Portugal: Sintra, Evora & The Coast

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

After enjoying an included breakfast at your hotel, meet your guides and group at 8:30 a.m. in the lobby of the Heritage Avenida Liberdade Hotel in Lisbon. They’ll be wearing Country Walkers shirts. After a brief introduction to the group, your adventure begins. 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, until the 14th century the Cabo da Roca was believed to be the end of the world. 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, Sintra’s pastel-hued buildings 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 spectacular palaces they’ve left behind dominate this luxuriant landscape. Superb for exploring on foot, the historical 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 historical sights, from stately manses and royal hunting lodges to hillside castles. Walking through this fairy tale is pure pleasure; it even inspired Lord Byron, who proclaimed it a “glorious Eden,” to pen his epic poem Childe Harold’s Pilgrimage. 

Your trail leads into Sintra’s Old Town, a UNESCO World Heritage site, where you stop for a lunch of local specialties, enjoyed on a scenic outdoor terrace (weather permitting). The town’s remarkable heart, the Palace of Sintra, lies just below. Though its distinctive, bottle-shaped chimneys may seem odd, the rest, as you discover while touring it, is grace personified. Gothic, Moorish, and Manueline styles have been added and tweaked since the 14th century when João I first built this retreat. This sprawling complex was home to the Portuguese royal family until the 1880s. 

Later, a nearly two-hour drive delivers you to Évora, capital of the Alentejo region, and your base for the next two nights. Your boutique hotel was fashioned out of a palatial house located beside a 16th-century aqueduct within the city walls. Like the town itself, the hotel beautifully blends historical and contemporary styles.  

After time to settle in and refresh, reunite with your fellow travelers and guides, and savor a memorable welcome dinner featuring locally sourced ingredients paired with a glass (or two!) of regional wine.

Included Meals: Breakfast, Lunch, Dinner

Today’s walk in the Alentejo traverses typical Mediterranean landscapes dotted with cypress, pomegranate, fig, and ancient olive trees. You depart from the tiny, rural village of Outeiro and soon reach the first of many dolmens and menhirs scattered across the surrounding plains. The area boasts nearly 150 of these carved-rock monoliths and piled structures. Similar to those found in western Ireland, they date from the third and fourth millennia.

A sustained 30-minute climb along a cobbled path brings you to the picturesque hilltop village of Reguengos de Monsaraz, designated the European Wine Capital in 2015. (Your minibus and driver provide a lift up to the village for those who prefer to skip the climb.) From this vantage point you see a huge, modern dam and the Alqueva Lake on one side, and to the East, the Spanish border. Enjoy lunch at a restaurant of your choice, dining at one of the many restaurants with a scenic outdoor terrace, perhaps. Afterward, there is time to stroll this atmospheric village whose cobbled slate streets with whitewashed houses retain an authentic feel. Pop into artisan studios, and be sure to visit the castle, which now houses a bullring within its walls!

Upon your return to Évora, you embark on a walking tour of this fascinating town with your guides—exploring the city’s historic center, including the ancient Roman Temple of Diana (or Temple of Évora) and the Cathedral of Évora, a massive Gothic structure begun in the 12th century. You also visit the Igreja de São Francisco, which features Gothic and baroque architecture and the skeleton-adorned Chapel of Bones. Once an important city for trading and religious purposes, today, Évora is a vibrant university town. Continue exploring on your own or return to your hotel for a relaxing swim in the pool or treatment at the Spa Aqueduto. This evening, enjoy dinner at a restaurant of your choice. Recommendations are provided by your guides.

Included Meals: Breakfast

Bid farewell to Évora and travel south (two hours) to the Parque Natural do Costa Vicentina in the southwestern region of Baixo (lower) Alentejo. Soaring cliffs blanketed with pine trees skirted by pristine beaches make this one of Europe’s best-preserved coastlines. In this undisturbed corner of Portugal, a rich biodiversity has emerged. During the next few days as you walk the Rota Vicentina, or Fishermen’s Trail, you’ll discover a stunning variety of vegetation, more than 20 species of birds, and other coastal fauna. This historical long-distance path was used by fishermen and locals to get to the best fishing areas and most-secluded beaches.

You reach the town of Cavaleiro and enjoy a midday meal of petiscos (small plates) ranging from local cheese and ham to seafood and rice dishes. You depart on foot 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. Along this section of the Fishermen’s Trail, you’ll make your way from the Cabo Sardão lighthouse 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). 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 paths down to inviting beaches.

You arrive on foot at your hotel—a cattle-breeding working estate run by the same family since 1826. Set on a tranquil 900 acres within view of the Atlantic Ocean, its thoughtful design keeps you connected to the Alentejo’s rural beauty, with outdoor terraces and open spaces that afford breathtaking views. Enjoy a welcome drink as the sun sets the sky ablaze while it disappears behind the Atlantic. Then, make your way to your hotel’s cozy restaurant for a delicious dinner of fresh cod (prepared one of 365 ways!) served with local seasonal vegetables, and paired, of course, with one of the region’s fine wines.

Included Meals: Breakfast, Lunch, Dinner

After another hearty breakfast, drive 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, which 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 Algarve regions of Portugal.

Today’s walk is more undulating (and challenging!) as you ascend and descend to and from 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 you’ll even spot 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. You might see the hanging ropes the locals use 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 scenic footpaths to Praia da Amalia beach, which is difficult to access except by foot. This 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 through more magnificent vistas. Your walk concludes in Zambujeira do Mar. Take time to linger in a café or peruse the small shops, then return to your hotel where you refresh and relax before dinner at a favorite restaurant featuring bounty from the sea.

Included Meals: Breakfast, Lunch, Dinner

After breakfast, you travel north to the Setúbal Peninsula, stopping en route for another walk along the Fishermen’s Trail. Today, you’ll make your way from Cavaleiro to Praia do Almograve, along a dramatic route with contrasting sights—black rock outcrops and vast expanses of golden, shifting sands. As the trail nudges near the edge of the beach, you’ll pass by rock pools teeming with marine life. Further inland, you’ll find the landscape blanketed by “ice” plants with colorful flowers that shimmer in the sunlight as though encased in ice. Approaching the fishing harbor of Porto das Lapas das Pombas, local traditions come to life, as fishermen pull in the catch of the day in a picturesque setting.

Refuel over a lunch of local specialties in the village of Almograve before continuing (via a two-hour minibus drive) to your final destination—a historic pousada overlooking the hills of the Arrábida and the Atlantic. Settle in to your beautifully appointed room and relax on the terrace with an aperitif, or take a stroll around the expansive grounds.

Enjoy dinner on your own at the casual bar or in the elegant restaurant within the hotel, or step out to one of the casual dining options in town.

Included Meals: Breakfast, Lunch

Enjoy a leisurely breakfast, perhaps with a cup of café com leite, a Portuguese coffee-and-milk drink similar to a latte, in the former convent’s cloisters. Then, depart for this morning’s gorgeous walk along the Cabo Espichel, or Espichel Cape. Located on the southwestern tip of the Setúbal Peninsula, you’ll make your way through a primitive landscape of wind-blasted trees and towering cliffs with blue ocean waters glistening below. The peninsula boasts a series of spectacular hiking trails (your guide will choose the best route depending on the weather and trail conditions). Highlights along the way include the Cabo Espichel Lighthouse, the Chapel of Ermida da Memória, and two sets of dinosaur footprint fossils.

Lunch is at the restaurant of your choice in the picturesque fishing port of Sesimbra, nestled at the foothills of the Serra da Arrábida Natural Park. Your guides provide recommendations of where to try a meal of fried cuttlefish or another catch of the day. Then, return to your hotel with a stop en route in Azeitão for a wine tasting (and maybe a sample of the famous local cheese) and the opportunity to explore the town. Stop in at an artisan’s workshop for a closer look at the tile-making or other artisanal crafts and, perhaps, pick up a souvenir. Back at your accommodation, you’ll have time to relax in one of the hotel’s common spaces, a glass of the area’s famous muscatel in hand before gathering for a festive evening celebration to toast the week’s adventures.

Included Meals: Breakfast, Dinner

You depart this morning for Lisbon, Portugal’s vibrant capital, where you bid adeus (farewell) to your guides and travel companions to enjoy an evening on your own and an overnight in the city. The area around your hotel offers ample choices for lunch and dinner on your own.

Included Meals: Breakfast

Your guides will meet you at 8:30 a.m. in the lobby of the Heritage Avenida Liberdade Hotel, Avenida da Liberdade, 28 in Lisbon and will be wearing Country Walkers shirts. After a brief introduction to the group, your adventure begins. 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, until the 14th century the Cabo da Roca was believed to be the end of the world. 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, Sintra’s pastel-hued buildings 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 spectacular palaces they’ve left behind dominate this luxuriant landscape. Superb for exploring on foot, the historical 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 historical sights, from stately manses and royal hunting lodges to hillside castles. Walking through this fairy tale is pure pleasure; it even inspired Lord Byron, who proclaimed it a “glorious Eden,” to pen his epic poem Childe Harold’s Pilgrimage.

Your trail leads into Sintra’s Old Town, a UNESCO World Heritage site, where you stop for a lunch of local specialties, enjoyed on a scenic outdoor terrace (weather permitting). The town’s remarkable heart, the Palace of Sintra, lies just below. Though its distinctive, bottle-shaped chimneys may seem odd, the rest, as you discover while touring it, is grace personified. Gothic, Moorish, and Manueline styles have been added and tweaked since the 14th century when João I first built this retreat. This sprawling complex was home to the Portuguese royal family until the 1880s.

Later, a nearly two-hour drive delivers you to Évora, capital of the Alentejo region, and your base for the next two nights. Your boutique hotel was fashioned out of a palatial house located beside a 16th-century aqueduct within the city walls. Like the town itself, the hotel beautifully blends historical and contemporary styles.

After time to settle in and refresh, reunite with your fellow travelers and guides, and savor a memorable welcome dinner featuring locally sourced ingredients paired with a glass (or two!) of regional wine.

Included Meals: Breakfast, Dinner

Today’s walk in the Alentejo traverses typical Mediterranean landscapes dotted with cypress, pomegranate, fig, and ancient olive trees. You depart from the tiny, rural village of Outeiro and soon reach the first of many dolmens and menhirs scattered across the surrounding plains. The area boasts nearly 150 of these carved-rock monoliths and piled structures. Similar to those found in western Ireland, they date from the third and fourth millennia.

A sustained 30-minute climb along a cobbled path brings you to the picturesque hilltop village of Reguengos de Monsaraz, designated the European Wine Capital in 2015. (Your minibus and driver provide a lift up to the village for those who prefer to skip the climb.) From this vantage point you see a huge, modern dam and the Alqueva Lake on one side, and to the East, the Spanish border. Enjoy lunch at a restaurant of your choice, dining at one of the many restaurants with a scenic outdoor terrace, perhaps. Afterward, there is time to stroll this atmospheric village whose cobbled slate streets with whitewashed houses retain an authentic feel. Pop into artisan studios, and be sure to visit the castle, which now houses a bullring within its walls!

Upon your return to Évora, you embark on a walking tour of this fascinating town with your guides—exploring the city’s historic center, including the ancient Roman Temple of Diana (or Temple of Évora) and the Cathedral of Évora, a massive Gothic structure begun in the 12th century. You also visit the Igreja de São Francisco, which features Gothic and baroque architecture and the skeleton-adorned Chapel of Bones. Once an important city for trading and religious purposes, today, Évora is a vibrant university town. Continue exploring on your own or return to your hotel for a relaxing swim in the pool or treatment at the Spa Aqueduto. This evening, enjoy dinner at a restaurant of your choice. Recommendations are provided by your guides.

Included Meals: Breakfast

Bid farewell to Évora and travel south (two hours) to the Parque Natural do Costa Vicentina in the southwestern region of Baixo (lower) Alentejo. Soaring cliffs blanketed with pine trees skirted by pristine beaches make this one of Europe’s best-preserved coastlines. In this undisturbed corner of Portugal, a rich biodiversity has emerged. During the next few days as you walk the Rota Vicentina, or Fishermen’s Trail, you’ll discover a stunning variety of vegetation, more than 20 species of birds, and other coastal fauna. This historical long-distance path was used by fishermen and locals to get to the best fishing areas and most-secluded beaches.

You reach the town of Cavaleiro and enjoy a midday meal of petiscos (small plates) ranging from local cheese and ham to seafood and rice dishes. You depart on foot 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. Along this section of the Fishermen’s Trail, you’ll make your way from the Cabo Sardão lighthouse 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). 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 paths down to inviting beaches.

You arrive on foot at your hotel—a cattle-breeding working estate run by the same family since 1826. Set on a tranquil 900 acres within view of the Atlantic Ocean, its thoughtful design keeps you connected to the Alentejo’s rural beauty, with outdoor terraces and open spaces that afford breathtaking views. Enjoy a welcome drink as the sun sets the sky ablaze while it disappears behind the Atlantic. Then, make your way to your hotel’s cozy restaurant for a delicious dinner of fresh cod (prepared one of 365 ways!) served with local seasonal vegetables, and paired, of course, with one of the region’s fine wines.

Included Meals: Breakfast, Lunch, Dinner

After another hearty breakfast, drive 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, which 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 Algarve regions of Portugal.

Today’s walk is more undulating (and challenging!) as you ascend and descend to and from 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 you’ll even spot 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. You might see the hanging ropes the locals use 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 scenic footpaths to Praia da Amalia beach, which is difficult to access except by foot. This 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 through more magnificent vistas. Your walk concludes in Zambujeira do Mar. Take time to linger in a café or peruse the small shops, then return to your hotel where you refresh and relax before dinner at a favorite restaurant featuring bounty from the sea.

Included Meals: Breakfast, Lunch, Dinner

After breakfast, you travel north to the Setúbal Peninsula, stopping en route for another walk along the Fishermen’s Trail. Today, you’ll make your way from Cavaleiro to Praia do Almograve, along a dramatic route with contrasting sights—black rock outcrops and vast expanses of golden, shifting sands. As the trail nudges near the edge of the beach, you’ll pass by rock pools teeming with marine life. Further inland, you’ll find the landscape blanketed by “ice” plants with colorful flowers that shimmer in the sunlight as though encased in ice. Approaching the fishing harbor of Porto das Lapas das Pombas, local traditions come to life, as fishermen pull in the catch of the day in a picturesque setting.

Refuel over a lunch of local specialties in the village of Almograve before continuing (via a two-hour minibus drive) to your final destination—a historic pousada overlooking the hills of the Arrábida and the Atlantic. Settle in to your beautifully appointed room and relax on the terrace with an aperitif, or take a stroll around the expansive grounds.

Enjoy dinner on your own at the casual bar or in the elegant restaurant within the hotel, or step out to one of the casual dining options in town.

Included Meals: Breakfast, Lunch

Enjoy a leisurely breakfast, perhaps with a cup of café com leite, a Portuguese coffee-and-milk drink similar to a latte, in the former convent’s cloisters. Then, depart for this morning’s gorgeous walk along the Cabo Espichel, or Espichel Cape. Located on the southwestern tip of the Setúbal Peninsula, you’ll make your way through a primitive landscape of wind-blasted trees and towering cliffs with blue ocean waters glistening below. The peninsula boasts a series of spectacular hiking trails (your guide will choose the best route depending on the weather and trail conditions). Highlights along the way include the Cabo Espichel Lighthouse, the Chapel of Ermida da Memória, and two sets of dinosaur footprint fossils.

Lunch is at the restaurant of your choice in the picturesque fishing port of Sesimbra, nestled at the foothills of the Serra da Arrábida Natural Park. Your guides provide recommendations of where to try a meal of fried cuttlefish or another catch of the day. Then, return to your hotel with a stop en route in Azeitão for a wine tasting (and maybe a sample of the famous local cheese) and the opportunity to explore the town. Stop in at an artisan’s workshop for a closer look at the tile-making or other artisanal crafts and, perhaps, pick up a souvenir. Back at your accommodation, you’ll have time to relax in one of the hotel’s common spaces, a glass of the area’s famous muscatel in hand before gathering for a festive evening celebration to toast the week’s adventures.

Included Meals: Breakfast, Dinner

Adeus! Your Portugal walking tour concludes after an included breakfast and complimentary transportation to Lisbon (by 12:00 p.m.). Stay and continue exploring or depart for your onward travels.

Included Meals: Breakfast