Border Castles

12-DAY TRIP/10 DAYS OF CYCLING – from €1,580

Ride across the rolling landscape of the northern Alentejo on a guided bicycling tour, visiting some of the region’s oldest towns…and at least a dozen ruined castles.

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Riding through the Alentejo in April – on the way to Alter do Chao

Starting in the ancient city of Évora with its UNESCO World Heritage architecture, we’ll guide you on a circuit that runs along the border with Spain and up into one of the quietest corners of Portugal before looping back south again.

Along the way, we’ll ride along the banks of the Guadiana river, explore sleepy villages, stop in historic towns and visit castles ranging from dramatic hilltop eyries to some of the largest and best-preserved 17th century fortifications in Europe.

“Everything was perfectly planned with great routes, delicious food and drink, awesome castles and sights everywhere! I would highly recommend this group and biking in Portugal to anyone.” Amy Hillenbrand, Colorado.Border Castles strip 01


Departure/finish dates for this tour are: 

  • Spring 2023: Sunday 16th to Thursday 27th April – €1,660 Sorry, tour full

Why this tour?

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Castle at Alandroal

The Alentejo offers some of the best terrain for touring cycling anywhere in Portugal. There are few big hills or steep inclines but a rolling landscape that stretches off to distant horizons.

This is one of the least-populated parts of Portugal but dotted with towns and villages with a rich past. From megaliths to Roman temples and medieval castles to renaissance mansions, there’s plenty of history to discover.

Palaces, convents and castles hint at the region’s former wealth, while a string of once-mighty fortresses guard its eastern border.

The lack of people means most roads are quiet and there are sufficient country lanes to avoid the traffic on any major routes.

Agriculture is still one of the few major industries and you will ride for hours across an open landscape dotted with cork oaks, olive plantations, the occasional vineyard, and vast swathes of pasture. Birdwatchers will also be able to keep their eyes peeled for a wealth of avian life – from eagles to bee-eaters and storks to hoopoes.

Ranging from around 45-70km (28-44 miles), the main riding days present no major challenges for anyone who is reasonably fit and used to cycling. 

Note: Riders must be reasonably fit and able to cycle 60-plus kms on consecutive days. 

This region sees some of the highest summer temperatures in Portugal and spring (late February-early May) and autumn/fall (late September-early November) tend to be the best times for biking.

Both spring and autumn can see some wet days (mainly heavy showers rather than days of rain) but dry weather is much more likely. Whichever time of year you pick, you can expect plenty of sunshine and average daytime temperatures in April of around 16-26°C (60-80°F) and in October 18-28°C (65-82°F). 

The Alentejo generally looks a lot lusher and greener in the spring, with carpets of wildflowers stretching across its meadows, whereas the autumn can be hotter and drier.

Please note: all pictures used on this page are from previous tours or are of roads/locations on the tour and taken on previous visits to the region.

Portugal guided cycle tours

“Super fun vacation, riding on good roads with almost no cars…so well taken care of by Huw & Carolyn the whole time.

“We thoroughly recommend this bike tour to anyone who likes to ride free of gear, through rolling countryside, interspersed with interesting stops along the way.” Bruce & Jennifer Wilson, California.

Where do we go?

The tour explores the north-east corner of the Alentejo, skirting the Spanish border and visiting more than a dozen castles along the way before turning south-west to see more of the interior of this spectacular region.

We will visit UNESCO-listed historic cities, near-deserted villages and charming old towns, bicycling across sun-baked countryside dotted with cork oaks and olive trees.

Although not car-free, around 90% 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) in order to cater for a range of abilities and levels of fitness.

Starting from Évora, one of Portugal’s oldest and most unspoilt cities, the planned itinerary* is as follows:

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  • Day One: arrive in Évora and meet your fellow riders
  • Day Two: ride to the picture-perfect village of Monsaraz with its 14th century hilltop castle, cycling nearly all the way on quiet rural roads. 65km
  • Day Three: ride to the marble town Vila Viçosa, a former royal wedding gift with its 16th century ducal palace and quiet old centre. 55km
  • Day Four: our route takes a back road towards the Guadiana river, where the ruined fortress at Juromenha looks out at Spain. From there it’s north-east to Elvas, home to one of Portugal’s biggest and most impressive military complexes – where we stay in a former 16th century convent that was also a military hospital in the Napoleonic era. 40km
  • Day Five: take a complete rest day in Elvas or enjoy a morning’s ride out into the countryside to the north and visit the wonderfully preserved Nossa Senhora de Graça fort in the afternoon
  • Day Six: head north-east across more rolling countryside visiting a couple of small towns before ending at a rural hotel close to the edge of the Serra de São Mamede natural park. 60km
  • Day Seven: we head into a remote corner of Portugal, skirting around the spectacular hilltop village of Marvão, to Castelo de Vide, a delightful old town with a maze of cobbled lanes in its famed Jewish quarter. 50km
  • Day Eight: cycle out from Castelo de Vide to a spectacular Neolithic site, or have a day out of the saddle and wander the town’s cobbled lanes and go up to its impressive castle. There are also options for longer walks, including up to Marvão.
  • Day Nine: we ride south-west across a gentler landscape towards the monastery at Flor da Rosa and the old farming town of Crato, visiting one of the area’s biggest Neolithic tombs, before reaching Alter do Chão (with another small castle) where we stay in another old convent. 61km
  • Day Ten: we zigzag our way south via minor roads and a couple of small towns towards a hotel on the edge of a typical village. 55km
  • Day Eleven: our route continues through more typical rolling Alentejo country as we continue back towards Évora, joining a converted railway line for the last section into the city. 62km
  • Day Twelve (Thursday): morning transfer by bus or train back to Lisbon airport

*Please note: the exact itinerary may change depending on accommodation availability and other similar factors.Border Castles strip 02

How much?

The tour costs €1,495 per rider for our 2021 departures. 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 to and from Lisbon on Days One and Twelve***
  • 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.

***Transfers: We will book train travel between Lisbon and Évora on Day One or 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.

Portugal guided bike tours

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 etc. – and lunch on days other than on main route
  • 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 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 €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’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 Border Castles 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

Otherwise, please read our full terms and conditions before completing the booking form. For further tour news and information on biking in Portugal take a look at our Facebook page and blog