Eastern Frontier Tour


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 four different regions.

eet-01This is a fairly tough trip that will take in an incredible range of scenery as you join a small group bicycling south from the wild landscapes of the eastern Beiras, into Extremadura (Spain), across the hills and plains of the Alentejo and all the way down to the Gulf of Cadiz.

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.

After a detour into the Spanish province of Extremadura, we cross back into the wide open expanses of the Alentejo and its historic towns before heading on through the Algarve hills and winding our way down to Portugal’s far south-east.

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



Planned departure/finish dates for the Eastern Frontier Tour are:

  • September/October 2017: Sunday 24th Sept – Friday 6th Oct Tour full – booking closed
  • May 2018: Sunday 20th – Friday 1st June
  • September/October 2018: Saturday 22nd – Thursday 4th Oct Two places remaining

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 three 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 heads through the hills of the inland Algarve, following the Rio Guadiana for part of the way, until reaching journey’s end at Vila Real de Santo António and the coast of the Gulf of Cadiz. 

This is quite a strenuous tour with nine days of riding, ranging in distance from 60km (37 miles) to 83km (52 miles), and two 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 the shortest options that take good roads for cycling. For groups happy to ride longer distances it will be possible to extend all or some of the days to cover more ground.

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 Beira Alta can be cold and wet in the winter and all three areas get uncomfortably hot in the summer. 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 also 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 with average daytime temperatures in May/June of around 14-26°C (57-80°F) and in September of 16-27°C (61-81°F).

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.East Exp route

Continuing south through the Alentejo, the landscape is not so wild but is almost as quiet. The last section in the Algarve gets hillier as we work our way down to the point where Portugal’s south coast meets the Spanish border.

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 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 through the foothills of the Serra da Estrela before turning east to the pretty little town of Belmonte. We then visit the spectacular castle at Sortelha before continuing to the riverside town of Sabugal. 67km
  • Day Three: ride south, skirting the Serra da Malcata nature reserve and visiting the medieval castle at Penamacor before continuing to the stunning setting of Monsanto, where a picturesque village huddles beneath yet another ruined granite fortress. 60km
  • Day Four: 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 Five: 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 Six: 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 Seven: 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 Eight: we cross a small range of hills and ride past a 14th century convent (now a luxury hotel) before continuing on quiet roads to the picture-perfect hilltop village of Monsaraz. 72km
  • Day Nine: explore the countryside and villages around Monsaraz – or spend a rest day in this idyllic spot
  • Day Ten: 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 attractive pedestrianised centre – and inevitable castle. 64km
  • Day Eleven: the countryside starts to get a little wilder as we ride to the walled town of Serpa and then into the Guadiana Valley natural park on our way to the ancient river port of Mertola. 83km
  • Day Twelve: the terrain becomes more rugged as we ride into the hills of the inland Algarve, following the banks of the Guadiana for a while before heading back into the hills and descending to Vila Real de Santo António and the end of our tour. 82km
  • Day Thirteen (Friday): say your farewells and transfer to Faro

*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 €1,355 per rider* – which works out at around £1,155 or $1,500 US at current exchange rates (July 2016).
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 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)***
  • transport from Lisbon or Porto to Guarda on Day One if required****
  • transfer to Faro 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 may be able to offer a pick-up service from Lisbon but this will depend on numbers and arrival times. If this is not practical for any reason we can book train/bus tickets to Guarda from either Lisbon or Porto. We will also offer transfers to Faro on Day Thirteen, which can be to either the city’s airport or the mainline railway station. 

*****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 that is based near Lisbon but can deliver anywhere in Portugal. The exact cost will vary depending on the type of bike, any accessories required and the number of people hiring. However, the cost for a road touring bike/hybrid suspension touring bike, including delivery/collection but not any accessories, will be around €190-200 for the duration of the tour.

Single rooms should also be possible but this will involve an additional supplement of around €220-240 (exact price will depend on numbers/month). 

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.