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On this Portugal self-guided tour, you’re in good company. Fishermen, farmers, and royalty have all walked these trails before you.
This tour can be requested starting on any of the dates listed above (Sunday start only), subject to availability
3.8 miles, easy to moderate, 900-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 your arrival so you can meet late this morning with a Country Walkers representative for an orientation meeting. Then set off on a rewarding, mostly shaded loop into the Sintra-Cascais Natural Park; your destination is Pena Palace, one of Portugal’s most beloved landmarks. (Entrance to the palace is at your own expense; we recommend you book in advance to avoid long lines.) Before you get underway, consider stopping to pick up ingredients for a picnic lunch that you can enjoy on the trail.
Leave your hotel directly and walk to the Estrada de Pena, where you begin a short climb over cobblestones to Villa Sassetti, a pretty castle-like home built by a wealthy local in the 1890s and later purchased by the town of Sintra. Spend a little time exploring the grounds and lush gardens, then continue through the adjacent stone arch. The dirt trail passes Penedo da Amizade cliffs, a haven for rock climbers, in the Loureiros Forest. Soon, you pass the Castelo dos Mouros (Moorish castle) high on granite cliffs. (You can skip the edifice for now and visit it on your way back down to Sintra.) Climb the hillside up to Pena Palace, a pink and yellow confection and the pinnacle of Portuguese royalty’s lavish lifestyle. You may want to tour the interior, 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.
If you arrive early enough, or if you prefer a less demanding start to your adventure, stroll to the Quinta da Regaleira and Sintra National Palace for a visit. 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.)
Dinner tonight is on your own. Perhaps try the region’s famed Mercês pork or a seafood dish prepared with the daily catch from the Atlantic. Beforehand, though, reward yourself with 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.
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
6.5 miles, easy to moderate, 550-ft. elevation gain and 500-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
4.5-mile, 6.25-mile, or 8.9-mile options, easy to moderate, 950-ft. cumulative elevation gain and 850-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. When you arrive at Praia da Amália (starting point for the day’s shortest route), you may stop to swim. This beautiful beach is named for the house perched above that was built by a beloved fado singer, Amália Rodrigues.
From Praia da Amália, 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 as long as you’d like before returning to your hotel for dinner.
Included Meals: Breakfast, Dinner
6.8 miles, easy to moderate, 850-ft. elevation gain and 400-ft. elevation loss
After breakfast, a taxi takes you 40 minutes further south into the stunning Algarve region. Your starting point is in the lovely town of Aljezur, still within Southwest Alentejo and Vicentine Coast Natural Park. 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. In the main square, take time to admire the 18th-century Igreja de Nossa Senhora da Alva, built on the order of the local bishop after the devastating 1755 earthquake as a focal point for a new community. You can have lunch at one of the nearby cafés, or grab a picnic for the trail.
Your walk today along the Historical Way, the second of the two long-distance routes of the Rota Vicentina. You follow rural inland routes through stands of cork trees and among mountain ranges, valleys, rivers, and creeks.
Walk west out of town on paved surface into the valley of the Ribeira Aljezur. This river was once active with ships from Lisbon, Flanders, and Castile plying its waters to and from the Atlantic. Today, it’s a marshy expanse thick with reeds and yellow flag flowers. As you continue uphill through shrubs and tree heather, take in sweeping views of sand dunes and the beach at Amoreira.
Streams meander through these fields and floodplains, nourishing magnificent patches of cottonwood, alder, ash, tamarisk, and willows. A diverse array of plants, insects, birds, amphibians, and mammals thrives here and, in the spring, butterflies rival wildflowers in their profusion of color. Agriculture, too, is rich in diversity, but the sweet potato of Aljezur takes center stage. Continue through a mountainous region where the eucalyptus tree dominates.
After your remarkably scenic day, arrive at your hotel. You can choose from its two restaurants for dinner on your own.
Included Meals: Breakfast
9.5 miles, moderate, 1,200-ft. elevation gain and 700-ft. elevation loss or 5.3 miles, easy to moderate, 750-ft. elevation gain and 400-ft. elevation loss
After a hearty breakfast, a 20-minute taxi ride delivers you to the start of your final day’s walk through a mix of coastal cliffs, Atlantic coastline, peaceful forests of cork and Portuguese oak, and gentle hills and valleys. But you might want to linger awhile before getting started: Monte Clérigo is a charming fishing village of pink and white cottages and a beautiful golden beach backed by cliffs and dunes.
After grabbing coffee, pastries, and perhaps trail snacks in the village, you return 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. (This is the drop-off point for the shorter walk today). 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 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 continuing.
Next, you join the Historical Way once again, heading inland across a sandy heath before descending to the Canal beach and another beautiful spot popular with surfers. The descent down to the beach—and your uphill return back to the trail—is the steepest stretch of the whole route. But 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.” After time here, return to the walking trail to follow a scenic ridge back to the hotel.
Enjoy your final dinner on your own this evening.
Included Meals: Breakfast
Depart your hotel at 10:00 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
Dates & Prices
|2023 Dates||Number of Travelers||Pre Hotel Night - Sintra||Post Hotel Night - Lisbon|
|2+||Single Supplement||Solo Surcharge||2+||Single Supplement||2+||Single Supplement|
|Feb 19 - Feb 19||$3,445||$1,045||$1,145||$145||$145||$145||$145|
|Feb 26 - Feb 26||$3,445||$1,045||$1,145||—||—||—||—|
|Mar 12 - Mar 12||$3,445||$1,045||$1,145||—||—||—||—|
|Mar 26 - Mar 26||$3,445||$1,045||$1,145||—||—||—||—|
|Apr 16 - Apr 16||$3,445||$1,195||$1,145||$145||$145||$145||$145|
|Apr 23 - Apr 23||$3,445||$1,195||$1,145||—||—||—||—|
|Apr 30 - Apr 30||$3,445||$1,195||$1,145||—||—||—||—|
|May 7 - May 7||$3,445||$1,195||$1,145||—||—||—||—|
|May 14 - May 14||$3,445||$1,195||$1,145||—||—||—||—|
|May 21 - May 21||$3,445||$1,195||$1,145||—||—||—||—|
|Sep 3 - Sep 3||$3,945||$1,395||$1,145||$145||$145||$145||$145|
|Sep 10 - Sep 10||$3,945||$1,395||$1,145||—||—||—||—|
|Sep 17 - Sep 17||$3,945||$1,395||$1,145||—||—||—||—|
|Sep 24 - Sep 24||$3,945||$1,395||$1,145||—||—||—||—|
|Oct 1 - Oct 1||$3,845||$1,345||$1,145||$145||$145||$145||$145|
|Oct 8 - Oct 8||$3,845||$1,345||$1,145||—||—||—||—|
|Oct 15 - Oct 15||$3,845||$1,345||$1,145||—||—||—||—|
|Oct 22 - Oct 22||$3,845||$1,345||$1,145||—||—||—||—|
|Oct 29 - Oct 29||$3,845||$1,345||$1,145||—||—||—||—|
|Nov 5 - Nov 5||$3,445||$1,195||$1,145||$145||$145||$145||$145|
|Nov 12 - Nov 12||$3,445||$1,195||$1,145||—||—||—||—|
|Nov 19 - Nov 19||$3,445||$1,195||$1,145||—||—||—||—|