Guadiana River Guided Tour 13th to 17th January 2021

Activity: Guided Touring Bike holiday
Date: 13th to 17th January 2021
Bike type: Touring Bike (optional e-bike/MTB)
Duration: 4 nights 4 days cycling
Activity Level: Intermediate
Accommodation: Quality rural hotel and B&B
Daily Average: 60km
Price: €525

This four day guided tour takes in the natural beauty of the Guadiana and its surrounding towns and villages. Every day brings with it a new experience as we follow the twists and turns of the river, cycling on quiet, empty roads and enjoying the unassuming authenticity of the region, far away from the tourist resorts that characterise much of the Algarve coastline.

You could be fooled into thinking that cycling along the riverbank is fairly flat. However, we will leave the valley for higher ground in places. This makes for an even more interesting ride, of course, and the ascents soon give way to spectacular views of the bending and twisting river and the far-reaching countryside beyond.

We have designed this trip for those who cycle regularly and appreciate the odd challenge, but who enjoy a relaxing pace and are interested in the nature and culture that surrounds you as you navigate through ever-changing landscapes.


Guadiana River Guided Tour 9th to 12th January 2020

Day 1 Vila Real de Santo António – Alcoutim: (47km, 600m elevation gain)

We will meet in central Loulé, where we will be transported with our bikes and luggage to the beginning of the route and to our first sight of the majestic Guadiana River, at Vila Real de Santo António. After a quick coffee and briefing from our tour leader, we will set off towards the ancient settlement of Castro Marim. We will initially enjoy views across the widest point of the river to Spain, before turning off to traverse the salt pans (a still thriving local industry), and entering the town via the medieval castle.

Heading out through the nature reserve we are surrounded by marshlands, where we may spot some interesting wildlife, before continuing North and leaving the last remnants of the Algarve tourist region behind us.

Here the landscape starts to change and we will climb a little as we follow the road that runs parallel to the river. It is an opportunity to really savour the peace and quiet of this region, as we pedal along country roads, punctuated by small villages filled with tradition. We can stop and sample the homemade sweet pastries and admire the locally mined slate houses (known as xisto) that are populated by generations of families who still live life according to the old customs and beliefs. It seems like the more we pedal forward the further back in time we go!

Eventually our route takes us close enough to the river that we can actually dip our toes in. There’s a museum and a roman excavation along the way or we may just fancy a cold drink and a peaceful break at one of a number of cafes that we will pass.

After a final climb we descend into Alcoutim, our destination for tonight. It is a beautiful town with a rich history and an impressive castle that overlooks the river, surrounded by typical white houses on narrow streets that reflect the traditional way of life. Dinner will be a local affair with the opportunity to sample fresh fish from the river or the home reared smoked ham and sausages.

Day 2 Alcoutim – Mértola: (48km, 790m elevation gain)

Our second day’s cycling is a complete contrast to Day One as we make our way through the interior Algarve and enter the Alentejo, the land of wheat and bread produce. It’s a vast, scarcely populated landscape with a noticeable lack of establishments serving food and drinks, so it’s a good idea to go prepared with plenty of water and snacks, which we can stock up on before we leave Alcoutim.

Leaving the hotel this morning the biggest climb of the day greets us almost immediately! But we are in no rush, so we can wind our way slowly up and out of town as we look forward to another day of new experiences.

As we head inland the roads become straighter and we begin to appreciate the vastness of this land as we cycle along narrow lanes surrounded by low-lying hills. Punctuated rarely with the odd farmstead we go for long stretches where the only sign of human life is the manmade dry stone wall that lines the road. Eventually we reach Giões, probably the largest village we will encounter before our day’s destination, so we will stop here for a break and a bite to eat. Suitably refreshed, we will continue towards Mertola, crossing the Vascão river, which forms the natural border between the Algarve and the Alentejo.

Dating back to Roman times, Mertola is beautifully located on the crest of a hill and makes for a dramatic scene as we approach it, with its castle and city walls that dominate the landscape. It is known as a museum city because it has so many ancient buildings and places of interest intact, so it is worth a slow exploration on foot.

Day 3 Mértola – Serpa: (65km, 947m elevation gain)

The central theme for today’s ride is the Vale do Guadiana Natural Park, a huge area of open country where farmers and wild animals live in relative harmony. This is the land of wild boar, vultures and the endangered Iberian lynx. So you will want to keep your eyes open for some rather special photo opportunities. The ride is slightly longer than most days and fairly tough in places, but worth it for some of the spectacular sites you will see.

Leaving Mertola across the river we will head East through the park towards Mina de São Domingos, passing through a couple of small villages along the way. There is a beautiful Praia Fluvial (river beach) just outside of town, so this could be an interesting spot to linger in for a short time and catch our breath.

From here the road is long and straight, so it’s a good opportunity to pick up the pace and put some kms behind us (but keep half an eye out for those lynx!). Before too long we will arrive in Vale do Poço, a pretty little village, where we might like a quick break before the final leg.

With about 20kms to go, we will have an opportunity to take a small diversion of around 4kms to see the famous Pulo do Lobo (wolf’s leap). This is a very pretty spot on the Guadiana river, where a waterfall has carved out a gorge and, according to legend, is narrow enough for a wolf to cross it in a single leap. We will cross the river ourselves (though on two wheels) before the final climb of the day.

We should reach Serpa in time for a walk around. It’s a charming working town that produces all manner of goat and sheep related products. As we stroll past the impressive gates and walls of the medieval castle, be sure to notice the natural stone pavements of which they are so proud that they hold an annual competition to see which are the whitest!

Day 4 Serpa– Monsaraz: (79 km, 949m elevation gain)

Today’s route from Serpa to Monsaraz takes us right through the heart of the Baixo Alentejo (Lower Alentejo). This is a region of undulating hills, extensive olive groves and waves of vineyards that produce some excellent wines (we will certainly have earned a glass or two at the end of this, our final day!)

Travelling through sleepy villages we will begin to appreciate the different pace of life here. It’s not uncommon to see people sitting around in the village square or in front of the church, just chatting or dozing in the shade. They will no doubt sit up when they see strangers on bikes passing by…but a smile and a wave is all that’s required.

A natural place to stop for refreshments is Moura, with its narrow cobbled lanes and low whitewashed cottages. Its Moorish quarter is one of the best-preserved in southern Portugal.

From here we will continue North, skirting the Aquelva Reservoir. Reportedly the largest man-made lake in Europe, it certainly makes its mark on the Alentejo landscape. Stretching as far as you can see it is a serene stretch of water that is framed by natural beauty and punctuated with the odd cow or sheep herd on its shores.

As we navigate our way around the lake we will pass through Póvoa de São Miguel. This is an unassuming little place, but significant because it provides us with our first glimpse of Monsaraz Castle, way up on a hill in the distance. This is where we are headed for the night.

From here we will pass just one more town, Mourão, before we cross the lake and tackle our biggest climb of the day, up to the fortified town of Monsaraz. But it is well worth the effort. With fantastic views over the Alentejo plains and beyond, it is a well-preserved old town with plenty to explore as we stretch our legs after the day’s riding, including excellent restaurants serving honest, local food. This is a perfect place to end our trip on a real high!

Day 5 Departure

We will transfer you from your accommodation for your journey home.




Price per person, based upon two people sharing a twin/double bedded room, is €525pp

Single room accommodation subject to availability, please specify if preferred .


  • Transfer between the Central Algarve and Vila Real de Santo António on Day 1
  • Transfer back to the Central Algarve from  Monsaraz on Day 4
  • 4 nights b&b stay in comfortable guesthouse or hotel based on 2 persons sharing a twin room.
  • Daily luggage transfer between accommodation


  • Flights to and from the Algarve
  • Lunches and evening meals
  • Bike rental is available on request
  • Helmets and SPD pedals. You can hire at a small fee, but we suggest you bring your own
  • Personal accident insurance, which we strongly recommend you take out.