Enjoy a range of Portuguese landscapes—from coastal villages to cork-oak forests—on a leisurely seaside adventure.

In northern Alto Alentejo, trace the old smugglers’ roads of Serra de São Mamede Natural Park through cork-oak woodlands, exploring tiny hamlets and imposing castles. The Rota Vicentina hugs red sandstone seacliffs where storks nest, passing pristine beaches. Gently rolling hills slope to fertile farms dotted with cork trees, olive trees, and green vineyards. Pause in tiny fishing villages and soak your feet in the waters of the Atlantic. Break up your walks with full-day explorations of medieval Évora and magnificent Lisbon, a local guide leading you past remarkably preserved architecture that whispers of a rich history. Cap off your adventure with a live performance of fado, Portugal’s soulful cultural treasure.


  • 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 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.
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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.


Thu, Apr 30 to Tue, Jun 30 - 2020

Show Itinerary:

Arrive in Lisbon and make your way with a Country Walkers representative to Alto Alentejo, the northern region of Portugal’s rustic Alentejo Province of farmlands dotted with cattle, sheep, and black pigs. In just under three hours, you will arrive in one of the country’s most dramatic settings—the stunning 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 eagle during your two-night stay; the presence of raptors has earned the town the nickname “The Eagle’s Nest.” You, too, will have the afternoon to “nest” in this tranquil place, meandering along 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 pinnacle, its 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 been 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 from which 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.

Accommodation: Pousada de Marvão, Marvão
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 located 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, ascend a pathway uphill 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 the covert operation 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 peaceful picnic spot for your packed lunch, provided by your pousada. A gently rolling landscape points the way 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, impressive when you consider that one tree produces 4,000 wine bottle corks. A medieval cobbled path ascends through the montados, delivering you to Marvão. Dinner tonight is on your own in town.

Accommodation: Pousada de Marvão, Marvão
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 will 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 celebrated each November during the Marvão Chestnut Fair, a celebration of dancing, singing, and street performances. Listen for the gentle peal of sheeps’ 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. 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 grew here and established 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 was built 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 here, 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 transfer to Évora. Upon arrival, you’ll find a wide array of restaurants to choose from for dinner.

Accommodation: Albergaria do Calvário (also known as ADC Hotel), Évora
Included Meals: Breakfast

3 miles, easy

Medieval Évora, a UNESCO World Heritage site, is a virtual open-air museum, a stunning collection of buildings that span every age. The Romans knew the city under the name Ebora Liberalitas Julia, given by Julio Cesar, before the Moors called it home for 450 years. After the Moors were expelled, Portuguese kings transformed it into a center of learning and culture. The fruits of this most prolific time period still stand in the Old City, from the remarkably preserved 16th-century patrician houses to a splendid Gothic cathedral. Most impressively, an enormous ancient aqueduct slices through the city. 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 today’s 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 painting 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 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. Toast your discoveries with a wine tasting at a fine shop in the heart of the city.

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. Perhaps you’ll sample charcuterie, sheep’s cheese, minced chicken pie, or acorn flour biscuits. Satiated, you will 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.

Accommodation: Albergaria do Calvário (also known as ADC Hotel), Évora
Included Meals: Breakfast, Lunch (and Wine Tasting)

5 miles, easy, no elevation gain or loss

Another full breakfast starts your day. Then take a private two-and-a-half-hour transfer 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 very special 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, a passage over high ledges through salt-tinged brush with sweeping views of the Atlantic. Take your time and absorb the magnificent beauty at an easy pace before arriving at your next hotel where dinner is served on site.

Accommodation: Herdade do Touril, Zambujeira do Mar
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. Then continue walking the cliffside Fishermen’s Trail, passing 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.

Begin the longest option from Praia de Odeceixe, following the pathway into the domain of the Egyptian mongoose, weasel, badger, and other nocturnal mammals. The schist and greywacke of the cliffs was formed by sand, clay, and ash compressed at the bottom of an ancient ocean over millennia. Stop 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, they are crucial to the balance of nature along the coast. You may stop to swim at Praia da Amália (starting point for the day’s shortest route). This beautiful beach was named for the house perched above that was built by a beloved fado singer, Amália Rodrigues.

Today’s walk is more undulating, with many ascents and descents from and to beaches of unimaginable beauty. Follow packed-dirt trails through pine, evergreen, oak, and eucalyptus forest and deep-sand paths through heath landscapes that hug the shore. Watch for stork nests along the cliffs of Praia dos Machados and surfers at Praia do Carvalhal. 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.

Accommodation: Herdade do Touril, Zambujeira do Mar
Included Meals: Breakfast, Lunch, Dinner

3–5 miles, easy

A taxi takes you to Lisbon this morning, about two-and-a-half hours away. After lunch on your own, meet your local guide for a private walking tour focusing on Lisbon’s traditional azulejo tiles. Deeply embedded in Portugal’s history and culture, these beautiful glazed ceramic tiles are a dominant feature of the city, decorating everything from walls of churches and monasteries, 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 Sao 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 traditional cuisine, the strains of a traditional 12-stringed guitar and the sultry voices of the city’s best fado singers, or fadistas. Traditional fado conveys mourning and longing, or saudade, a feeling of loss often associated with the sea or the struggles of the poor. Its origins may stretch back centuries, though its history can only be traced to the 1820s. 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!

Accommodation: Heritage Avenida Liberdade Hotel, Lisbon
Included Meals: Breakfast, Dinner

After breakfast, you may depart at your leisure. But we recommend spending an additional day or two in this historic and endlessly fascinating city.

Included Meals: Breakfast


Linger Longer with a Tour Extension

Portugal: Porto to Lisbon 2

2020 Post-Tour Extension - Sintra & Pena Palace

  • Breakfast
  • City Information

1 Night From $398
per person, double occupancy

Single Supplement: From $198

Note: Day 1 of the Post-Tour Extension is the same day as Day 8 of the regular Portugal: Lisbon & Undiscovered Alentejo tour
After breakfast, you may depart at your leisure. But we recommend spending an additional day or two in this historic and endlessly fascinating city.

Overnight in Lisbon
Accommodation: Heritage Avenida Liberdade Hotel, Lisbon

Included Meals: Breakfast, Lunch

After breakfast, you may depart at your leisure.

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 transfers (Please note: If unable to walk, it is possible to transfer 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
Emergency travel assistance hotline available 24/7 Check
Access to Self-Guided Flight Concierge—Ask our knowledgeable team to find flights that sync perfectly with your planned trip. Check
Morocco: Marrakesh, Foothills of the High Atlas & Essaouira

Dates & Prices

2020 Dates Number of Travelers Pre Hotel Night Post Hotel Night
2-3 4+ Single Supplement
Solo Surcharge
2+ Single Supplement
2+ Single Supplement
Apr 30 - Jun 30 $4,248 $4,048 $898 $748 $248 $248 $248 $248
Sep 15 - Oct 31 $4,248 $4,248 $898 $748 $248 $248 $248 $248
Nov 1 - Nov 15 $4,048 $4,048 $898 $748 $248 $248 $248 $248
This tour is available on-request starting any day of the week except Friday*, from March 1 through June 30 and September 15 through November 15, 2020 (*due to the closure of the Arraiolos Tapestry Interpretive Center on Mondays). Please note that the tour price includes one arrival transfer from Lisbon to Marvão on Day 1 of the tour. If traveling in a group of two or more with separate arrival times, additional charges will apply for multiple transfers. All prices are per person, based on double occupancy.

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