History, nature and the peace of the Portuguese countryside come together when you’re Walking Medieval Alentejo.

Alentejo is often referred to as the breadbasket of Portugal, thanks to its advantageous climate and rich soils. Agriculture dominates day-to-day life across this sparsely populated landscape of arable farms, cork forests and sleepy rural villages, but it’s also a region with a rich and colourful history. The first settlements date back to 5000 BC and Alentejo is home to many of Europe’s most-important megalithic sites – the Romans came next, drawn by the region’s rich natural resources, as were the Visigoths and the Moors who followed. The crusading Dom Afonso Henrique arrived in the 12th century and the formation of the Kingdom of Portugal followed.

Afonso’s descendant, the 13th century ruler Dom Dinis, understood the military significance of the region and set about reinforcing Portugal’s eastern border against his hostile Castilian neighbours. Your holiday begins in Castelo de Vide, considered one of the best-preserved medieval hilltop towns from this period. Plain old ‘Vide’ was rechristened Castelo da Vide when Dinis rebuilt its existing Moorish castle and fortified the city’s walls. The town saw a period of rapid expansion as agricultural workers were drawn in from the surrounding flatlands to the safety the castle provided. Now referred to as Vida’s old quarter, you’ll have a chance to explore this medieval maze of narrow, twisting lanes and cobbled alleyways.

Rampaging Castilian’s aren’t so much of a problem these days, and the meandering waymarked trails of the Parque de Merendas and the Coureleiros Megalithic Park will lead you through a tranquil landscape of hardy Pyrenean oaks, snub chestnut trees and cultivated olive groves.

Leaving Vide, you’ll head up to your new accommodation in the medieval village of Marvao. Sitting on a 900m high granite escarpment, Marvao’s purpose was also military: a hilltop lookout with a panoramic view across plains of the Rio Sever – another of Portugal’s vulnerable borders. To modern eyes, it’s a pretty, fairytale location which wouldn’t look out of place in an episode of Game of Thrones, and is becoming increasingly popular with day-trippers in the summer months.

A stay in Marvao is the only true way to experience life in such a beautifully preserved medieval village. Spring is ideal when the walking trails around Galegos and Portagem are surrounded by a sea of wild flowers and cherry blossoms. Autumn’s also a lovely time to visit – particularly during the chestnut harvest. Like her wines, Portugal’s chestnut crops are subject to Denominacao de Origem Controlada and Alentejo’s magusto chestnut festivals are a wonderful culinary celebration of one of the country’s best-loved seasonal staples.


You’ll begin your holiday with a direct flight to Lisbon. Our driver will collect you from your flight, for your (twenty-minute) transfer into the centre of the city, and we’ll provide you with a handy online guide to the best restaurants in Lisbon.
Our driver will collect you from your hotel for the drive from Lisbon to your new accommodation in Castelo de Vide. Nestled in the foothills of the Serra de Sao Mamede mountains, Castelo de Vide is considered one of the best-preserved medieval hilltop towns in Portugal.
For your first walk, you’ll follow a circular route through the Parque de Merendas, following an ancient, cobbled path onto the Serra de Sao Paulo, (distance: 10km, ascent: 300m, difficulty: easy to moderate).
Our driver will transfer you to Meada for today’s walk, which takes you via the Menhir of Meada and the Coureleiros Megalithic Park: two of Europe’s most-important prehistoric sites, (distance: 10km, ascent: 300m, difficulty: easy to moderate).
You’ll leave Castelo de Vide today, walking south to your new accommodation in the hilltop town of Marvao, (distance: 11km, ascent: 500m, difficulty: easy).
You’ll walk the trail from the small olive-oil producing town of Galegos to Marvao, (distance: 9km, ascent: 780m, difficulty: easy to moderate), with an afternoon free to explore the medieval Castelo de Marvao.
For your final full day, you’ll walk from Marvao down to Portagem and back again, via the Ponte Romana da Portagem, (distance: 13km, ascent: 400m, difficulty: easy).
You'll be transferred to Lisbon airport for your flight home.

From £2000 per person

We can create a tailor-made holiday to suit your budget.

Direct flights from the UK to Lisbon, accommodation in twin/double en-suite rooms on a B&B basis, airport transfers, luggage transfers between hotels, digital route maps and restaurant recommendations.


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