Alentejo walking holiday in Portugal

Self-guided walking along an exclusive route over medieval pathways and stunning coastal trails through the Alentejo region.
Self-guided walking in Alentejo Stay in family-run guesthouses Full support including detailed maps, route notes, GPS and luggage transfer Lisbon Marvao Castelo de Vide Evora Iron Age monuments and a Roman temple Follow a section of the 'Fishermen's Trail' Costa Vincentina See the only sea cliff stork nests in the world
£1480 excluding flights
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8 Days
Tailor made
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Price per person based on two sharing, includes accommodation, luggage transfers, welcome briefing, walking notes and maps and meals as noted.
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Description of Alentejo walking holiday in Portugal

Walk our exclusive route from the Spanish border to the dramatic coast of Portugal's little-visited Alentejo region. By thoughtfully linking together medieval pathways, coastal trails and family-run guesthouses, this trip gets right to the heart of the varied beauty and cultural heritage of Southern Portugal. Small parts of the trip are done by road, skipping out the less interesting parts and allowing you to traverse the country from east to west.

Hilltop villages and ancient castles provide insights into life in rural Portugal, both now and many centuries ago during times of conflict with its Spanish neighbours. The Mediterranean cork and holm oak forests of the distinctive Montado landscape give way the golden beaches and dramatic coves of the Costa Vincentina as you reach the Atlantic sea.

Throughout the walk you are fully supported, starting with a welcome briefing and our detailed walking notes and maps. You have a GPS device and the peace of mind of our 24 hour local telephone support should you need it.

In Évora you have a local guide to lead you through the many layers of history of the town and the region. Road transfers are guided too, so at every stage you have a real connection to the local way of life and a deeper understanding of the link between the landscape and the people.

Price information

£1480 excluding flights
Convert currency:
Price per person based on two sharing, includes accommodation, luggage transfers, welcome briefing, walking notes and maps and meals as noted.
Make enquiry

Departure information

Departs on a date to suit you from March to June and September to November. However, please note the holiday cannot start on a Monday.

Travel guides

Portugal walking
Forget the golf courses and beach resorts. Give the Algarve the elbow. Portugal is much more than a summer holiday hotspot and there’s no finer way to...
Likened sometimes to Tuscany or Provence, Portugal’s Alentejo is actually a little more rustic and a lot less visited than France or Italy’s celebrate...

Responsible Travel

As the pioneers of responsible tourism, we've screened this (and every) holiday so that you can travel knowing it will help support the places and people that you visit, and the planet. Read how below.


One hotel used in the itinerary is run by one of Portugal's most renowned environmental and wildlife conservationists. The two-story farm is located in expansive grounds which provide a habitat for over 150 different bird species and 23 different kinds of amphibians.

The pousada in which you stay in Marvao is a joining together of two medieval buildings, features of which date back as far as the 13th century. Similarly, the hotel in which you stay in Castelo de Vide is a grand house from the 18th century, now protected as a Monument of Public Interest.

Each walk is regularly checked by our team to ensure both accuracy and the preservation of the environment. Detailed walking notes are provided to ensure that walkers do not encroach upon the protected land, following established trails. Thoughtfully engaging with the landscape is ultimately the best way to value and protect it for future generations.

One of our key partners is a wine and food producing farm in the heart of the rural Alentejo landscape. The farm uses modern agricultural techniques to protect and preserve the land, returning it to its original purpose, which dates back to Roman times. The estate supports olive groves, cork oak forests and lakes which welcome a range of migratory birds.


Throughout the trip we work directly with guides, drivers, small family-run guesthouses and restaurants to ensure that your visit directly benefits the local community, both economically and in the preservation of distinct local culture and ways of life. The hotel in Castelo de Vide for example is a family business, now in its fourth generation of owners and very much integrated into the community.

This Inn to Inn trip is primarily self-guided, following walking notes and maps. However you are taken by road in some of the places, facilitating your trip from the mountains near the Spanish border to the Atlantic sea. These are guided transfers, ensuring that you have a closer connection to the country at every stage of the journey. It is important to us that you leave with a sense of how people live in the Alentejo region and the history of the area.

The first hotel of the itinerary is built around a restored abandoned train station, with many of the original features having been carefully restored. This has given a new lease of life to a beautiful part of the region's cultural heritage. An important facet of the work undertaken by the Herdade do Freixo this is the promotion of local vini and agri-culture.

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