Alentejo Castles and Wine Cycling Tour

Day 1: Arrival in Arraiolos
You will arrive in the medieval village of Arraiolos, famous for its castle and embroidered rugs. After checking in, you can relax by the pool or wander its picturesque streets. At 5 PM a welcome drink and briefing with our local guides will give you an overview of the routes ahead.

Day 2: Arraiolos – Évora (30 or 43 km; +360 m)
You will ride through the whitewashed lanes of Arraiolos, learn about its centuries-old weaving tradition and taste the local sweet, Pastéis de Toucinho. A climb to Arraiolos Castle, one of the few round castles on the Iberian Peninsula, rewards you with wide views over the Alentejo plains. Rolling countryside, olive groves and vineyards will carry you on to Fita Preta Winery, set in a restored 14th-century palace, for a tasting of award-winning wines; an aromatic herbs farm with teas, honey and olive oil is the alternative. The stage is 30 km if you sleep in Évora, 43 km if you stay at the countryside guesthouse Monte do Serrado de Baixo.

Day 3: Évora and the Megalithic Route (46 or 72 km; +400 m)
You will start in Évora, a UNESCO World Heritage Site, with its Bones Chapel and 13th-century cathedral, and a wine tasting at the Évora Wine Tour Shop. Then you will ride into the countryside, through holm oak forests and open meadows with grazing cattle and birdsong, to some of Europe's most impressive megalithic sites: Zambujeiros' Dolmen, the Almendres Cromelech and Menhir, and Mitras' Church. With the transfer back the day is 46 km; cycling from the farm and back it is 72 km, mostly on gentle rolling dirt roads.

Day 4: Évora – Reguengos de Monsaraz (50 or 59 km; +210 m)
A peaceful cycling lane will lead you through the quiet Alentejo countryside, past small villages and spots for a picnic. In Nossa Srª de Machede you will meet a local leather artisan, then continue to Valongo Castle, rich with Roman history. From there you can choose the local ecotrail, the asphalt road or a dirt track, and wine lovers can stop at Adega José de Sousa, where wine is still aged in clay pots.

Day 5: Reguengos de Monsaraz – Monsaraz (31 km; +330 m)
You will pass through S. Pedro do Corval, where local artisans craft and paint clay pots, and ride on to the Alqueva dam reservoir, the largest artificial lake in Europe, for a scenic lunch. The day ends with the climb to the fortified village of Monsaraz, a historic stronghold on the border with Spain, and its castle, with views over the countryside and the medieval village below.

Day 6: Monsaraz – Vila Viçosa (60 km; +560 m)
Today you will ride to Vila Viçosa, the marble capital of Portugal, where the so-called "white gold" shapes wide streets and grand buildings. After a picnic lunch you will visit an impressive fortified sanctuary with a fascinating story and see the distinctively colored lagoons, before reaching your accommodation in an elegant, aristocratic setting.

Day 7: Vila Viçosa – Estremoz (33 km; +275 m)
A gentle stage will leave time to stop at taverns for Petiscos, the local snacks, and to visit the Ducal Palace of Vila Viçosa and the marble museum. As you approach Estremoz, the marble architecture marks the final stretch of the journey. You will finish with a climb to the marble Donjon tower of Estremoz castle, where you will spend the night.

Day 8: Departure from Estremoz
After breakfast your Alentejo cycling journey comes to an end. A transfer to the airport can be booked as a supplement.