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Portugal’s Castles and Wine

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Homepage > Portugal > Portugal’s Castles and Wine
  • Duration: 7 Nights
  • Difficulty: Level 2
  • Tour Type: Self Guided
  • Availability: Saturdays March to November (other days with a supplement)
  • Location: Arraiolos

Castles and Wine

Tour Details

Welcome to Hooked on Cycling Holidays and our beautiful self-guided cycling holidays in Portugal. Our bike vacations are based in the unexplored region of Alentejo midway between Faro and Lisbon. This region takes you away from the tourists’ region of the Algarve and into the stunning countryside and coastal scenery. This is a cycle tour is a combination of cycling and discovery, you can be sure to leave Portugal with a much richer knowledge of our region!

On your bike rides you will visit castles, churches, artisans, vineyards and typical family-owned cafés. The landscape changes from olive groves to vineyards and cork oaks, from granite to schist and to marble. The accommodation is mostly in renovated palaces, convents, castles or lovely farms. Roads are mostly undulating. This means that you rarely have big climbs, but go slightly up and down several times. We mix some dirt roads with asphalt, but most of the tour is on asphalt. The dirt road connections give the tour a special link to nature.

Starting Location


Price Includes

  • 7 Nights Bed and Breakfast
  • 3 /4 star accommodation
  • Information Pack
  • Route Instructions
  • Luggage transfers

Price Excludes

  • Transport before and after tour
  • Flights
  • Travel Insurance
  • Hybrid Rental Bike
  • Extra Nights
  • Airport transfers
  • Season supplement
  • Non Saturday departure
Trip Info

Travel Insurance

It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.


Day 1Arrival to Arraiolos

Arrival and make your way to Arraiolos. Arraiolos is a wonderful medieval village with a beautiful castle.

Day 2Arraiolos to Évora 18-28 miles 30-45 km.

Today you start riding through the village of Arraiolos which is famous for its pastries and carpets! It has a historic centre which is well worth exploring. Visit the castle dating from 1305 when King Dinis decided to build the huge fortress. The castle has an external wall of 455m and is 2 metres thick and is one of the few rounds shaped in the peninsula.  From its wall, you will see incredible views all around you.

Now cycling along minor undulating roads we reach a cheese farm, where the farm also produces local liqueurs. Further along, we shall come across a vineyard which has an unusual private collection of carriages. Here if you wish you could stop for a break and lunch. We continue later in the afternoon towards Aldeia da Terra and on via a disused railway line called the eco-trail which is traffic-free, into Evora your destination.

Day 3Megalithic Route – cycling around Évora 28 miles 45km

Today you´ll visit while cycling some of the most important megalithic monuments of the region. Some of the Neolithic constructions you might see as puzzling and are dated almost from 5000 years ago. Apart from this, you shall be cycling through a pretty landscape with holm oak and cork trees. The ride will finish back in Evora when you should spend the time to explore the streets and get immersed in the ancient pre-roman settlement. The 13th-century bone chapel is a must to see as one of the highlights of the town.

Day 4The Valley of the Degebe River cycling from Évora to Reguengos de Monsaraz 31-36 miles 50-57 km

You ride between olive groves to reach the small and traditional village of Nossa Srª de Machede. Here you should stop at a local café for a drink, visit the leather factory and an olive mill (when in season). Then you will pass the Castle of Valongo and visit a cheese factory in Aldeias de Montoito. Arriving at Reguengos de Monsaraz you still have plenty of time for some wine tasting in a gorgeous winery where they still have a room with the old clay pots to keep the wine.

Day 5Conquest of the Castle of Monsaraz Cycling from Reguengos to Monsaraz 19 miles 35 km.

You can visit the famous pottery village of S. Pedro do Corval, where you can see the men working the clay, transforming it into beautiful pots and plates, and the ladies painting them with flowers. We recommend that you have lunch by the lake (take a picnic), with a beautiful view over Monsaraz. Then it is time to conquer the gorgeous village of Monsaraz, built in a castle on top of a hill. From Monsaraz you’ll take in the beautiful view over the lake of the Alqueva dam, the biggest artificial lake in Europe.

Day 6 The Sanctuary Route Cycling from Monsaraz to Vila Viçosa 30 miles 50 km.

Today you leave the schist land and discover the marble kingdom. Start with a gentle rolling morning ride and then visit the impressive sanctuary of Nossa Srª da Boa Nova and the flowery village of Terena. After comes the moon-like landscape of the marble quarries of Bencatel area. From here the «white gold» was extracted to build gorgeous cities such as Estremoz and Borba. We arrive at Vila Viçosa, a favourite resting place for many kings who were followed by many noble people who built beautiful manor houses in the area.

Day 7The Marble Route cycling from Vila Viçosa to Estemoz 19 miles 35 km

You start by visiting the fabulous Ducal Palace of Vila Viçosa and then follow to Borba. In Borba, you can visit one of those typical local cafés where the wine served is produced at the clay pots that decorate the space. It’s the local «handmade wine». You visit a marble quarry and then follow to the Church of Nossa Srª dos Martires, a marble gothic church. Arriving at Estremoz you’ll be impressed by the beautiful architecture and the imposing tower of the castle where you will sleep!

Day 8Departure

Depart after breakfast.


How to get there

To Lisbon airport where you travel by bus to Arraiolos or book a return private transfer.  Only a few buses per day currently at 3pm and 5pm (subject to change)

Book Now

2024 Prices – For a complete tour price breakdown please click the book now button and select your holiday tour date. Prices will then be listed.

 Tour Code Prices From (per person) Book Now
Portugal Saturday (7 Nights) from £1167 Book Now
Portugal Non Saturday (7 Nights)  from £1267 Book Now
Tour Images
Cyclist on a dirt path in Portugal