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Alentejo’s charming villages, boundless landscapes, and sunny coastlines will leave you longing for more on this Self-Guided Walking tour in Portugal.

The crystal-clear notes of a Portuguese guitar ring through the candlelit club, and the singer strikes up a haunting fado melody. Portugal’s iconic music is all about longing, and that’s exactly what you’re feeling as you sip a glass of Alentejo red and reflect on your amazing adventure on this Self-Guided Walking tour in Portugal. You could have lingered forever strolling Marvão’s castle ramparts, or wandering medieval paths through São Mamede’s cork and chestnut forests. Then there was Évora, with its whitewashed Moorish alleys, Roman ruins, and Gothic treasures. Carefree days browsing for hand-embroidered Arraiolos rugs, walking Odeceixe’s bluffs and beaches, exploring Lisbon’s winding streets and tile-covered praças…. Honestly, if you could choose, you’d do it all over again! And as this music says so well, wistfulness is just another side of joy.


  • Walk the superb medieval pathways that have long linked the historic stone villages of Serra de São Mamede Natural Park.
  • Follow a local guide through the city of Évora, a magnificent time capsule of the medieval age and a UNESCO World Heritage site.
  • Trace the spectacular trails of the Rota Vicentina along high Atlantic cliffs, stopping to explore fishing villages and to soak your feet in refreshing waters.
  • Conclude your guided tour of Lisbon with a live performance of soulful “fado,” Portugal’s traditional music, during a special farewell dinner.
On all Self-Guided Adventures you can count on...
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A local representative available 24/7
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Detailed maps & route notes featuring turn-by-turn directions and places of interest
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Delicious meals—many are included
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Scheduled taxi transfers to bring you to and from each day’s walks (excluding self-drive adventures)
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Gracious accommodations that are a clean, comfortable home away from home
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Experts to handle all the details, including moving your luggage between hotels while you’re out exploring
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Access to a Self-Guided Flight Concierge—ask our knowledgeable team to find flights that sync with your planned trip


This tour can be requested starting any day of the week, except for Friday*, from March 1 through June 30 and September 15 through November 15, 2022 (*due to the closure of the Arraiolos Tapestry Interpretive Center on Mondays), subject to availability

Show Itinerary:

Arrive in Lisbon and, with a Country Walkers representative, make your way to Alto Alentejo. In this northern region of Portugal’s rustic Alentejo Province, cattle, sheep, and black pigs dot the farmlands. In just under three hours, you will arrive in one of the country’s most dramatic settings—the medieval, hilltop village of Marvão, one of Portugal’s most spectacular fortified villages. Located in the heart of the Serra de São Mamede Natural Park, Marvão drapes down a ridge of the park’s namesake mountain range and offers sweeping views of the Alentejan plains and the Spanish frontier, just 10 miles away. Perhaps you will spot the Bonelli’s eagle during your two-night stay; the presence of raptors has earned the town the nickname “The Eagle’s Nest.” You will feel the allure of this tranquil place, as you meander narrow lanes lined by pristine whitewashed houses adorned with Portugal’s traditional azulejo tiles.

For an invigorating warm-up walk, head to the town’s imposing, largely crusader-era castle, for breathtaking views, strolls along the ramparts, and a glimpse of its massive cistern where both rainwater and eerie echoes have collected for centuries. A lovely contemporary of the castle, the Igreja de Santa Maria (the village church), hosts a museum of artifacts that span the ages. This evening, find the ideal spot to view a spectacular sunset over the plains. Savor your first dinner at your pousada, perhaps sampling a carefully prepared codfish or pork served with migas, a savory bread crumb pudding made with garlic and olive oil. As you dine, you’ll take in magnificent views of the countryside below through your dining room’s floor-to-ceiling windows.

Included Meals: Dinner

7.6 miles, easy to moderate, 1,350-ft. cumulative elevation gain and 350-ft. cumulative elevation loss

Look forward to a hearty breakfast of hot and cold selections every day throughout your journey, including fruit, cold cuts, cheese, yogurt, and eggs. Following today’s morning meal, take a 15-minute taxi ride to the starting point of your walk, the tiny village of Galegos. This charming hamlet is in the heart of the Serra de São Mamede Natural Park, a preserved landscape of agriculture and forests dense with oak and chestnut trees. As you get underway, you ascend a pathway past stone walls and sheep grazing in fields until you reach the fascinating Spanish frontier town of La Fontañera. During the Spanish Civil War, smugglers used La Fontañera as a base to exchange one of the most valuable contrabands between Portugal and Spain—coffee. The bean had been banned by the dictatorial regime, and covert coffee smuggling operations grew into a big business between 1935 and 1960. You may take some time to explore the village’s charming main street, then continue along the smuggling path, romanticized by local lore, poets, and writers. Once you reach the Zona de Espera dos Contrabandistas, where smugglers clandestinely met in the dead of night, take in picturesque views of Marvão high on its hill. Follow the banks of the Sever River and you’re sure to find the ideal picnic spot for the packed lunch provided by your pousada. A gently rolling landscape leads out past enormous granite boulders, ancient stone walls, and beautiful montados, or cork oak woodlands. Alentejo is the kingdom of cork, home to the largest forests in the world—more than half of the world’s cork supply originates here. One tree produces an impressive 4,000 wine bottle corks. After your rest, follow a medieval cobbled path, ascending through the montados, to Marvão. Dinner tonight is on your own in town.

Included Meals: Breakfast, Lunch

6.4 miles, easy to moderate, 500-ft. cumulative elevation gain and 1,300-f.t cumulative elevation loss

Depart Marvão by foot this morning through one of its four village gates, the Porta de Ródão. Your downhill walk follows a well-preserved medieval cobbled path along Urra, the small hill connecting Marvão to the fortified town of Castelo de Vide, your destination. The chestnut groves you traverse are a treasured PDO (Protected Destination of Origin) for the beloved Marvão chestnuts they produce. The nut’s harvest, along with the season’s latest wine, is honored each November during the Marvão Chestnut Fair, a celebration of dancing, singing, and street performances. Listen for the gentle peal of sheep bells as you make your way along grassy dirt paths, stone walls, and cobbled and paved roadways leading past small farms of olive groves, into a stunning forest of Pyrenean oak. Throughout today’s walk, you may pause at various signposts to learn about the ancient foundations, traditional huts, and churches you’ll encounter along the way. Upon arrival at Castelo de Vide, enter through the main gate, the Arco de Santa Catarina, and stroll into the elegant main square, the Praça Dom Pedro V, watched over by 17th- and 18th-century Baroque buildings, churches, and the Town Hall.

The roots of Castelo de Vide stretch back to Roman times. In the Middle Ages, the Jewish population here flourished, establishing one of Europe’s most-thriving Jewish Quarters, the Judiaria. Time seems to have forgotten this historic district of cobbled streets and whitewashed houses with Gothic doorways. The oldest synagogue in Portugal is here, though all that remains of it is a small room. The town’s 14th-century castle houses its own medieval quarter, dripping with an ancient ambiance. Have lunch on your own, then take time to explore the Jewish Quarter and perhaps follow flower-lined lanes up to the castle. You will meet your driver this afternoon for a two-hour drive to Évora. Upon arrival, you’ll find a wide array of restaurants to choose from for dinner.

Included Meals: Breakfast

3 miles, easy

Medieval Évora, a UNESCO World Heritage site, is a virtual open-air museum, a stunning collection of buildings spanning every age. The Romans knew the city under the name Ebora Liberalitas Julia, bestowed upon it by Julio Cesar, and then the Moors called it home for the next 450 years. After the Moors were expelled, Portuguese kings transformed Évora into their center of learning and culture. The fruits of this most-prolific time still stand in the Old City—from the remarkably preserved 16th-century patrician houses to a splendid Gothic cathedral. An enormous ancient aqueduct slices through Évora, and far from an intrusion, it has been seamlessly and brilliantly incorporated into the city’s design.

After breakfast, explore this magnificent time capsule of a city. Meander through atmospheric Moorish alleyways lined with old patrician mansions and whitewashed houses with bright yellow trim. Your route leads you to the Roman baths beneath the current Town Hall and to the imposing Sé Cathedral, the country’s largest Gothic medieval cathedral. Next door, the Évora Museum in the former archbishop’s palace is a trove of ecclesiastical treasures, including period furnishings. The gallery of Flemish paintings features Life of the Virgin, a 13-panel masterwork dating to 1500. Stop by the São Francisco to view its Chapel of Bones, lined with the bones and skulls of nearly 5,000 souls. Throughout the morning, you will pause at each of these remarkable landmarks and hear about their rich history from your guide. Follow your discoveries with a wine tasting at a fine shop in the heart of Évora.

Continue to the charming town of Arraiolos, dominated by its impressive circular castle. Since the 16th century, exquisite wool tapestries have been hand-woven here to adorn the palaces and manor houses of Portuguese kings and counts. Pause for a lunch of petiscos, a tapas-like Portuguese style of dining with many small plates of food. Perhaps you’ll sample charcuterie, sheep’s cheese, minced chicken pie, or acorn-flour biscuits. Once your appetite is satisfied, take a stroll past pretty whitewashed houses with a blue trim meant to ward off the devil. In the main square, visit the Arraiolos Tapestry Interpretive Center, housed in a medieval-era hospital, where you can peruse an impressive collection of carpets and learn about the preservation of this traditional craft. Peer through the glass floors to see the dying pits once used to color the wool. You may have the chance to witness an artisan at work while you’re here. After a coffee break in a local café and time to select your own carpet, continue to the Almendres Cromlech. This incredible megalithic circle of 95 stones, set on a scenic hillside among olive and cork trees, dates from 5000-4000 BC and was likely central to the sacred rituals of an ancient civilization. Back in Évora, you have many restaurants to choose from for dinner on your own.

Included Meals: Breakfast, Lunch

5 miles, easy, no elevation gain or loss

Another full breakfast starts your day. Then a taxi takes you 2.5 hours to the southwestern region of Baixo Alentejo. 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 two 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 at the lighthouse at Cabo Sardão, perhaps enjoying your picnic lunch on its grounds before setting off.

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, Lunch, Dinner

4.2-mile, 6-mile, or 8.7-mile options, easy to moderate, 1,200-ft. cumulative elevation gain and 1,100-ft. cumulative elevation loss

Begin today 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 begins along a pathway 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, Lunch, Dinner

3–5 miles, easy

A taxi takes you to Lisbon this morning, about 2.5 hours away. After lunch on your own, meet your local guide for a private walking tour that focuses on Lisbon’s traditional azulejo tiles. Deeply embedded in Portugal’s history and culture, these beautiful glazed ceramic tiles are a dominant feature of Lisbon, and they decorate everything from church and monastery walls to palaces, ordinary homes, park benches, fountains, shops, and train stations. Your walk concludes with an informative visit to the internationally acclaimed Santa Rufina tile workshop near the Castelo São Jorge in the heart of the Old City.

This evening, participate in a cherished Portuguese tradition—a fado show with dinner. You will head to the Clube de Fado in the heart of Alfama to indulge in fine Portuguese cuisine amid the strains of a traditional 12-stringed guitar and the sultry voices of the city’s best fado singers, or fadistas. Fado conveys mourning and longing, or saudade. It can be described as a feeling of loss, often associated with the sea or the struggles of the poor, and its history can be traced to the 1820s, but its precise origin may stretch back centuries. During your meal, fado etiquette dictates that you refrain from eating and talking during a performance. Sipping your wine, naturally, is encouraged. At Clube de Fado, owned by renowned fado guitarist Mario Pacheco, each performance lasts about 15 minutes, followed by a 15-minute break, making for a perfectly paced experience. It’s the ideal way to bid farewell to Portugal!

Included Meals: Breakfast, Dinner

After breakfast, you may depart at your leisure. We recommend spending an additional day or two in this fascinating historical city.

Included Meals: Breakfast


What's Included

Tour Only
Boutique accommodations Check
15 meals: 7 breakfasts, 4 lunches, and 4 dinners Check
Detailed water- and tear-resistant Route Notes, maps, and use of a handheld GPS unit Check
Orientation meeting with a Country Walkers representative Check
Local representative available 24/7 Check
Scheduled taxi and luggage transportation (Please note: If unable to walk, it is possible to travel with your luggage from one accommodation to the next; there may be an additional charge.) Check
Entrance fees and special events as noted in the itinerary: One wine tasting; guided walking tour of Évora (including entrance to the Roman baths, Sé Cathedral, Church of St. Francis, and Chapel of Bones); guided visit of the Arraiolos Tapestry Interpretive Center and Almendres Cromlech; guided walking tour of Lisbon. Check
Travel assistance available 24/7 provided by Allianz Global Assistance Check
Access to Self-Guided Flight Concierge—Ask our knowledgeable team to find flights that sync perfectly with your planned trip. Check
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Having been on several Vermont Bike Tours in the past, we had high expectations for our first Country Walkers Tour. The planning and execution of this self-guided Portugal tour simply could not be improved on. Each hike - from mountains to seacoast - was beautiful, accurately described, and fully supported not only by maps and detailed directions, but also by a GPS satellite system that beeped if you ever went off trail! Accommodations were all 4-star, and the breakfasts and the included dinners were excellent. In short, this was a memorable week of travel that far exceeded even our high…

Drew, Santa Fe, NM

Portugal: Porto to Lisbon

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