Headwater – Self-Guided Cycling in the Douro Valley

from $1,899.00

Enjoy historical villages, the River Douro and some of the world’s finest

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  • Vacation Style Holiday Type
  • Activity Level Moderate / Challenging
All about the Headwater – Self-Guided Cycling in the Douro Valley.

This cycling holiday in the Douro will acquaint you with fascinating and magical surroundings, delicious cuisine and some of the world’s finest wines (including, of course Port Wine, for which the region is famous). The ride begins in Castelo Rodrigo, a medieval village close to where Portugal borders Spain, and home to an ancient castle and arched palace gates. Your cycling heads across the highland plain to the Spanish border and on through historical villages to the River Douro. You’ll cycle through uniquely terraced vineyards and take in the typical towns and villages of the region, including Pinhao, where many of the famous Port wine estates are located. The accommodation is all chosen with the greatest care and you’ll stay in different types, from delightful rural houses to 3 and 4 star hotels.

The tour package inclusions and exclusions at a glance
What is included in this tour?Items that are included in the cost of tour price.

* All breakfasts and 1 dinners
* 5 nights in hotels, guesthouses and rural tourism houses (see
accommodation section)
* Luggage transfers
* Local bike hire

  1. Day 1 Start Porto airport; transfer approx. 3 hours to Castelo Rodrigo, not far from the Spanish border.

    Pick up a shared transfer from Porto airport (included) to the easternmost point of your holiday; Castelo Rodrigo. Enjoy the beautiful landscape and scenery that unfolds along the way, entering the fascinating landscape of the Douro River Canyon and its 200 metre high cliffs. The historical village of Castelo Rodrigo deserves an exploratory walk, with its cobbled streets, palace ruins, old walls and ogival arched gates, 16th century pillory and medieval church. Your hotel is located in Castelo Rodrigo with great views over the surrounding plains, mountains and all the way to the border with Spain.

  2. Day 2 Cycle across high plains to Almeida and Escarigo on the Spanish border

    The first day of cycling takes you across high plains to the historical village of Almeida, one of the most important strongholds in Portugal’s history. Although it had been occupied by humans since the Palaeolithic era, it was only during the Arabic period that the name of the village came about – Al Meda meaning “the table”. There is an ancient tale that a sumptuous table embedded with precious stones once stood in this spot. However, Almeida’s military importance was yet to come…taken and re-taken many times during battles between the Portuguese and the Castilians, in 1296 a new castle was built by the Portuguese, then in 1640 an enormous star-shaped fortress was built around the town to defend against Spanish and French attacks. Eventually falling to Napoleon’s armies it was later used by the Portuguese as a political prison. Also visit the village of Vilar Torpim, with it’s chapel and manor house, and Escarigo, right on the Spanish border. Return to Castelo Rodrigo for your overnight.

  3. Day 3 Cycle to Aldeia do Juízo along backroads with beautiful landscapes

    At the beginning of the day, cycle around the Serra da Marofa mountain range. Experience stunning views over the Iberian Plateau and from the top you can also see the Douro river system (which, beyond this river, includes Côa and Águeda rivers), to the East. Continue on to Aldeia do Juizo, a rural village with 2 chapels, several wineries and a community oven that is surrounded by vineyards, olive groves and almond orchards. On the banks of the river, there are vegetable-gardens, where the locals produce a wide variety of agricultural products. Stay in a delightful village house, part of a rural tourism complex of restored houses, all with private bathroom facilities.

  4. Day 4 Cycle through the historical villages of Marialva, Meda and on to Penedono

    On the ride today you cycle through two historical villages, Marialva and Meda before your approach to Penedono, with views of its almost hexagon castle, perched on an outcrop. After the first 10 km you will be able to see the Castle of Marialva. When you reach the village, explore the streets, lined with buildings that have stood the test of time and which lead to the citadel surrounded by ancient walls. The next highlight is Meda – in medieval times this village was essentially a border town and the setting for hard-fought skirmishes between Christians and Muslims. The watchtower was one of the most important strategic defence points in the region and combined with the castles of Marialva and Longroiva. Today the village is quiet and the main activity is farming and wine-making. Continue on to Penedono and its medieval castle, a unique example of military architecture that dominates the surrounding countryside.

  5. Day 5  Ride to the UNESCO World Heritage listed vineyards of the Douro Valley

    The Alto Douro winemaking region is most famous for its Port wine, but the region also produces world-famous wines from the Touriga grape. The terraced vineyards are so typical of the region that they are listed a UNESCO World Heritage site and are a delight to behold. The neatly-kept wine estates rise proudly amidst the vineyards, their names clearly visible to everyone who passes. In the afternoon enjoy a boat trip on a ‘Rabelo’, a traditional ‘gondola-shaped’ boat that in earlier days transported up to 50 barrels of wine at a time, downriver, to Porto. The Port wine town of Pinhao is your next stop, with it’s exquisite train station, the ceiling covered in azulejos (traditional Protuguese blue ceramic tiles). You spend the night in Pinhao.

  6. Day 6 Enjoy the final cycling day along the Douro River, arriving in Peso da Regua: the International Capital of Wine and Vineyards.

    The route today will first take you along the magnificent Douro Valley, along the riverside, then inland to Tabuaco. The views are nothing less than breathtaking, as if the Douro Valley is ensuring that you will never forget its magical beauty. Head back down to the riverside and enjoy a guided visit and wine tasting at Quinta do Tedo, an 18th century estate at the confluence of the Douro and Tedo rivers. At the end of today’s cycle you will arrive in Peso da Regua; the ‘International Capital of Wine and Vineyards’, at the centre of the Port wine-growing region and historically important for being the world’s first ever region specifically demarcated for wine production. 

  7. Day 7 Transfer back to the airport, or choose to spend extra time in the cosmopolitan city of Porto. 

    This morning you check out from your hotel and are transferred back to Porto; here you can choose to spend some time in this cosmopolitan city, or go straight back to the airport for your flight home. Extra nights in Porto can be requested at the time of booking.

Package Confirmed Dates Trip Status Trip Status Price (PP) Excluding Flights Price (PP) Including Flights  
October 5, 2019
October 12, 2019
October 19, 2019
October 26, 2019