Eastern Frontier


Take a north-south guided cycling holiday through some of the wildest and most beautiful countryside along the border between Portugal and Spain, exploring the ancient towns and landscapes of three different regions.

eet-01This is a fairly tough trip that will take in an incredible range of scenery as you join a small group (maximum 10 riders) bicycling south from the wild landscapes of the eastern Beiras, into the Spanish province of Extremadura and back into Portugal to cross the hills and plains of the Alentejo.

Starting from Guarda at the northern tip of the Serra da Estrela mountains, we ride through a rugged land of isolated villages, small towns, sweeping panoramas and some of the most dramatic castles in Portugal.

We will cross the border a few times and after an overnight stop in Extremadura, we cross the hills of the Serra de São Mamede before coming down into the more rolling landscape of the Alentejo, ending our tour on the southern plains in the historic town of Beja.

Scroll down to read more. You can also see what previous riders thought of this and other tours on our Reviews page. For further tour news and other information on biking in Portugal don’t forget to also check out the Pedal Portugal Facebook page and blog

“If you are looking to do a cycling trip through Portugal and are either a strong cyclist or looking for a trip that will test your mettle then sign up now. And as for Carolyn and Huw, they are the best! You honestly could not ask for better tour guides.” Mel Hurwitz, South Africa



All departures for 2018 are fully booked. We do not currently have any departures planned for 2019 but this may change – contact us at pedalportugal@gmail.com if interested.

Why this tour?

eastern-explorer-03The original idea behind this tour (previously called the Eastern Explorer) was for a north-south trip covering the length of Portugal.

However, to cycle the whole country in one go would have meant either riding long distances every day or taking much longer.

This tour provides a compromise: an opportunity to see some very different parts of Portugal – plus a little bit of Spain – while also having time to appreciate the scenery and explore some of the sights along the way. 

The Beiras region is one of the wildest parts of the country and sparsely populated but with some gorgeous scenery – plus several magical old frontier castles that look like they’re straight from the pages of a storybook.

The Alentejo is more rolling and its eastern expanses are also very quiet, with sleepy villages and hilltop towns set among a sun-baked panorama of open countryside and cork oak forests. The last part of the tour takes us out into the plains and wheat fields of the southern half of Portugal’s largest region.

This is quite a strenuous tour with nine days of riding, ranging in distance from about 64km (40 miles) to 85km (53 miles), and two optional rest days. While there are no major mountain ranges to cross, there are plenty of hills along the way, some of them quite tough.

Note: Riders must be reasonably fit and able to cycle 80-plus kms on consecutive days.

The distances given are generally the shortest options using good (low traffic) roads for cycling. 

None of the area explored by this tour is densely populated and the lack of people means most roads should be quiet – the only exceptions may be at harvest time or when forestry work is going on. We will also go through or around several wildlife/natural parks and birdwatchers can expect to be able to spot a variety of species, from bee-eaters to eagles.

Spring and autumn are the best times to see these regions – the northern Beira region can be cold and wet in the winter and the whole of Portugal can be way too hot in the summer for cycle touring. The landscape is a lot lusher in the spring, with wildflowers carpeting the countryside, but there’s a higher chance of rain. The autumn (fall) is generally a few degrees hotter.

Whichever month you pick, you should be able to expect lots of sunshine and plenty of warm (and hopefully dry) days. Average daytime temperatures in May/June are around 14-26°C (57-80°F) and in September are 16-27°C (61-81°F).

Note: Although the statistical average temperatures may sound pleasant, over the last two years afternoon highs in late September/early October have been 30-35ºC (86-95ºF) so riders need to be prepared for this kind of heat.

All pictures used on this page are of roads/locations featuring on the tour and taken on previous visits to the region.

Looking back towards the Serra de Estrela

Looking back towards the Serra de Estrela 

Where do we go?

The tour explores the eastern half of the huge Beiras region, skirting around Portugal’s highest mountain range, visiting some stunning castles along the way. One night is spent in Spain as we ride through an isolated area of Extremadura and cross the Tejo river.route overview

Continuing south through the Alentejo, the landscape is less wild but almost as quiet.

We will ride across areas of near-wilderness and rolling plains, sleep in villages overlooked by spectacular castles, and visit ancient towns dating to Roman times or earlier.

Although not car-free, the great majority of the route is on quiet lanes and back roads where traffic is very light.

There will be two rest days during the tour (with options for additional morning rides). Starting from Guarda the planned itinerary is as follows:

Eastern Explorer 02

  • Day One: arrive in Guarda by train and/or airport transfer and meet your fellow riders
  • Day Two: ride across wild and remote countryside and past some sleepy villages before crossing the Côa river and ending the day at the fortress town of Almeida – scene of an important seige in 1810. 63km
  • Day Three: we take some tiny little roads and visit the medieval walled village of Castelo Mendo before following the Côa south to the riverside town of Sabugal (with another castle). 74km
  • Day Four: We visit the small but picture-perfect castle at Sortelha before continuing south past Penamacor and on to stunning Monsanto, where the village is literally built into the granite boulders beneath a ruined fortress with stunning views. 72km
  • Day Five: spend the day cycling out to explore the countryside around Monsanto and visiting the ancient, near-abandoned former Roman city of Idanha-a-Velha – or take a rest day
  • Day Six: ride across a wide-open landscape of forested hills and rolling pastures, passing isolated villages before crossing the border into Spain and continuing to Alcántara with its crumbling old town of mansions topped by storks’ nests. 85km
  • Day Seven: we turn south-east and spend most of the day riding across the plains of Extremadura, crossing a couple of small ridges of hills before crossing back into Portugal and arriving at the one-time frontier border post of Marvão, where a 13th century castle perches atop a rocky ridge that offers amazing panoramic views of the surrounding countryside. 80km
  • Day Eight: entering the rolling landscape of the Alentejo, we ride to the historic fortress city of Elvas – staying in a converted military hospital/convent. 85km
  • Day Nine: go for a morning ride out from Elvas or explore the UNESCO-listed city’s fortifications – some of the best preserved military engineering of the 18th century. 
  • Day Ten: we turn west, following the Guadiana river, riding along little country roads towards the gorgeous hilltop village of Monsaraz. 72km
  • Day Eleven: ride south along the western side of the huge Alqueva reservoir, passing over the dam, on the way to the pretty provincial town of Moura with its old Moorish quarter – and the inevitable castle. 64km
  • Day Twelve: we continue a little further south through rolling country towards the historic town of Serpa before heading west and out onto the plains around Beja, the capital of the southern Alentejo and the end of our tour. 82km
  • Day Thirteen (Friday): say your farewells and transfer back to Lisbon

*Please note: the exact itinerary may change depending on accommodation availability and other similar factors.

“The Eastern Explorer Tour was a great trip made all the more enjoyable by our wonderful tour leaders.” Chris Cummuskey, Australia.

Eastern Explorer 04

How much?

The tour costs €1,560 per rider* – which works out at around £1,350 or $1,800 US (Nov 2017).
This includes:
  • 12 nights bed and breakfast (based on two people sharing a twin or double room) in a good hotel or guest house
  • evening meal – typically two or three courses with house wine or beer and coffee**
  • picnic lunch on main riding days (not provided on optional rides/rest days) 
  • support vehicle to carry luggage etc (and emergency transport)***
  • transfers from Lisbon or Porto to Guarda on Day One and to Lisbon on Day Thirteen if required****
  • experienced guide to ride with you*****


*Price: The price in euros will not change. However, as a UK-based operator, payment will be taken in sterling based on the exchange rate at the time.

**Food: Portugal is not great for vegetarians or anyone with special dietary requirements. I will try my best to make suitable arrangements but few Portuguese restaurants have vegetarian options. Please let us know about any dietary requirements and seek advice before booking.

***Support van: The support van will carry your luggage. It can also take passengers if a rider is unable to continue cycling following an accident, mechanical breakdown or other emergency. It is not suitable for using on a casual hop-on, hop-off basis and riders should be capable of riding the necessary distances on consecutive days.

****Transport & transfers: We will book train tickets between Lisbon or Porto and Guarda on Day One and from Beja back to Lisbon on Day Twelve if required. We can also advise on bus and/or rail travel for any riders travelling on other days or from/to different destinations.

*****Guides: My wife and I will alternate between riding with you and driving the support vehicle.

“The Eastern Explorer tour was just perfect! The cycling itself, the locations, accommodation, food & wine and Huw & Carolyn’s organization & logistics were wonderful. We could clearly feel the care & thoughtfulness which had gone into the planning & throughout the trip once we were on it.” Gayble Tsang, Hong Kong.

Heading from Monsanto towards Spain

Heading from Monsanto towards Spain

What’s not included?

The price above does not include:

  • travel to Portugal and any internal transport other than that detailed above
  • insurance – you are responsible for ensuring you have all appropriate insurance
  • lunch on Days 1, 4, 9 & 13*, snacks, coffees etc.
  • bike hire (see below)

*A picnic lunch will be provided on all main riding days. 

Wherever possible, if anyone is unable to ride I will try to take them in the support vehicle. However, the support vehicle is not intended for taking passengers. If essential, I can make arrangements with a taxi or bus but any individual costs will be additional.

Optional extras?

Cycle hire – road or hybrid bike – can be arranged but will cost extra. We work with Cycling Rentals, a company based near Lisbon which can deliver anywhere in Portugal.

Hiring a road touring or suspension touring bike for this tour will cost €190, including delivery and collection (not including any accessories). Prices of any other bicycle models will be confirmed at the time of booking. For more details, see bike hire page.

Single rooms should also be possible but this will involve an additional supplement of around €240. 

For anyone wanting additional accommodation, either before or after the tour, I can either book this for you or suggest various options but this would be an extra cost.

Supporting a worthy cause

We’ve both been long-term supporters of the disaster relief organisation ShelterBox and we donate £15 to the charity for every rider who joins this or any of our other tours.

What now?

Places are limited – and I need a minimum of six riders to make the tour viable – so the sooner you sign up the better.

If you have any questions, please feel free to contact me via pedalportugal@gmail.com

Otherwise, please read our full terms and conditions before completing the booking form.