Portugal Private Journey

Hiking the Hidden Towns of Alentejo


With walled hilltop villages crowned by ancient castles, whitewashed houses gleaming in the sun, extraordinary megalithic monuments including stone circles, and the legacies of the Romans and Moors, the Alentejo is a captivating part of Portugal—and still relatively undiscovered. On this Private Journey, you’ll walk historic paths from one village to the next, soak up the atmospheric past as you explore Roman monuments and the evocative remains of Moorish castles, and visit award-winning wineries and even a gin distillery (with tastings, of course!). Many of the hikes begin or end right at your hotel, and they are flexible in length (your choice). Most of the accommodations are in lovely pousadas, traditional or historic properties that help tell the story of Portugal’s past. Throughout the journey, you’ll sample the traditional local dishes of Alentejo, one of the most distinctive regional cuisines in all Portugal. Add-on options include a cooking class and a visit to a pottery workshop where you’ll have the opportunity to paint your own tile.

Itinerary at a Glance

Days 1-3
Lisbon / Tagus River Cruise / Marvão / Castle-to-Castle Walk

After exploring Lisbon, head into the countryside for a short cruise on the Tagus River, a visit of Belver’s 12th century castle and megalithic dolmen, and a castle-to-castle walk from Marvão to Castelo de Vide, a delightful spa town whose springs were once enjoyed by the Romans and Moors. Castelo de Vide has an interesting Jewish heritage—in the Judiaria (Jewish quarter) a 13th century synagogue is hidden among the cobbled alleys. 

Pousada de Lisboa
Lisbon, Portugal
Day 1 (1 night)
Pousada do Marvão
Marvão, Portugal
Days 2 to 3 (2 nights)
Days 4-5
Portagem / Évora / Convento do Espinheiro

Hikes lead along a historic trail used by Jewish refugees fleeing the Spanish Inquisition, and along a 16th century aqueduct that once brought water to the town of Évora. Soak up the past while viewing the Almendres Cromlech, a prehistoric site dating back to the 6th millennium BC, go on a walking tour of enchanting Évora, a World Heritage Site, and enjoy wine tasting and an optional class in Alentejo cuisine at your hotel, Convento do Espinheiro, a former convent.

Convento do Espinheiro
Évora, Portugal
Days 4 to 5 (2 nights)
Days 6-7
Roman Villa of Tourega / Monsaraz / Minas de São Domingos

After exploring the ruins of the ancient Roman villa of Tourega, visit the tiny walled town of Monsaraz with its requisite castle (its inner courtyard is now a bullring), and taste the wares at the local gin distillery. The next day, head out on a hiking trail that was once a rail line for the local gold and silver mines, at one time the largest in Portugal, and take to the Guadiana River for a relaxing boat ride, or for something more active, a kayaking tour.

Alentejo Star Hotel
Minas de São Domingos, Portugal
Days 6 to 7 (2 nights)
Days 8-10
Setúbal / Palmela / Arrábida Natural Park

Arriving at the coast, explore Setúbal’s pedestrian-only city center, hike an ancient path right to your hotel in the Castelo de Palmela, set on a hilltop with commanding views, and follow a coastal trail in Arrábida Natural Park for beautiful views of the sea. One afternoon, choose between meeting a local artisan for a pottery workshop and enjoying one last wine tasting! Depart on Day 10 via Lisbon.

Pousada Castelo Palmela
Palmela, Portugal
Days 8 to 9 (2 nights)


  • Cooking class in Alentejo cuisine
  • Visit to a pottery workshop for an opportunity to paint your own tile



Walk historic trails between ancient hilltop villages
Enjoy wine tastings and a fun cooking class in local Alentejo cuisine
Explore Évora, a UNESCO World Heritage Site, with its prehistoric sites and Roman ruins
Visit Marvão, a well preserved medieval village with sweeping views of the Alentejo plains
Walk a cliffside coastal trail Arrábida Natural Park


Length: 10 days
Cost From: TBA  
Arrive: Lisbon, Portugal
Depart: Lisbon, Portugal
Lodging: 9 nights pousadas and hotels
Meals: All meals included except 5 lunches and 5 dinners as indicated in the Detailed Itinerary (B=Breakfast, L=Lunch, D=Dinner)
Activity: Hiking / Trekking
Trip Level:

Easy to moderate hikes, 2-3 hours, with longer options, walking tours, van support (for luggage or if you wish to skip a day's hike)
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