Last week we completed our toughest guided tour so far – riding from Portugal’s highest city, Guarda, to the Vila Real de Santo António at the mouth of the Guadiana river.

The Eastern Explorer covered around 600km over nine days of riding but also involved more than 7,000m of climbing. Along the way we crossed three regions of Portugal and one in Spain.
It would have been a fairly tough trip whatever the weather but the riding was made grueling by the fact temperatures were way above the seasonal norm – most days it got to 30°C (86°F) before lunchtime and then kept going.
Our tour group met in Guarda in the Beira region on Sunday 18th September, with nine riders along with myself and Carolyn as guides. Everyone was English-speaking (of sorts!) – we had four Australians, two Californians, two South African and one Hong Kong resident Kiwi.
We tried to start the trip off reasonably gently (which can be quite hard in Portugal, particularly if you want to see the really scenic spots). Guarda is perched on top of a big hill so it was mostly downhill to begin with as we skirted the edge of the Serra da Estrela before turning east to our first real climb on the way up to the fairytale castle of Sortelha, and then on to our first night’s stop at Sabugal.

Next came Monsanto. Another one of those places that’s very rewarding to stay in as you sit and admire the views. It’s just the getting up there that’s a real so-and-so!
Still, watching the sun rise from the ruins of the castle at the top of the hill was something special. And walking around the place feels a bit like you’ve strolled into a film set – all those higgledy-piggeldy paths, house nestled among giant granite boulders, and very few signs of the modern world.
After two nights in Monsanto – wonderfully looked after by the ladies of Casa Pires Mateus, who couldn’t speak a word of English but were sure Google Translate would answer all problems – we took a detour into Spain.

For our night in Spain we stayed in the old town of Alcántara. Not a hilltop village this time but there was a steady climb up to our accommodation in an old convent after crossing the Tejo via an old Roman bridge. Not quite the original as it’s apparently been blown up a couple of times but still impressive.
The rolling landscape of Extremadura was fast riding – we didn’t want to hang around too long after spotting the vultures watching us and circling overhead.

After sneaking back over the border into Portugal via a tiny road we came to our next stunning destination of Marvão – and yet another slog uphill in the afternoon heat to get to the walled village and it’s gorgeous hills. By this stage I think the group were beginning to understand what I meant by a ‘significant’ climb.
One of our riders, Simon, had a spoke break with only a few km to go that day but we were all highly impressed by the service provided by hire firm Cycling Rentals. A taxi came and took the wheel away to a bike mechanic in Portalegre (about 30 mins away) and it was returned to us not much more than two hours later as we were enjoying our evening meal.
Now in the Alentejo, the next day began with some rugged country as we took some back roads through the Serra de São Mamede, then it was down to much more rolling terrain as we headed south-west to our next night in a converted farm near the village of Terrugem.

After a couple of 80km days, we took a slightly shorter route to Monsaraz. A gem of a place. Known locally as ‘The Eagle’s Nest’, which might give an idea of the ride involved in getting up there. Monsaraz is one of my favourite places in Portugal. It can be a bit touristy and gets overrun at times by day but it’s a magical place to stay the night when the majority of visitors have disappeared and you can look out for miles in all directions.
We stayed two nights in Monsaraz – for some reason none of our riders were bothered about getting on their bikes on our second ‘rest’ day and were happy to spend the day mooching around the village (mostly avoiding going out into the sun as it was stinking hot at this stage).
After that, the group (well, most of them anyway) were raring to be off at the crack of dawn. Not sure if it was because they were enjoying the cycling or because I’d told them the forecast was for the temperature to hit 34°C (93°F) in the afternoon.

The rolling roads continued south around the huge Alqueva reservoir and up to Moura, where many of us fell in love with the charming Hotel de Moura.
Next day we cracked on through more wild back country – and our longest day’s ride of 84km – to the ancient river port of Mértola, perched above the Guadiana river.
The last day took us on a fairly up-and-down route as we left the Alentejo and crossed over into the Algarve. There was one gentle section (interrupted by a fairly minor hill) as we followed the banks of the Guadiana south from Alcoutim… and then the inevitable ‘significant’ climb to get out of the valley for the last rollercoaster section before dropping down to our final destination of Vila Real de Santo António – the most eastern town of the Algarve, set at the mouth of the Guadiana and just a stone’s throw from the Gulf of Cadiz.
I had been wanting to ride this route for ages and it was a superb trip, although fairly demanding. Huge thanks to our riders, Mel & Mark, Simon & Sue, Chris & Sue, Gayble and Maureen & Paul for signing up and making it possible. Hats off to you all for making the journey. Hope you enjoyed it as much as we did!
For more information on this route and other tours planned for 2017, please see the Guided Tours page.
