Eastern Frontier

12-DAY TRIP/10 DAYS OF CYCLING – from €1,775

Take a guided bike tour through some of the wildest and most beautiful countryside on the border between Portugal and Spain, exploring ancient towns, frontier forts and rugged landscapes.

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Wild landscapes and empty roads in the eastern Beira region

This is our toughest tour and not for inexperienced riders as it requires being able to cycle around 80km (50 miles) on consecutive days. Although there are no major mountains, some days also involve considerable amounts of climbing. (See the itinerary below for more details.) Heat can also be a significant issue.

On the other hand, we don’t rush the ride as this bike trip will take you via some of the most beautiful scenery and quietest roads to be found anywhere in Portugal, taking in isolated villages, picturesque swimming holes, dramatic castles and sweeping panoramas.

Our emphasis is always on taking time to enjoy the cycling and the sights along the way, rather than racing to get from point to point.

“The best value for your dollar of any bike trip I have done.” Jill Hill, Canada.

Afternoon light on the frontier castle of Marvao

Biking in a small group, we will take you through the wild landscapes of the eastern Beiras, up to the Douro valley, and then south through some of the remotest parts of Portugal.

We cross the border into Extremadura, crossing the river Tejo on a spectacular Roman bridge, and spend one night in Spain.

After crossing back into Portugal through the hills of the Serra de São Mamede we come down into the more rolling landscape of the Alentejo, ending our tour at the UNESCO-listed fortress town of Elvas.

“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



Departure/finish dates for this tour are:

  • 2023: Saturday 7th to Wednesday 18th October – €1,775 – Sorry – tour full

Why this tour?


This tour provides the chance to get off the beaten track and see some parts of Portugal few other tourists visit – plus one night in a small Spanish town.

The eastern half of Portugal’s 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.

Spain’s Extremadura provides a real contrast – wide, open expanses stretching into the distance, with vultures often soaring overhead! 

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.

Most of the area explored by this tour is very sparsely 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 and vultures.

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 much 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, afternoon highs in late September/early October have often reached 30-35ºC (86-95ºF) over the past three years so riders need to be prepared for this kind of heat.

Looking back towards the Serra de Estrela
Looking towards the Serra da Estrela 

Where do we go?

The tour explores the eastern half of the huge Beira region. Starting from Portugal’s highest city, we head north initially towards the Douro valley before turning south and roughly following the border with Spain.

We ride through wild hill country, remote countryside and isolated villages, visiting some stunning castles and fortresses before crossing the border into Spain.

After crossing back into Portugal, we continue south through the Alentejo, where the landscape is not quite as wild and rugged 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.

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

There will be two rest days during the tour (with options for additional morning rides). Starting from Guarda the planned itinerary for 2020 is as follows:

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  • Day One: arrive in Guarda by train or bus and meet your fellow riders
  • Day Two: head around the northern end of Portugal’s highest mountains – the Serra de Estrella – and on via Trancoso, a walled town given its charter by the first king of Portugal, to a rural manor house for our first night on the road. 68km / 1,072m ascent
  • Day Three: continue north via the lovely village of Penedono with its unusual triangular castle and on to rural hotel on the edge of a remote area known for its prehistoric rock carvings. 58km / 816m
  • Day Four: After reaching the banks of the Douro river, we turn south through more wild and remote countryside, ending the day in the small town of Figueira de Castelo Rodrigo. 77km / 838m
  • Day Five: take a rest day, with options to explore the ruined medieval castle above town and the Peninsular War-era fortifications at nearby Almeida.
  • Day Six: we take some tiny little roads and visit a couple of historic villages – including the Duke of Wellington’s winter HQ from the Peninsular War – before stopping in a small spa hotel near the banks of the Côa river. 77km / 838m
  • Day Seven: We continue south through a mix of wild hills and quiet countryside to stunning Monsanto, where the hilltop village is literally built into granite boulders beneath a ruined fortress with stunning views. 81km / 1,046m
  • Day Eight: It’s a short hop today, via a swimming spot tucked into some granite hills, to a laid-back little hotel just metres from the Spanish border. 26km/174m
  • Day Nine: after following some tiny country roads through the Portuguese countryside, we cross the border into the Extremadura region of Spain. After crossing the Tejo river on an ancient Roman bridge, we spend the night in a former convent in the Spanish town of Alcántara. 57km / 841m
  • Day 10: we continue across the open landscapes of Extremadura before crossing back into Portugal on the edge of the Serra de São Mamede natural park and a final climb to the spectacular hilltop village of Marvão, where we stay a stone’s throw from a 13th century castle with fabulous panoramic views. 81km / 1,250m
  • Day 11: continuing south into the rolling landscape of the Alentejo, we ride to Elvas – where we end our tour at a converted military hospital/convent in this UNESCO-listed city ringed with 18th century fortifications. 81km / 804m
  • Day 12: say your farewells and transfer back to Lisbon

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

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

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How much?

The tour costs €1,545 per rider for September 2021. This includes:
  • 11 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 12 if required***
  • experienced guide to ride with you****


*Food: Vegetarian and other special diets are possible but need to be arranged in advance – and menu choices may be less varied. Please let us know about any dietary requirements and seek advice when 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 or bus tickets between Lisbon or Porto and Guarda on Day One and from Elvas back to Lisbon on Day 12 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 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

Looking down into the Douro valley

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
  • snacks, coffees and lunch on non-riding days
  • bike hire (see below)
  • single rooms (see below)

If anyone is unable to ride, where possible, we will try to take them in the support vehicle. However, the support vehicle is not intended for taking passengers. In some circumstances, we may need to make arrangements with a taxi or bus but any individual costs will be additional.

Cycle hire

For anyone wanting to hire a bike, we work with Cycling Rentals, a company based near Lisbon that can deliver anywhere in Portugal. Please note, we do NOT take ebikes on this tour.

Please see the bike hire page for more information on the various models available, our recommendations and pricing.

Riders are not obliged to hire through Cycling Rentals but if you use another company it is your responsibility to get bike(s) to/from the start/finish point etc.

Single rooms

For anyone not sharing, individual rooms can be booked but will involve an additional supplement of around €275. 

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.

Crossing the frontier near Segura

Supporting a worthy cause

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

What now?

Read what previous riders thought on our reviews page or keep scrolling down for more pictures from previous Eastern Frontier trips.

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 contact me via pedalportugal@gmail.com

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

For further tour news and other information on biking in Portugal don’t forget to also check out our Facebook page and blog