future King Afonso V and his cousin Isabel, aged 10 and 8, respectively—took place in 1441 at the town’s Santa Maria church. At the time, Óbidos’s riverside locale close to the Atlantic made it a busy and prosperous port. But the river silted up in the 1500s. The town has since been restored and is one of Portugal’s most beautiful gems. Early evening, step out with your guide(s) for a short stroll through the labyrinth of cobbled streets.

Dine in the elegant restaurant within the castle walls, sampling a menu that is a worthy complement to your historic accommodations. Seasonal produce and locally sourced products are used in preparing traditional yet delicate recipes, from sea bream ceviche and cod, octopus, and cuttlefish to a traditional tartlet infused with egg yolk, sugar, and sweet pumpkin.

Accommodation: Pousada da Vila de Óbidos, Óbidos

Parque Natural do Costa Vicentina via Setúbal Peninsula/Parque Natural da Arrábida; 5 miles, easy to moderate, 656-ft. elevation gain

Rise early and step out your hotel’s front door to witness Óbidos as it shakes off its slumber. Crowd-free streets and the hush of morning cast a magical air on this charming town that seems at its most authentic and pure at this hour of the day. After breakfast, transfer 90 minutes to the Setúbal Peninsula, located within the Parque Natural da Arrábida, dramatically situated between emerald-green hills and the blue Atlantic. Set off on a walk along the scenic trails of this magnificent region that enjoys a Mediterranean-like climate. As you trace the rugged, chalky coast, admire soft-sand crescent beaches lapped by white roiling surf. Refuel during a splendid midday meal at a luxurious wine-producing estate that transforms its grapes into the peninsula’s renowned vintages. During lunch, you of course have the chance to sample a glass or two and perhaps also try the farm’s popular Azeitão cheese.

Enjoy a stroll around the property before traveling south two hours to the Parque Natural do Costa Vicentina in the southwestern region of Baixo Alentejo. Soaring cliffs blanketed with pine trees and skirted by pristine beaches make this one of Europe’s best preserved coastlines. A rich biodiversity has emerged in this undisturbed corner of Portugal. During the next two days as you walk the Rota Vicentina, or Fishermen’s Trail, a stunning variety of vegetation, more than 20 species of birds, and other coastal fauna accompany you, as does a rich history: This long-distance path was long used by fishermen and locals to get to the best fishing areas and most secluded beaches.

After this very full day, settle in for the next three nights and the first of three delicious meals featuring the bounty of the nearby sea.

Accommodation: Herdade do Touril

Parque Natural do Costa Vicentina; 5-10 miles, easy to moderate

Today’s more leisurely day begins with a hearty breakfast of eggs, hams and cheeses, and mini pastéis de nata, Portugal’s ubiquitous custard tarts. After, depart directly on foot to the trailhead to begin a breathtaking few hours of coastal walking over high ledges and through brush kissed by salty sea air. This is seaside Portugal at its most wild and you’re sure to marvel at its unspoiled drama at every turn. The Fishermen’s Trail leads you to high, dramatic cliffs on a path of red-hued earth and sandstone. As you walk, keep watch for the many species of bird that nest here: jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon, are among them. Storks, too, have created a unique habitat here; this is the only place in the world where they nest on cliffs. Take your time and absorb the magnificent beauty at an easy pace, lingering at scenic outlooks or following a path down to an inviting beach. You reach the Cabo Sardão lighthouse midday, and stop to refuel at a nearby restaurant for lunch.

This afternoon, you might embark on an optional coastal walk to Praia do Almograve with your guides or return to the hotel via a short transfer to relax with a good book poolside or explore more of this bucolic area on your own. Later, gather with your fellow walkers for a transfer to the nearby town of Zambujeira, a lovely clifftop village overlooking the ocean. Enjoy dinner on your own this evening as the sun sets the sky ablaze while disappearing behind the Atlantic.

Accommodation: Herdade do Touril

Parque Natural do Costa Vicentina: Praia de Odeceixe to Zambujeira do Mar; 9 miles, easy to moderate (with challenging sections), elevation gain of 1,200 ft. and loss of 1,100 ft. or Praia da Azenha do Mar to Zambujeira do Mar; 6 miles, easy to moderate (with challenging sections), same elevation gain/loss or Praia da Amalia to Zambujeira do Mar; 4 miles, easy to moderate, same elevation gain/loss

After another hearty breakfast, transfer to Ponta em Branco, the White Summit—so named for the distinct color of its sediment. From this dramatic perch, gaze upon Praia de Odeceixe. One of the area’s most beautiful beaches, it strikes a stunning pose against the backdrop of Mount Fóia, the highest point of the Serra de Monchique range. Nearby, the scenic Seix stream delineates the Alentejo and the Algarve regions of Portugal.

Today’s walk is more undulating as you ascend and descend from and to beaches of unimaginable beauty. Follow packed-dirt trails through pine, evergreen, oak, and eucalyptus forest and deep-sand paths through heath landscapes that hug the shore. It promises to be an invigorating day of inspiring vistas with ample surprises, perhaps even a surfer or two at Praia do Carvalhal. From Praia Odeceixe, continue walking the Fishermen’s Trail cliffs, formed over millennia by compressed sand, clay, and ash that once lay at the bottom of an ancient ocean. Gold-sand beaches caressed by white cresting waves unfold below. Locals use the hanging ropes you might see to access the sands and harvest shellfish.

Pause for a break and a cold drink at an outdoor restaurant in Azenha do Mar, which rests on an arresting natural fishing harbor encircled by towering rocks. Those preferring a slightly shorter walk today will begin here instead of at Praia Odeceixe. As you continue, you might encounter an endemic rabbit species from which all other rabbits are believed to have descended. Follow more scenic footpaths to Praia da Amalia, difficult to access except by foot. This beautiful beach, also the starting point for the day’s shortest walk option, was named for the house perched above, built by the beloved fado singer, Amalia Rodrigues. Renew yourself with a swim in the cool surf or wade in to refresh your feet and legs. After time here, continue to more magnificent vistas. Your walk concludes in Zambujeira do Mar. After time to linger in a café or peruse the small shops, return to your hotel, where there is time to relax before indulging in a festive dinner celebrating the week’s adventures.

Accommodation: Herdade do Touril

After breakfast, you transfer 2.5 hours to Lisbon, where you may continue your exploration on your own or depart for onward travels.

Meet in Lisbon. Parques de Sintra forest walk; 4 miles, easy to moderate, 500-ft. elevation gain and 1,000-ft. elevation loss

Following a short introductory meeting you and your fellow adventurers travel 45 minutes to Cabo da Roca, the westernmost point of Europe, believed to be the end of the world until the 14th century. After a brief stop to admire this rugged coastline, continue (20 minutes) to the cool green hills of the Serra de Sintra, a stunning coastal mountain range. Nestled among the northern slopes, forested ravines and burbling springs, the pastel-hued buildings of Sintra evoke images from a colorful storybook. It’s easy to understand why this scenic corner of Portugal was a favored summer retreat for kings. The stunning palaces they’ve left behind dominate this luxuriant landscape. Superb for exploring on foot, the historic area is rich in sublime scenery. Forests of eucalyptus, acacia and pine stretch to rocky outcrops with distant ocean views. Scattered among the opulent royal palaces is an impressive array of cultural and historic sights, from stately manses and royal hunting lodges to castles clinging to hillsides. Walking through this fairy tale canvas is pure pleasure; it even inspired Lord Byron to proclaim it a “glorious Eden” and to pen his epic poem Childe Harold’s Pilgrimage.

Your trail leads into the Old Town, a UNESCO World Heritage Site, where you stop for a lunch of local specialties, enjoyed on a scenic outdoor terrace. The town’s remarkable heart: the Palace of Sintra, lies just below. Its odd milk-bottle shaped chimneys set it apart, but the rest, as you discover while touring it, is grace personified: a blend of Gothic, Moorish and Manueline styles that have been added and tweaked since the 14th century, when João I first built his retreat. The sprawling complex remained home to the Portuguese royal family until the 1880s.

Later, a two-hour drive delivers you to the rural hamlet of Alvados, a pocket of Portugal so remote that you won’t find it in typical guide books. Amid the dry-stone walls and ancient oak and olive trees, life has not changed much over the centuries, giving you a glimpse of Portugal’s authentic side. Upon arrival at your lodge, settle in and gather this evening for a welcome dinner featuring the bounty of the season. Numerous types of fish are found on most any Portuguese menu, from cod to red mullet. Beef, chicken, and pork are staples in agricultural provinces. No matter what’s on your plate, it is sure to have a Mediterranean influence, perhaps prepared with garlic, olive oil, and even saffron. This evening, your meal may include roasted cod enhanced with a medley of fresh vegetables from the property’s garden, perhaps finished by a chocolate lava cake and accompanied by a smooth Alentejo red or crisp white wine.

Parque Natural das Serras de Aire e Candeeiros; 5.5-7.5 miles, easy to moderate, maximum of 1,100-ft elevation gain and loss

The gentle rolling slopes of Alvados are truly captivating. Hills of lichen-covered limestone overlook the sinewy curves of emerald valleys and majestic rises marked by the striations of millennia. As you walk this mountain terrain, the play of light dazzles, setting ravines ablaze in yellows, ambers, and golds. Before embarking on the trail, enjoy the vistas as you sip your morning café com leite (coffee with steamed milk) and savor a breakfast of homemade preserves and breads, cheeses and cured meats. Fueled for the morning, you depart directly from the hotel to trek up to a scenic plateau, taking in expansive views of distant villages and hills within and beyond the Alvados Valley. A distinct geological feature of this region are the spectacular panoramas of wide polje, or karst fields. (A less strenuous option is to take a ride up to the ridge, where you meet the group for lunch, the traverse, and the descent.) Reward yourself with a delicious picnic lunch prepared by your hotel kitchen. Refreshed and renewed, you loop back to your lodge, descending into ancient olive tree groves and stretches of sylvan Mediterranean forest.

This afternoon, you may choose to indulge in the services of the spa, soaking in a warm pool, sinking in to a calming massage, or swimming in the outdoor pool surrounded by limestone hills.

Later, reconvene in the kitchen for a special cooking lesson. To whet your appetite for modern Portuguese gastronomy, get started with samples of local cheeses and olive oil before strolling through the herb garden, wine glass in hand, to source ingredients for your dinner menu. If you’d rather let someone else—such as the chef and your fellow travelers!—work in the kitchen, relax with a cocktail: The Honesty Bar is stocked with indigenous botanicals to mix into your gin and tonic. Drink in hand, your only job will be to take in the scenery and enjoy the unique aromas and flavors of Alvados while the bread bakes.

Parque Natural das Serras de Aire e Candeeiros to Óbidos; 4.2 miles, easy

If you wish, begin your day early with an optional hike into the Fórnea Valley. Your path crosses a valley on a dirt road, passing lush vegetation and olive groves. The destination of your walk, through low shrub aromatic with lavender and rosemary, is Fórnea, a huge, U-shaped natural amphitheater created from the erosion of karst stone. Its walls soar to 672 feet! Along your trail, keep watch for rich bird life, including the short-toed and Bonelli’s eagle and the red-billed chough, a crow species with a red beak and red feet.

Later, transfer to the historic town of Batalha. The town’s literal translation is “battle,” a fitting name, perhaps, for it was founded by King D. João I to commemorate the Portuguese triumph over the Castilians at the 1385 Battle of Aljubarrota. Its centerpiece, a breathtaking Dominican monastery, is one of Portugal’s most important Gothic sites, with influence from the Manueline style. There’ll be time here to admire the stained-glass windows, some dating to 1514, and gaze up at the soaring vaulted nave. Wander through town, where you may stop at one of the charming cafes for an independent lunch. After, continue to the beautiful whitewashed town of Óbidos, where you settle into historic accommodations just below the converted hilltop castle.

Picture-postcard Óbidos enchants with its gleaming white facades and terra cotta roofs, all tucked within a serpentine 14th-century crenellated wall and sentry-like watchtowers that crawl over hillsides. In 1282, King Dinis offered Óbidos to Queen Isabel of Aragon on their wedding day. Another famous marriage—between the future King Afonso V and his cousin Isabel, aged 10 and 8, respectively—took place in 1441 at the town’s Santa Maria church. At the time, Óbidos’s riverside locale close to the Atlantic made it a busy and prosperous port. But the river silted up in the 1500s. The town has since been restored and is one of Portugal’s most beautiful gems. Early evening, step out with your guide(s) for a short stroll through the labyrinth of cobbled streets.

Dine in the elegant restaurant within the castle walls, sampling a menu that is a worthy complement to your historic accommodations. Seasonal produce and locally-sourced products are used in preparing traditional yet delicate recipes, from sea bream ceviche and cod, octopus, and cuttlefish to a traditional tartlet infused with egg yolk, sugar and sweet pumpkin.

Parque Natural do Costa Vicentina via Setúbal Peninsula/Parque Natural da Arrábida; 5 miles, easy to moderate, 656-ft elevation gain

Rise early and step out your hotel’s front door to witness Óbidos as it shakes off its slumber. Crowd-free streets and the hush of morning cast a magical air on this charming town that seems at its most authentic and pure at this hour of the day. After breakfast, transfer 90 minutes to the Setúbal Peninsula, located within the Parque Natural da Arrábida, dramatically situated between emerald-green hills and the blue Atlantic. Set off on a walk along the scenic trails of this magnificent region that enjoys a Mediterranean-like climate. As you trace the rugged, chalky coast, admire soft-sand crescent beaches lapped by white roiling surf. Refuel during a splendid midday meal at a luxurious wine-producing estate that transforms its grapes into the peninsula’s renowned vintages. During lunch, you of course have the chance to sample a glass or two and perhaps also try the farm’s popular Azeitão cheese.

Enjoy a stroll around the property before traveling south two hours to the Parque Natural do Costa Vicentina in the southwestern region of Baixo Alentejo. Soaring cliffs blanketed with pine trees and skirted by pristine beaches make this one of Europe’s best preserved coastlines. A rich biodiversity has emerged in this undisturbed corner of Portugal. During the next two days as you walk the Rota Vicentina, or Fishermen’s Trail, a stunning variety of vegetation, more than 20 species of birds, and other coastal fauna accompany you, as does a rich history: This long-distance path was long used by fishermen and locals to get to the best fishing areas and most secluded beaches.

After this very full day, settle in for the next three nights and the first of three delicious meals featuring the bounty of the nearby sea.

Parque Natural do Costa Vicentina; 5-7.5 miles, easy

Today’s more leisurely day begins with a hearty breakfast of eggs, hams and cheeses, and mini pastéis de nata, Portugal’s ubiquitous custard tarts. After, depart directly on foot to the trailhead to begin a breathtaking few hours of coastal walking over high ledges and through brush kissed by salty sea air. This is seaside Portugal at its most wild and you’re sure to marvel at its unspoiled drama at every turn. The Fishermen’s Trail leads you to high dramatic cliffs on a path of red-hued earth and sandstone. As you walk, keep watch for the many species of bird that nest here: jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon, are among them. Storks, too, have created a unique habitat here; this is the only place in the world where they nest on cliffs. Take your time and absorb the magnificent beauty at an easy pace, lingering at scenic outlooks or following a path down to an inviting beach. You reach your final destination, the Cabo Sardão lighthouse, from where you shuttle to a nearby restaurant for lunch.

This afternoon, you might embark on an optional coastal walk with your guides or return to the hotel via a short transfer to relax with a good book poolside or explore more of this bucolic area on your own. Later, gather with your fellow walkers for a transfer to the nearby town of Zambujeira, a lovely clifftop village overlooking the ocean. Enjoy dinner on your own this evening as the sun sets the sky ablaze while disappearing behind the Atlantic.

Parque Natural do Costa Vicentina: Praia de Odeceixe to Zambujeira do Mar; 8.7 miles, easy to moderate, elevation gain of 1,200 ft and loss of 1,100 ft. Or Praia da Azenha do Mar to Zambujeira do Mar; 6 miles, easy to moderate, same elevation gain/loss or Praia da Amalia to Zambujeira do Mar; 4.2 miles, easy to moderate, same elevation gain/loss

After another hearty breakfast, transfer to Ponta em Branco, the White Summit—so named for the distinct color of its sediment. From this dramatic perch, gaze upon Praia de Odeceixe. One of the area’s most beautiful beaches, it strikes a stunning pose against the backdrop of Mount Fóia, the highest point of the Serra de Monchique range. Nearby, the scenic Seix stream delineates the Alentejo and the Algarve regions of Portugal.

Today’s walk is more undulating as you ascend and descend from and to beaches of unimaginable beauty. Follow packed-dirt trails through pine, evergreen, oak, and eucalyptus forest and deep-sand paths through heath landscapes that hug the shore. It promises to be an invigorating day of inspiring vistas with ample surprises, perhaps even a surfer or two at Praia do Carvalhal. From Praia Odeceixe, continue walking the Fishermen’s Trail cliffs, formed over millennia by compressed sand, clay, and ash that once lay at the bottom of an ancient ocean. Gold-sand beaches caressed by white cresting waves unfold below. Locals use the hanging ropes you might see to access the sands and harvest shellfish.

Pause for a break and a cold drink at an outdoor restaurant in Azenha do Mar, which rests on an arresting natural fishing harbor encircled by towering rocks. Those preferring a slightly shorter walk today will begin here instead of at Praia Odeceixe. As you continue, you might encounter an endemic rabbit species from which all other rabbits are believed to have descended. Follow more scenic footpaths to Praia da Amalia, difficult to access except by foot. This beautiful beach, also the starting point for the day’s shortest walk option, was named for the house perched above, built by the beloved fado singer, Amalia Rodrigues. Renew yourself with a swim in the cool surf or wade in to refresh your feet and legs. After time here, continue to more magnificent vistas. Your walk concludes in Zambujeira do Mar. After time to linger in a café or peruse the small shops, return to your hotel, where there is time to relax before indulging in a festive dinner celebrating the week’s adventures.

After breakfast, you transfer 2.5 hours to Lisbon, where you may continue your exploration on your own or depart for onward travels.

Meet in Lisbon. Parques de Sintra forest walk; 4 miles, easy to moderate, 500-ft. elevation gain and 1,000-ft. elevation loss

Your guide(s) will meet you at 8:30 a.m. at the Hotel Sofitel Lisbon Liberdade in Lisbon and will be wearing a Country Walkers shirt. After a brief introduction to the group, your adventure begins. Please be dressed in hiking shoes for the walk in the Sintra Forest.

Your guide(s) will meet you at 8:30 a.m. at the Hotel Sofitel Lisbon Liberdade. Please be dressed in hiking shoes for the walk in the Parques de Sintra (Sintra Forest).

Following a short introductory meeting you and your fellow adventurers travel 45 minutes to Cabo da Roca, the westernmost point of Europe, believed to be the end of the world until the 14th century. After a brief stop to admire this rugged coastline, continue (20 minutes) to the cool green hills of the Serra de Sintra, a stunning coastal mountain range. Nestled among the northern slopes, forested ravines and bubbling springs, the pastel-hued buildings of Sintra evoke images from a colorful storybook. It’s easy to understand why this scenic corner of Portugal was a favored summer retreat for kings. The stunning palaces they’ve left behind dominate this luxuriant landscape. Superb for exploring on foot, the historic area is rich in sublime scenery. Forests of eucalyptus, acacia, and pine stretch to rocky outcrops with distant ocean views. Scattered among the opulent royal palaces is an impressive array of cultural and historic sights, from stately manses and royal hunting lodges to castles clinging to hillsides. Walking through this fairy tale canvas is pure pleasure; it even inspired Lord Byron to proclaim it a “glorious Eden” and to pen his epic poem Childe Harold’s Pilgrimage.

Your trail leads into the Old Town, a UNESCO World Heritage site, where you stop for a lunch of local specialties, enjoyed on a scenic outdoor terrace. The town’s remarkable heart: the Palace of Sintra, lies just below. Its odd milk bottle-shaped chimneys set it apart, but the rest, as you discover while touring it, is grace personified: a blend of Gothic, Moorish, and Manueline styles that have been added and tweaked since the 14th century, when João I first built his retreat. The sprawling complex remained home to the Portuguese royal family until the 1880s.

Later, a two-hour drive delivers you to the rural hamlet of Alvados, a pocket of Portugal so remote that you won’t find it in typical guide books. Amid the dry-stone walls and ancient oak and olive trees, life has not changed much over the centuries, giving you a glimpse of Portugal’s authentic side. Upon arrival at your lodge, settle in and gather this evening for a welcome dinner featuring the bounty of the season. Numerous types of fish are found on most any Portuguese menu, from cod to red mullet. Beef, chicken, and pork are staples in agricultural provinces. No matter what’s on your plate, it is sure to have a Mediterranean influence, perhaps prepared with garlic, olive oil, and even saffron. This evening, your meal may include roasted cod enhanced with a medley of fresh vegetables from the property’s garden, perhaps finished by a chocolate lava cake and accompanied by a smooth Alentejo red or crisp white wine.

Accommodation: Cooking and Nature Hotel, Alvados, Portugal

Parque Natural das Serras de Aire e Candeeiros; 5.5-7.5 miles, easy to moderate, maximum of 1,100-ft. elevation gain and loss

The gentle rolling slopes of Alvados are truly captivating. Hills of lichen-covered limestone overlook the sinewy curves of emerald valleys and majestic rises marked by the striations of millennia. As you walk this mountain terrain, the play of light dazzles, setting ravines ablaze in yellows, ambers, and golds. Before embarking on the trail, enjoy the vistas as you sip your morning café com leite (coffee with steamed milk) and savor a breakfast of homemade preserves and breads, cheeses and cured meats. Fueled for the morning, you depart directly from the hotel to trek up to a scenic plateau, taking in expansive views of distant villages and hills within and beyond the Alvados Valley. A distinct geological feature of this region are the spectacular panoramas of wide polje, or karst fields. (A less strenuous option is to take a ride up to the ridge, where you meet the group for lunch, the traverse, and the descent.) Reward yourself with a delicious picnic lunch prepared by your hotel kitchen. Refreshed and renewed, you loop back to your lodge, descending into ancient olive tree groves and stretches of sylvan Mediterranean forest.

This afternoon, you may choose to indulge in the services of the spa, soaking in a warm pool, sinking in to a calming massage, or swimming in the outdoor pool surrounded by limestone hills.

Later, reconvene in the kitchen for a special cooking lesson. To whet your appetite for modern Portuguese gastronomy, get started with samples of local cheeses and olive oil before strolling through the herb garden, wine glass in hand, to source ingredients for your dinner menu. If you’d rather let someone else—such as the chef and your fellow travelers!—work in the kitchen, relax with a cocktail: The Honesty Bar is stocked with indigenous botanicals to mix into your gin and tonic. Drink in hand, your only job will be to take in the scenery and enjoy the unique aromas and flavors of Alvados while the bread bakes.

Accommodation: Cooking and Nature Hotel

Parque Natural das Serras de Aire e Candeeiros to Óbidos; 4.2 miles, easy

If you wish, begin your day early with an optional hike into the Fórnea Valley. Your path crosses a valley on a dirt road, passing lush vegetation and olive groves. The destination of your walk, through low shrub aromatic with lavender and rosemary, is Fórnea, a huge, U-shaped natural amphitheater created from the erosion of karst stone. Its walls soar to 672 feet! Along your trail, keep watch for rich bird life, including the short-toed and Bonelli’s eagle and the red-billed chough, a crow species with a red beak and red feet.

Later, transfer to the historic town of Batalha. The town’s literal translation is “battle,” a fitting name, perhaps, for it was founded by King D. João I to commemorate the Portuguese triumph over the Castilians at the 1385 Battle of Aljubarrota. Its centerpiece, a breathtaking Dominican monastery, is one of Portugal’s most important Gothic sites, with influence from the Manueline style. There’ll be time here to admire the stained-glass windows, some dating to 1514, and gaze up at the soaring vaulted nave. Wander through town, where you may stop at one of the charming cafes for an independent lunch. Continue to the beautiful whitewashed town of Óbidos, where you wander through town, stopping at one of the many charming cafés for an independent lunch. Later, settle into historic accommodations just below the converted hilltop castle.

Picture-postcard Óbidos enchants with its gleaming white facades and terra-cotta roofs, all tucked within a serpentine 14th-century crenellated wall and sentry-like watchtowers that crawl over hillsides. In 1282, King Dinis offered Óbidos to Queen Isabel of Aragon on their wedding day. Another famous marriage—between the future King Afonso V and his cousin Isabel, aged 10 and 8, respectively—took place in 1441 at the town’s Santa Maria church. At the time, Óbidos’s riverside locale close to the Atlantic made it a busy and prosperous port. But the river silted up in the 1500s. The town has since been restored and is one of Portugal’s most beautiful gems. Early evening, step out with your guide(s) for a short stroll through the labyrinth of cobbled streets.

Dine in the elegant restaurant within the castle walls, sampling a menu that is a worthy complement to your historic accommodations. Seasonal produce and locally sourced products are used in preparing traditional yet delicate recipes, from sea bream ceviche and cod, octopus, and cuttlefish to a traditional tartlet infused with egg yolk, sugar, and sweet pumpkin.

Accommodation: Pousada da Vila de Óbidos, Óbidos

Parque Natural do Costa Vicentina via Setúbal Peninsula/Parque Natural da Arrábida; 5 miles, easy to moderate, 656-ft. elevation gain

Rise early and step out your hotel’s front door to witness Óbidos as it shakes off its slumber. Crowd-free streets and the hush of morning cast a magical air on this charming town that seems at its most authentic and pure at this hour of the day. After breakfast, transfer 90 minutes to the Setúbal Peninsula, located within the Parque Natural da Arrábida, dramatically situated between emerald-green hills and the blue Atlantic. Set off on a walk along the scenic trails of this magnificent region that enjoys a Mediterranean-like climate. As you trace the rugged, chalky coast, admire soft-sand crescent beaches lapped by white roiling surf. Refuel during a splendid midday meal at a luxurious wine-producing estate that transforms its grapes into the peninsula’s renowned vintages. During lunch, you of course have the chance to sample a glass or two and perhaps also try the farm’s popular Azeitão cheese.

Enjoy a stroll around the property before traveling south two hours to the Parque Natural do Costa Vicentina in the southwestern region of Baixo Alentejo. Soaring cliffs blanketed with pine trees and skirted by pristine beaches make this one of Europe’s best preserved coastlines. A rich biodiversity has emerged in this undisturbed corner of Portugal. During the next two days as you walk the Rota Vicentina, or Fishermen’s Trail, a stunning variety of vegetation, more than 20 species of birds, and other coastal fauna accompany you, as does a rich history: This long-distance path was long used by fishermen and locals to get to the best fishing areas and most secluded beaches.

After this very full day, settle in for the next three nights and the first of three delicious meals featuring the bounty of the nearby sea.

Accommodation: Herdade do Touril

Parque Natural do Costa Vicentina; 5-10 miles, easy to moderate

Today’s more leisurely day begins with a hearty breakfast of eggs, hams and cheeses, and mini pastéis de nata, Portugal’s ubiquitous custard tarts. After, depart directly on foot to the trailhead to begin a breathtaking few hours of coastal walking over high ledges and through brush kissed by salty sea air. This is seaside Portugal at its most wild and you’re sure to marvel at its unspoiled drama at every turn. The Fishermen’s Trail leads you to high, dramatic cliffs on a path of red-hued earth and sandstone. As you walk, keep watch for the many species of bird that nest here: jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon, are among them. Storks, too, have created a unique habitat here; this is the only place in the world where they nest on cliffs. Take your time and absorb the magnificent beauty at an easy pace, lingering at scenic outlooks or following a path down to an inviting beach. You reach the Cabo Sardão lighthouse midday, and stop to refuel at a nearby restaurant for lunch.

This afternoon, you might embark on an optional coastal walk to Praia do Almograve with your guides or return to the hotel via a short transfer to relax with a good book poolside or explore more of this bucolic area on your own. Later, gather with your fellow walkers for a transfer to the nearby town of Zambujeira, a lovely clifftop village overlooking the ocean. Enjoy dinner on your own this evening as the sun sets the sky ablaze while disappearing behind the Atlantic.

Accommodation: Herdade do Touril

Parque Natural do Costa Vicentina: Praia de Odeceixe to Zambujeira do Mar; 9 miles, easy to moderate (with challenging sections), elevation gain of 1,200 ft. and loss of 1,100 ft. or Praia da Azenha do Mar to Zambujeira do Mar; 6 miles, easy to moderate (with challenging sections), same elevation gain/loss or Praia da Amalia to Zambujeira do Mar; 4 miles, easy to moderate, same elevation gain/loss

After another hearty breakfast, transfer to Ponta em Branco, the White Summit—so named for the distinct color of its sediment. From this dramatic perch, gaze upon Praia de Odeceixe. One of the area’s most beautiful beaches, it strikes a stunning pose against the backdrop of Mount Fóia, the highest point of the Serra de Monchique range. Nearby, the scenic Seix stream delineates the Alentejo and the Algarve regions of Portugal.

Today’s walk is more undulating as you ascend and descend from and to beaches of unimaginable beauty. Follow packed-dirt trails through pine, evergreen, oak, and eucalyptus forest and deep-sand paths through heath landscapes that hug the shore. It promises to be an invigorating day of inspiring vistas with ample surprises, perhaps even a surfer or two at Praia do Carvalhal. From Praia Odeceixe, continue walking the Fishermen’s Trail cliffs, formed over millennia by compressed sand, clay, and ash that once lay at the bottom of an ancient ocean. Gold-sand beaches caressed by white cresting waves unfold below. Locals use the hanging ropes you might see to access the sands and harvest shellfish.

Pause for a break and a cold drink at an outdoor restaurant in Azenha do Mar, which rests on an arresting natural fishing harbor encircled by towering rocks. Those preferring a slightly shorter walk today will begin here instead of at Praia Odeceixe. As you continue, you might encounter an endemic rabbit species from which all other rabbits are believed to have descended. Follow more scenic footpaths to Praia da Amalia, difficult to access except by foot. This beautiful beach, also the starting point for the day’s shortest walk option, was named for the house perched above, built by the beloved fado singer, Amalia Rodrigues. Renew yourself with a swim in the cool surf or wade in to refresh your feet and legs. After time here, continue to more magnificent vistas. Your walk concludes in Zambujeira do Mar. After time to linger in a café or peruse the small shops, return to your hotel, where there is time to relax before indulging in a festive dinner celebrating the week’s adventures.

Accommodation: Herdade do Touril

After breakfast, you transfer 2.5 hours to Lisbon, where you may continue your exploration on your own or depart for onward travels.