Portugal: Sintra & Rota Vicentina

3.9 miles, easy to moderate, 850-ft. elevation gain and loss

After breakfast, set off on a rewarding, mostly shaded loop into the Sintra-Cascais Natural Park. Before you get underway, though, consider stopping to pick up ingredients for a picnic lunch that you can enjoy on the trail. Be sure to include a heavenly local treat: Sintra’s own travesseiros—a flaky, almond-filled, pillowy pastry from a local bakery. We recommend Sintra’s oldest and most popular padaria, Casa Piriquita, conveniently located along your route.

Your first destination is the Quinta da Regaleira. The eclectic Quinta was designed on a nearby mountainside, adorned with lush gardens, lakes, grottoes, and touches said to have been inspired by alchemy. The 14th-century palace is a beloved landmark for its varied architecture and the elegant, glazed tiles that grace its walls. (Entrance fee is at your own expense and may be booked at time of visit.)

From here, climb the hillside over dirt and cobbled pathways and stretches of roadway to Pena Palace, one of Portugal’s most beloved landmarks and the pinnacle of Portuguese royalty’s lavish lifestyle. You may want to tour the interior of this pink-and-yellow confection, left much as it was in 1910 when the Portuguese Republic was declared and the monarchy left. Its gardens are also a delight to stroll.  A final short ascent delivers you to the Castelo dos Mouros (Moorish castle) high on granite cliffs before you gently loop back down to your hotel. (Entrance fee to the castle is at your own expense and may be booked at time of visit.)

If time allows this afternoon, you may wish to add on a visit to Villa Sassetti, a pretty castle-like home built by a wealthy local in the 1890s and later purchased by the town of Sintra. Just a short climb from the hotel through lush gardens, this out-and-back walk is also a rewarding option if you arrive later in the day or if you prefer a less demanding start to your adventure.

Early evening, meet a Country Walkers representative for an hour-long orientation meeting, then stroll to dinner on your own. Perhaps try the region’s famed Mercês pork or a seafood dish prepared with the daily catch from the Atlantic.

Included Meals: Breakfast

4.7–10.7 miles, moderate, 300-ft. elevation gain and 1,800-ft. elevation loss

Enjoy a hearty Portuguese breakfast at your leisure this morning. Then a taxi takes you 30 minutes to the Sanctuary of Peninha, an historic and scenic highlight of Sintra-Cascais Natural Park. This seaside chapel, along with its adjacent palace, strikes a dramatic pose atop a 1,500-foot outcrop. Marvel at magnificent views of the Atlantic, the coastal city of Cascais (where you’ll stay tonight), Sintra, and Lisbon. The chapel’s origins lie in the 16th century, when a young shepherdess claimed to have seen an apparition of the Virgin Mary. But monks did not build the structure until well over 100 years later, completing it in 1711.

This heavenly perch along the Serra de Sintra mountains is the starting point of your walk. You meander downhill along a dirt road through Mediterranean brushland marked by colorful wild meadows and low bushes, then traverse a coastal forest nourished by frequent misty fogs that roll in from the ocean. Walk through the charming villages of Biscaia and Figueira do Guincho before you reach the coastline. A cliffside footpath leads you past the remote Praia da Grota and the Praia do Abano. At the latter, perhaps stop for refreshment at a beach bar.

Later, arrive at the spectacular Praia do Guincho. In the summer, northern winds lure kitesurfers and windsurfers, while wintertime easterly winds bring larger swells—and traditional surfers. Explore the ruins of the Fort of Guincho while here, and perhaps grab lunch at a beach bar or eatery in town or on the neighboring Praia da Cresmina or Praia da Arriba. Later, a flat paved path delivers you to the pretty fishing town of Cascais. You’ll find benches along the way to rest and gaze out to the ocean. At the outskirts of town, you pass the Farol da Guia lighthouse and the Boca do Inferno, scenic seaside cliffs with an open cave.

Cascais was put on the map as a haven for sea lovers in the 1870s, when King Luis I and the royal family claimed it as their September residence. Other Portuguese nobility followed, and a summer community blossomed. Royalty from other nations have tested the waters, too, including dukes and kings from England, Spain, and Italy. After settling into your oceanside hotel, you might walk the ten minutes into the town’s historic center, where you can find a tempting spot for dinner on your own.

Included Meals: Breakfast

5.7 miles, easy to moderate, 350-ft. elevation gain and 300-ft. elevation loss

Another full, locally sourced breakfast starts your day. Then you journey 2.5 hours south along the coast to the southwestern region of Alentejo and Vicentine Coast Natural Park. This is one of Europe’s best-preserved coastlines, draped in pristine beaches and soaring cliffs dotted with umbrella-like pine trees. You’ll witness a rich biodiversity and an authentic, welcoming culture in this exceptional corner of Portugal. For the next several days, you will walk the Rota Vicentina, a long-distance hiking path long used by fishermen and locals to access the best fishing spots and remote beaches.

Begin today’s breathtaking walk in small, whitewashed Cavaleiro. The village’s name is Portuguese for “knight,” but you’ll find it more charming than grand. Perhaps grab a bite to eat or fixings for a picnic at a local restaurant or café. Then head out of the village by foot, following a road that skirts wide farming fields and leads into coastal scrub. It’s just a mile before you reach the lighthouse at Cabo Sardão, the westernmost point of Alentejo. The landmark is rare because the light tower was built on the land side of the site, rather than on the sea side. But this detail surely won’t distract from the spectacular ocean and coastal views you’ll enjoy. It’s the ideal spot for a picnic lunch.

Commence your walk along the Fishermen’s Trail, traversing high dramatic cliffs amid red-hued earth and sandstone, keeping your eyes open for the more than 20 species of birds that nest here. Watch for jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon. Watch also for storks; this is the only place in the world where they nest on cliffs. This spectacular coastal trail reveals Portugal at its wildest, taking you along a passage over high ledges through salt-tinged brush with sweeping views of the Atlantic. Absorb the magnificent beauty at an easy pace before arriving at your next hotel, where dinner is served on site.

Included Meals: Breakfast, Dinner

4-mile, 6.7-mile, or 9.4-mile options, easy to moderate, 850-ft. cumulative elevation gain and 800-ft. cumulative elevation loss

If you wish, request a packed lunch from the hotel before setting out. Or plan to take a break for lunch at one of the beachside cafés you’ll encounter today.

Begin on the White Summit, or Ponta em Branco, named for the color of its sediment. Here, marvel at one of Alentejo’s most spectacular views—Odeceixe Beach, or Praia de Odeceixe, against the backdrop of Mount Fóia, part of the Serra de Monchique range. The scenic Seixe River marks the border between Alentejo and the Algarve. Continue walking the cliffside Fishermen’s Trail, gazing down at the pristine gold-sand beaches below, many of them accessible only via hanging ropes used by locals to gather shellfish. You’ll have a choice of three walks today, from longest to shortest, with each starting point marked below.

The longest option from Praia de Odeceixe leads you into the domain of the Egyptian mongoose, weasel, badger, and other nocturnal mammals. The schist and graywacke of the rocky cliffs were formed by sand, clay, and ash compressed at the bottom of an ancient ocean over millennia. Soon, you’ll arrive at Azenha do Mar (the starting point for today’s medium-length walk). This natural fishing harbor is an idyllic spot to pause for a cold drink at an outdoor restaurant. As you continue, you might spot an endemic rabbit species; all rabbits are said to have descended from this local type. As the preferred prey of carnivores, rabbits are crucial to the balance of nature along this coast.

From Praia da Amália (starting point for the day’s shortest route), make your way along many ascents and descents to beaches of unimaginable beauty. Packed-dirt trails lead through forests of pine, evergreen, oak, and eucalyptus. Follow deep-sand paths through heath landscapes that hug the shore. At Praia dos Machados, watch for stork nests along the cliffs, and at Praia do Carvalhal, you may catch a glimpse of surfers in the water. Finally, follow the signpost down a staircase to Praia dos Alteirinhos to lie in the sand and soothe your feet in cool, refreshing waters. End the day’s invigorating walk in the sleepy seaside village of Zambujeira do Mar, where small shops and cafés beckon. Linger here for a while before returning to your hotel for dinner.

Included Meals: Breakfast, Dinner

7.8 miles, easy to moderate, 750-ft. elevation gain and 550-ft. elevation loss or 5 miles, easy to moderate, 500-ft. elevation gain and 400-ft. elevation loss

Set off after breakfast this morning on a 45-minute taxi ride inland. You alight at the Barragem de Campilhas, a serene reservoir built in 1954 as part of an agricultural irrigation project.

From here, you embark on the Historical Way, one of two long-distance routes of the Rota Vincentina—twice certified one of the “Leading Quality Trails – Best of Europe” by the European Ramblers Association. Along this section of this celebrated route, you’ll touch local history and culture, as you pass through whitewashed villages and stands of forest separated by cow pastures. Ponds and streams, reed-ringed marshes, olive groves, orchards, gardens, and rocky outcrops also greet your gaze as you walk.

Around lunchtime, you arrive at Cercal do Alentejo, a cozy town named for its abundance of oak trees. Admire its 17th-century parish church and perhaps enjoy lunch at a local café or restaurant. If you prefer to skip the walk along the Historical Way, you can taxi here directly and take more time to explore its traditional village center.

From Cercal do Alentejo, pass through the outskirts of town and into a wonderland of vegetable gardens, orchards, and farms, where life passes to the rhythm of the seasons. Don’t miss the famous strawberry bush, remarkably tree-like in proportion.

Your final stop today is the Herdade da Matinha, a magical oasis dedicated to nature and the arts, and your home for the next two nights. An underlay of soothing classical music accompanies your delicious gourmet dinner, influenced by your hosts’ European, African, and Jewish family heritage.

Included Meals: Breakfast, Dinner

8.3 miles, easy to moderate, 250-ft. elevation gain and 750-ft. elevation loss

Enjoy locally baked bread, freshly squeezed juice from the estate’s own trees, homemade cakes, and more for breakfast this morning. If you wish, you may also request a picnic lunch to savor later, overlooking the sea.

Then, set out on foot, heading west through a countryside lush with eucalyptus and cork oak forests and farmlands, en route to the sea. Inhale the fragrance of lavender, thyme, calamints, rosemary, or other aromatic plants as you tread through this biodiversity hotspot. Many of the more than 150 species of plants that line your route are endemic to the Iberian Peninsula, and some only exist on Portugal’s southwest coast. Feel the presence of the sea in the air as you take in the blue horizon.

As you’ll see, wheat fields dominate the coastal plateau, where the larks, pipits, corn buntings, and warblers cheer the landscape. Kestrels, small birds of prey, fly over the wheat fields, but these birds have perfected the camouflage essential to escaping predators, especially the nesting females. The lark’s nest is a geometrically perfect cup, dug into the ground and lined with dried herbs and moss, and so mimetic that you might look directly at it and not even realize that it’s there.

When you reach the coast at Praia da Ilha do Passeguiro, turn north along the Fisherman’s Trail, a spectacular stretch of the Rota Vincentina. Steep cliffs give way to windswept sand dunes as you walk. Not far offshore, you’ll see Ilha do Pessegueiro (Peach Tree Island), thought to be named for the fish salting that used to occur here in Roman times. A 16th-century fortress looms over the beach and is popular with history buffs and amateur photographers, and traces of the ruins of Forte do Santo Alberto may still be seen.

Continuing north, pass Praia do Sissal, Praia da Engardaceira, and Praia da Baia de Porto Covo—an enticing trio of beaches—and enter Porto Covo, a sleepy fishing village that was once a Carthaginian trading post. Enjoy time at leisure to soak in its picturesque charm as you stroll cobbled streets past whitewashed buildings with red doors and blue trim, relax with a cup of coffee at colorful Marquês de Pombal Square, and perhaps indulge in a swim from a secluded beach. If you didn’t bring a picnic from the hotel, this is a good spot to enjoy lunch at a local bar or restaurant. A taxi returns you to your hotel in time for tonight’s sumptuous farewell dinner.

Alternatively, you might spend the day immersing yourself in the peace and tranquility of the Herdade da Matinha, with its focus on nature and sustainability. Sit back and enjoy the ambiance, indulge in a massage, or admire the dazzling gardens. Or take advantage of other nearby activities (at your own expense), such as biking, surfing, paddleboarding, horseback riding, or a ferry ride.

Included Meals: Breakfast, Dinner

Depart your hotel at 9:30 a.m. A 2.5-hour taxi ride takes you to Lisbon, where you may spend an additional day exploring Portugal’s historic capital.

Included Meals: Breakfast

3.9 miles, easy to moderate, 850-ft. elevation gain and loss

Make your own way to the Sintra Boutique Hotel in Sintra, situated in the Old Town. Lord Byron called this UNESCO World Heritage site “the most delightful village in Europe.” Plan to arrive early in the day, then set off on a rewarding, mostly shaded loop into the Sintra-Cascais Natural Park. Before you get underway though, consider stopping to pick up ingredients for a picnic lunch that you can enjoy on the trail. Be sure to include a heavenly local treat: Sintra’s own travesseiros—a flaky, almond-filled, pillowy pastry from a local bakery. We recommend Sintra’s oldest and most popular padaria, Casa Piriquita, conveniently located along your route.

Your first destination is the Quinta da Regaleira. The eclectic Quinta was designed on a nearby mountainside, adorned with lush gardens, lakes, grottoes, and touches said to have been inspired by alchemy. The 14th-century palace is a beloved landmark for its varied architecture and the elegant, glazed tiles that grace its walls. (Entrance fee is at your own expense and may be booked at time of visit.)

From here, climb the hillside over dirt and cobbled pathways and stretches of roadway to Pena Palace, one of Portugal’s most beloved landmarks and the pinnacle of Portuguese royalty’s lavish lifestyle. You may want to tour the interior of this pink and yellow confection, left much as it was in 1910 when the Portuguese Republic was declared and the monarchy left. Its gardens are also a delight to stroll. (Entrance to the palace is at your own expense and must be booked in advance at parquesdesintra.pt/en/parks-monuments/park-and-national-palace-of-pena.) A final short ascent delivers you to the Castelo dos Mouros (Moorish castle) high on granite cliffs before you gently loop back down to your hotel. (Entrance fee to the castle is at your own expense and may be booked at time of visit.)

If time allows this afternoon, you may wish to add on a visit to Villa Sassetti, a pretty castle-like home built by a wealthy local in the 1890s and later purchased by the town of Sintra. Just a short climb from the hotel through lush gardens, this out-and-back walk is also a rewarding option if you arrive later in the day or if you prefer a less demanding start to your adventure.

Early evening, meet a Country Walkers representative for an hour-long orientation meeting, then stroll to dinner on your own. Perhaps try the region’s famed Mercês pork or a seafood dish prepared with the daily catch from the Atlantic.

4.7–10.7 miles, moderate, 300-ft. elevation gain and 1,800-ft. elevation loss

Enjoy a hearty Portuguese breakfast at your leisure this morning. Then a taxi takes you 30 minutes to the Sanctuary of Peninha, an historic and scenic highlight of Sintra-Cascais Natural Park. This seaside chapel, along with its adjacent palace, strike a dramatic pose atop a 1,500-foot outcrop. Marvel at magnificent views of the Atlantic, the coastal city of Cascais (where you’ll stay tonight)—Sintra, and Lisbon. The chapel’s origins lie in the 16th century when a young shepherdess claimed to have seen an apparition of the Virgin Mary. But monks did not build the structure until 100 years later, completing it in 1711.

This heavenly perch along the Serra de Sintra mountains is the starting point of your walk. You meander downhill along a dirt road through Mediterranean brushland marked by colorful wild meadows and low bushes, then traverse a coastal forest nourished by frequent misty fogs that roll in from the ocean. Walk through the charming villages of Biscaia and Figueira do Guincho before you reach the coastline. A cliffside footpath lead you past the remote Praia da Grota and the Praia do Abano. At the latter, perhaps stop for a refreshment at a beach bar. Later, arrive at the spectacular Praia do Guincho. In the summer, northern winds lure kitesurfers and windsurfers while wintertime easterly winds bring larger swells—and traditional surfers. Explore the ruins of the Fort of Guincho while here, and perhaps grab lunch at a beach bar or eatery in town or on the neighboring Praia da Cresmina or Praia da Arriba. Later, a flat paved path delivers you to the pretty fishing town of Cascais. You’ll find benches along the way to rest and gaze out to the ocean. At the outskirts of town, you pass the Farol da Guia lighthouse and the Boca do Inferno, scenic seaside cliffs with an open cave.

Cascais was put on the map as a haven for sea lovers in the 1870s when King Luis I and the royal family claimed it as their September residence. Other Portuguese nobility followed and a summer community blossomed. Royalty from other nations have tested the waters, too, including dukes and kings from England, Spain, and Italy. After settling in to your oceanside hotel, you might walk the ten minutes into the town’s historic center, where you can find a tempting spot for dinner on your own.

Included Meals: Breakfast

5.7 miles, easy to moderate, 350-ft. elevation gain and 300-ft. elevation loss

Another full, locally sourced breakfast starts your day. Then you journey 2.5 hours south along the coast to the southwestern region of Alentejo and Vicentine Coast Natural Park. This is one of Europe’s best-preserved coastlines, draped in pristine beaches and soaring cliffs dotted with umbrella-like pine trees. You’ll witness a rich biodiversity and an authentic, welcoming culture in this exceptional corner of Portugal. For the next several days, you will walk the Rota Vicentina, a long-distance hiking path long used by fishermen and locals to access the best fishing spots and remote beaches.

Begin today’s breathtaking walk in the small, whitewashed Cavaleiro. The village’s name is Portuguese for “knight,” but you’ll find it more charming than grand. Perhaps grab a bite to eat or fixings for a picnic at a local restaurant or café. Then head out of the village by foot, following a road that skirts wide farming fields and leads into coastal scrub. It’s just a mile before you reach the lighthouse at Cabo Sardão, the westernmost point of Alentejo. The landmark is rare because the light tower was built on the land side of the site, rather than on the seaside. But this detail surely won’t distract from the spectacular ocean and coastal views you’ll enjoy. It’s the ideal spot for a picnic lunch.

Commence your walk along the Fishermen’s Trail, traversing high dramatic cliffs amid red-hued earth and sandstone, keeping your eyes open for the more than 20 species of birds that nest here. Watch for jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon. Watch also for storks; this is the only place in the world where they nest on cliffs. This spectacular coastal trail reveals Portugal at its wildest, taking you along a passage over high ledges through salt-tinged brush with sweeping views of the Atlantic. Absorb the magnificent beauty at an easy pace before arriving at your next hotel, where dinner is served on site.

Included Meals: Breakfast, Dinner

4-mile, 6.7-mile, or 9.4-mile options, easy to moderate, 850-ft. cumulative elevation gain and 800-ft. cumulative elevation loss

If you wish, request a packed lunch from the hotel before setting out. Or, plan to take a break for lunch at one of the beachside cafés you’ll encounter today.

Begin on the White Summit, or Ponta em Branco, named for the color of its sediment. Here, marvel at one of Alentejo’s most spectacular views—Odeceixe Beach, or Praia de Odeceixe, against the backdrop of Mount Fóia, part of the Serra de Monchique range. The scenic Seixe River marks the border between Alentejo and the Algarve. Continue walking the cliffside Fishermen’s Trail, gazing down at the pristine gold-sand beaches below, many of them only accessible via hanging ropes used by locals to gather shellfish. You’ll have a choice of three walks today, from longest to shortest, with each starting point marked below.

The longest option from Praia de Odeceixe leads you into the domain of the Egyptian mongoose, weasel, badger, and other nocturnal mammals. The schist and graywacke of the rocky cliffs were formed by sand, clay, and ash compressed at the bottom of an ancient ocean over millennia. Soon, you’ll arrive at Azenha do Mar (the starting point for today’s medium-length walk). This natural fishing harbor is an idyllic spot to pause for a cold drink at an outdoor restaurant. As you continue, you might spot an endemic rabbit species; all rabbits are said to have descended from this local type. As the preferred prey of carnivores, rabbits are crucial to the balance of nature along this coast.

From Praia da Amália (starting point for the day’s shortest route), make your way along many ascents and descents to beaches of unimaginable beauty. Packed-dirt trails lead through forests of pine, evergreen, oak, and eucalyptus. Follow deep-sand paths through heath landscapes that hug the shore. At Praia dos Machados, watch for stork nests along the cliffs, and at Praia do Carvalhal, you may catch a glimpse of surfers in the water. Finally, follow the signpost down a staircase to Praia dos Alteirinhos to lie in the sand and soothe your feet in cool, refreshing waters. End the day’s invigorating walk in the sleepy seaside village of Zambujeira do Mar, where small shops and cafés beckon. Linger here for a while before returning to your hotel for dinner.

Included Meals: Breakfast, Dinner

5.1 miles, easy to moderate, 500-ft. elevation gain and 450-ft. elevation loss

After breakfast, a taxi takes you 40 minutes further south into the stunning Algarve region, still within Southwest Alentejo and Vicentine Coast Natural Park. Today’s walk begins in Monte Clérigo, a charming fishing village of pink and white cottages and a beautiful golden beach backed by cliffs and dunes.

You’ll want to linger here for a while, grabbing coffee, pastries, and perhaps trail snacks in the village, before returning to the stunning Fisherman’s Trail. Numerous beaches stretch out below you as you trace the cliffside—Praia da Fateixa, Praia do Coelha, and Praia do Medo da Fonte Santa. Later, you reach the breathtaking promontory of Ponta da Atalaia and its adjacent Ribat da Arrifana. Founded by Ibn Qasî, a spiritual guide of Islam’s mystical practice of Sufism, it was home to warrior monks who once prayed over the waters here. Marvel at its cliffside setting before continuing to the top of the cliffs, home to a Mediterranean bushland ecosystem filled with aromatic plants that grow on the coastal dunes, including thyme, rosemary, myrtle, and lavender.

Your footpath leads you next to the ruins of the Fortaleza da Arrifana, overlooking the spectacular Praia da Arrifana, hugged by towering cliffs on either side. The fortress of Arrifana was built in 1635 during the reign of Filipe II to defend the coastline and local fishermen from attacks by sea. Though it has been destroyed twice, the nearby town of Aljezur rebuilt its entry so beachgoers can remember the region’s rich past. You’ll find several beach cafés and restaurants here for lunch. If you wish, take a dip in the refreshing waters before an afternoon taxi delivers you to your hotel for the next two nights. You can choose from its two restaurants for dinner on your own.

Included Meals: Breakfast

4.6 miles (return), easy to moderate, 500-ft. elevation gain and loss

After a delicious à la carte breakfast, choose from a range of things to do today in and around your resort. An optional walk leads directly from your hotel to nearby Canal beach, another beautiful spot popular with surfers. The descent down to the beach—and your uphill return back to the hotel—is along a quiet country road that is part of the Historical Way, the second of the two long-distance routes of the Rota Vicentina. While the walk to and from the beach is steep, the sweeping expanse of these sands is worth the effort, as is the little-known gem that rises from the water 1,000 feet offshore: the Pedra da Agulha, an astonishing rock formation whose name appropriately means “needle rock.”

A second option is to taxi 20 minutes (at your expense) to explore the lovely town of Aljezur. Though this region has been inhabited for millennia, it was formally founded by Moors in the 10th century. Christians moved in during the Reconquest, but the Moorish Aljezur Castle remains and is even one of the seven castles on the Portuguese flag. After visiting the castle and perhaps a museum or two, enjoy a leisurely lunch of fresh seafood and authentic regional dishes at one of the many nearby cafés or restaurants. Don’t leave town without popping into the Mercado Municipal—this small covered market offering fresh produce, meats, seafood, and other local products is a feast for the senses.

The Praia do Canal Nature Resort is a haven of tranquility and you may wish to spend the entire day simply relaxing here. The onsite spa and health club features a heated indoor swimming pool, an outdoor infinity pool with panoramic valley views and poolside dining, two massage rooms, a hammam, two saunas (one bio), indoor and outdoor relaxation zones, as well as a cold plunge tank for the most intrepid souls. Complementary yoga classes are often on offer and a wide range of treatments are available (at your own expense).

Enjoy your final dinner on your own this evening.

Included Meals: Breakfast

Depart your hotel at 9:30 a.m. A three-hour taxi ride takes you to Lisbon, where you can make your connections home or onward. Or spend an additional day in Lisbon exploring Portugal’s historic capital.

Included Meals: Breakfast

3.9 miles, easy to moderate, 850-ft. elevation gain and loss

Make your own way to the Sintra Boutique Hotel in Sintra, situated in the Old Town. Lord Byron called this UNESCO World Heritage site “the most delightful village in Europe.” Plan to arrive early in the day, then set off on a rewarding, mostly shaded loop into the Sintra-Cascais Natural Park. Before you get underway, though, consider stopping to pick up ingredients for a picnic lunch that you can enjoy on the trail. Be sure to include a heavenly local treat: Sintra’s own travesseiros—a flaky, almond-filled, pillowy pastry from a local bakery.

Your first destination is the Quinta da Regaleira. The eclectic Quinta was designed on a nearby mountainside, adorned with lush gardens, lakes, grottoes, and touches said to have been inspired by alchemy. The 14th-century palace is a beloved landmark for its varied architecture and the elegant, glazed tiles that grace its walls.

From here, climb the hillside over dirt and cobbled pathways and stretches of roadway to Pena Palace, one of Portugal’s most beloved landmarks and the pinnacle of Portuguese royalty’s lavish lifestyle. You may want to tour the interior of this pink-and-yellow confection, left much as it was in 1910 when the Portuguese Republic was declared and the monarchy left. Its gardens are also a delight to stroll.  A final short ascent delivers you to the Castelo dos Mouros (Moorish castle) high on granite cliffs before you gently loop back down to your hotel.

If time allows this afternoon, you may wish to add on a visit to Villa Sassetti, a pretty castle-like home built by a wealthy local in the 1890s and later purchased by the town of Sintra. Just a short climb from the hotel through lush gardens, this out-and-back walk is also a rewarding option if you arrive later in the day or if you prefer a less demanding start to your adventure.

Early evening, meet a Country Walkers representative for an hour-long orientation meeting, then stroll to dinner on your own. Perhaps try the region’s famed Mercês pork or a seafood dish prepared with the daily catch from the Atlantic.

4.7–10.7 miles, moderate, 300-ft. elevation gain and 1,800-ft. elevation loss

Enjoy a hearty Portuguese breakfast at your leisure this morning. Then a taxi takes you 30 minutes to the Sanctuary of Peninha, an historic and scenic highlight of Sintra-Cascais Natural Park. This seaside chapel, along with its adjacent palace, strikes a dramatic pose atop a 1,500-foot outcrop. Marvel at magnificent views of the Atlantic, the coastal city of Cascais (where you’ll stay tonight), Sintra, and Lisbon. The chapel’s origins lie in the 16th century, when a young shepherdess claimed to have seen an apparition of the Virgin Mary. But monks did not build the structure until well over 100 years later, completing it in 1711.

This heavenly perch along the Serra de Sintra mountains is the starting point of your walk. You meander downhill along a dirt road through Mediterranean brushland marked by colorful wild meadows and low bushes, then traverse a coastal forest nourished by frequent misty fogs that roll in from the ocean. Walk through the charming villages of Biscaia and Figueira do Guincho before you reach the coastline. A cliffside footpath leads you past the remote Praia da Grota and the Praia do Abano. At the latter, perhaps stop for refreshment at a beach bar.

Later, arrive at the spectacular Praia do Guincho. In the summer, northern winds lure kitesurfers and windsurfers, while wintertime easterly winds bring larger swells—and traditional surfers. Explore the ruins of the Fort of Guincho while here, and perhaps grab lunch at a beach bar or eatery in town or on the neighboring Praia da Cresmina or Praia da Arriba. Later, a flat paved path delivers you to the pretty fishing town of Cascais. You’ll find benches along the way to rest and gaze out to the ocean. At the outskirts of town, you pass the Farol da Guia lighthouse and the Boca do Inferno, scenic seaside cliffs with an open cave.

Cascais was put on the map as a haven for sea lovers in the 1870s, when King Luis I and the royal family claimed it as their September residence. Other Portuguese nobility followed, and a summer community blossomed. Royalty from other nations have tested the waters, too, including dukes and kings from England, Spain, and Italy. After settling into your oceanside hotel, you might walk the ten minutes into the town’s historic center, where you can find a tempting spot for dinner on your own.

Included Meals: Breakfast

5.7 miles, easy to moderate, 350-ft. elevation gain and 300-ft. elevation loss

Another full, locally sourced breakfast starts your day. Then you journey 2.5 hours south along the coast to the southwestern region of Alentejo and Vicentine Coast Natural Park. This is one of Europe’s best-preserved coastlines, draped in pristine beaches and soaring cliffs dotted with umbrella-like pine trees. You’ll witness a rich biodiversity and an authentic, welcoming culture in this exceptional corner of Portugal. For the next several days, you will walk the Rota Vicentina, a long-distance hiking path long used by fishermen and locals to access the best fishing spots and remote beaches.

Begin today’s breathtaking walk in small, whitewashed Cavaleiro. The village’s name is Portuguese for “knight,” but you’ll find it more charming than grand. Perhaps grab a bite to eat or fixings for a picnic at a local restaurant or café. Then head out of the village by foot, following a road that skirts wide farming fields and leads into coastal scrub. It’s just a mile before you reach the lighthouse at Cabo Sardão, the westernmost point of Alentejo. The landmark is rare because the light tower was built on the land side of the site, rather than on the sea side. But this detail surely won’t distract from the spectacular ocean and coastal views you’ll enjoy. It’s the ideal spot for a picnic lunch.

Commence your walk along the Fishermen’s Trail, traversing high dramatic cliffs amid red-hued earth and sandstone, keeping your eyes open for the more than 20 species of birds that nest here. Watch for jackdaw, shag, common kestrel, peregrine falcon, and the pure rock dove, the original species of pigeon. Watch also for storks; this is the only place in the world where they nest on cliffs. This spectacular coastal trail reveals Portugal at its wildest, taking you along a passage over high ledges through salt-tinged brush with sweeping views of the Atlantic. Absorb the magnificent beauty at an easy pace before arriving at your next hotel, where dinner is served on site.

Included Meals: Breakfast, Dinner

4-mile, 6.7-mile, or 9.4-mile options, easy to moderate, 850-ft. cumulative elevation gain and 800-ft. cumulative elevation loss

If you wish, request a packed lunch from the hotel before setting out. Or plan to take a break for lunch at one of the beachside cafés you’ll encounter today.

Begin on the White Summit, or Ponta em Branco, named for the color of its sediment. Here, marvel at one of Alentejo’s most spectacular views—Odeceixe Beach, or Praia de Odeceixe, against the backdrop of Mount Fóia, part of the Serra de Monchique range. The scenic Seixe River marks the border between Alentejo and the Algarve. Continue walking the cliffside Fishermen’s Trail, gazing down at the pristine gold-sand beaches below, many of them accessible only via hanging ropes used by locals to gather shellfish. You’ll have a choice of three walks today, from longest to shortest, with each starting point marked below.

The longest option from Praia de Odeceixe leads you into the domain of the Egyptian mongoose, weasel, badger, and other nocturnal mammals. The schist and graywacke of the rocky cliffs were formed by sand, clay, and ash compressed at the bottom of an ancient ocean over millennia. Soon, you’ll arrive at Azenha do Mar (the starting point for today’s medium-length walk). This natural fishing harbor is an idyllic spot to pause for a cold drink at an outdoor restaurant. As you continue, you might spot an endemic rabbit species; all rabbits are said to have descended from this local type. As the preferred prey of carnivores, rabbits are crucial to the balance of nature along this coast.

From Praia da Amália (starting point for the day’s shortest route), make your way along many ascents and descents to beaches of unimaginable beauty. Packed-dirt trails lead through forests of pine, evergreen, oak, and eucalyptus. Follow deep-sand paths through heath landscapes that hug the shore. At Praia dos Machados, watch for stork nests along the cliffs, and at Praia do Carvalhal, you may catch a glimpse of surfers in the water. Finally, follow the signpost down a staircase to Praia dos Alteirinhos to lie in the sand and soothe your feet in cool, refreshing waters. End the day’s invigorating walk in the sleepy seaside village of Zambujeira do Mar, where small shops and cafés beckon. Linger here for a while before returning to your hotel for dinner.

Included Meals: Breakfast, Dinner

7.8 miles, easy to moderate, 750-ft. elevation gain and 550-ft. elevation loss or 5 miles, easy to moderate, 500-ft. elevation gain and 400-ft. elevation loss

Set off after breakfast this morning on a 45-minute taxi ride inland. You alight at the Barragem de Campilhas, a serene reservoir built in 1954 as part of an agricultural irrigation project.

From here, you embark on the Historical Way, one of two long-distance routes of the Rota Vincentina—twice certified one of the “Leading Quality Trails – Best of Europe” by the European Ramblers Association. Along this section of this celebrated route, you’ll touch local history and culture, as you pass through whitewashed villages and stands of forest separated by cow pastures. Ponds and streams, reed-ringed marshes, olive groves, orchards, gardens, and rocky outcrops also greet your gaze as you walk.

Around lunchtime, you arrive at Cercal do Alentejo, a cozy town named for its abundance of oak trees. Admire its 17th-century parish church and perhaps enjoy lunch at a local café or restaurant. If you prefer to skip the walk along the Historical Way, you can taxi here directly and take more time to explore its traditional village center.

From Cercal do Alentejo, pass through the outskirts of town and into a wonderland of vegetable gardens, orchards, and farms, where life passes to the rhythm of the seasons. Don’t miss the famous strawberry bush, remarkably tree-like in proportion.

Your final stop today is the Herdade da Matinha, a magical oasis dedicated to nature and the arts, and your home for the next two nights. An underlay of soothing classical music accompanies your delicious gourmet dinner, influenced by your hosts’ European, African, and Jewish family heritage.

Included Meals: Breakfast, Dinner

8.3 miles, easy to moderate, 250-ft. elevation gain and 750-ft. elevation loss

Enjoy locally baked bread, freshly squeezed juice from the estate’s own trees, homemade cakes, and more for breakfast this morning. If you wish, you may also request a picnic lunch to savor later, overlooking the sea.

Then, set out on foot, heading west through a countryside lush with eucalyptus and cork oak forests and farmlands, en route to the sea. Inhale the fragrance of lavender, thyme, calamints, rosemary, or other aromatic plants as you tread through this biodiversity hotspot. Many of the more than 150 species of plants that line your route are endemic to the Iberian Peninsula, and some only exist on Portugal’s southwest coast. Feel the presence of the sea in the air as you take in the blue horizon.

As you’ll see, wheat fields dominate the coastal plateau, where the larks, pipits, corn buntings, and warblers cheer the landscape. Kestrels, small birds of prey, fly over the wheat fields, but these birds have perfected the camouflage essential to escaping predators, especially the nesting females. The lark’s nest is a geometrically perfect cup, dug into the ground and lined with dried herbs and moss, and so mimetic that you might look directly at it and not even realize that it’s there.

When you reach the coast at Praia da Ilha do Passeguiro, turn north along the Fisherman’s Trail, a spectacular stretch of the Rota Vincentina. Steep cliffs give way to windswept sand dunes as you walk. Not far offshore, you’ll see Ilha do Pessegueiro (Peach Tree Island), thought to be named for the fish salting that used to occur here in Roman times. A 16th-century fortress looms over the beach and is popular with history buffs and amateur photographers, and traces of the ruins of Forte do Santo Alberto may still be seen.

Continuing north, pass Praia do Sissal, Praia da Engardaceira, and Praia da Baia de Porto Covo—an enticing trio of beaches—and enter Porto Covo, a sleepy fishing village that was once a Carthaginian trading post. Enjoy time at leisure to soak in its picturesque charm as you stroll cobbled streets past whitewashed buildings with red doors and blue trim, relax with a cup of coffee at colorful Marquês de Pombal Square, and perhaps indulge in a swim from a secluded beach. If you didn’t bring a picnic from the hotel, this is a good spot to enjoy lunch at a local bar or restaurant. A taxi returns you to your hotel in time for tonight’s sumptuous farewell dinner.

Alternatively, you might spend the day immersing yourself in the peace and tranquility of the Herdade da Matinha, with its focus on nature and sustainability. Sit back and enjoy the ambiance, indulge in a massage, or admire the dazzling gardens. Or take advantage of other nearby activities (at your own expense), such as biking, surfing, paddleboarding, horseback riding, or a ferry ride.

Included Meals: Breakfast, Dinner

Depart your hotel at 9:30 a.m. A 2.5-hour taxi ride takes you to Lisbon, where you can make your connections home or onward. Or spend an additional day in Lisbon exploring Portugal’s historic capital.

Included Meals: Breakfast