Europe,  Travel

Alentejo Region of So. Portugal June 7th – 9th

June 7th – After meeting our Backroads Group in Lisbon, we head southeast to the Alentejo Region through “New Lisbon”, over the second longest bridge in Europe to the other side of the River Tagus (Rio Tejo), and on through rural Portugal and to the ancient town of Monsaraz, one of the country’s oldest settlements in the heart of southern Portugal. Here we’re introduced to the region’s hearty fare with lunch at a historic olive oil factory and charming local restaurant.

Alentejo Region was the 2nd part of our trip to Southern Portugal. Algarve Coast would be the last.
First Afternoon in Alentejo Region and walking to lunch spot
My bike leaning against a cork tree that was last harvested in 2017
Overlooking Alqueva Lake into nearby Spain
Hilltop town of Monsaraz in background


After lunch, we cycled 22 miles through the rolling hills past vineyards, olive groves and cork fields with a climb up to the medieval town of Monsaraz for views over Alqueva Lake and into Spain. We finish our ride with a descent to São Lourenço do Barrocal, an amazing hotel housed in a former agrarian estate and our home for the next two nights. After a beautiful Welcome Reception on the grounds of the hotel, we ended our first day with dinner at the hotel’s restaurant, while being serenaded a cappella by a local group that sing traditional Portuguese songs. 

Our local singers serenading us at our dinner spot at hotel

June 8th – After cycling 30 miles in the morning, we stop and have lunch in the medieval hamlet of Alandroal at a rural guesthouse with a lecture on the local cork industry.  Portugal produces roughly 55% of the world’s cork and it takes 9 years for cork to regrow on a cork tree before it can be harvested again.

Biking through cork tree forests
A Cork Tree that was recently harvested in 2021

We biked 30 miles in the morning and stopped halfway for some coffee in a beautiful village.

Our coffee stop with our bikes parked.
e-bikers lead way out of town – riding over cobblestones in all of these small towns was not fun!

Our lunch spot was beautiful with a pool overlooking an old Olive Orchard. Some of us put on our bathing suits and took the opportunity to cool off in the frigid water. After lunch, I cycled another 12 miles through beautiful rolling terrain before stopping to catch the van shuttle back to the hotel and some time by the pool.

My lunch near the pool overlooking a beautiful olive tree grove

Later, we took an early evening walk through the narrow streets of Monsaraz lined with whitewashed houses. We also walked through the magnificent castle at the town’s edge, part of which is still an operating bull ring. And Monsaraz is one of the few towns or cities in Portugal where killing the bull is allowed.  Perched high atop the hill, the castle had magnificent views of the surrounding countryside and the Alqueva Lake all the way across to the Spanish border.

Walking through Monsaraz

We had dinner in this quaint hilltop town at Isabel’s. Our amazing dinner included fresh salads, local cheeses, cured meats, Fava Beans mixed with acorn fed pork, cod casserole, and black pig cheeks. Not only was the food unique and delicious, but fellowship may have been even better. We ended up doing shots of some local brandy, including Isabel’s own concoction, which she shared with us. In the spirit of the moment, I bought a bottle. After dinner we shuttled back to our hotel.

Dinner at Isabel’s
Isabel herself – she did several shots with us after dinner!

June 9th – Today we cycled through the Alentego Region into Évora, the historic capital of the Alentejo region.  Like all Backroads Trips, we sit with different people at various meals, which means that we get to know everyone and their stories. This morning, I had breakfast with the four guests from the San Francisco area, where I learned of the significant outcome to recall the current District Attorney, who was seen as being too soft on crime.

Our breakfast spread

The reason I mention the San Francisco recall is because you always learn something interesting from your fellow travelers.  And my San Francisco traveling companions were very animated about this local topic. They believe that this could become a hot button in future elections in other parts of the country. They point to Portland, Oregon as an example of being too soft on crime. And we all agreed at our table that Portland has become a ruined city because the city lost control, which brought in more troublemakers and anarchists. And I did see the result of this firsthand when I visited Portland last year.

Church at our mid-morning coffee stop

Now, back to our trip! Shortly into our ride, we stopped for a brief pottery demonstration, where I bought some beautiful pottery presents for family and friends. Passing through quiet villages, vineyards, and silvery-green olive trees, we stopped briefly after 12 miles in a village for coffee, and then pedaled another 10 miles to our lunch spot, Herdade da Furada, an operating farmhouse, to enjoy a picnic lunch by the pool followed by an olive-oil tasting. Again, several of us took a dip in the cold water.  I needed it after my morning ride.

A view early into the second half of our morning ride

The following explains why I was so hot after our morning ride. This is the first Backroads cycling trip where more people are using e-bikes (8 out of 13) instead of regular bikes. The previous high may have been 25%. This is huge in that it totally changes the dynamics of the riding day. Instead of being one of the first riders to finish each day, I am one of the last.

Goat cheese and olive oil tasting at lunch

However, I decided on this last 10-mile leg before lunch that I was going to try to finish this stretch with the lead e-bike leaders. However, with a headwind I needed help. Bill, a 35-year-old from Dallas, Texas, and a former triathlete, came to the rescue. I say former because as the dad of two young children, he no longer competes. He let me draft off him for the first 5 miles. Drafting is a technique used in team bike racing where the person in front takes all the headwind and allows the person behind him to draft, thereby allowing the second biker to use much less energy. In fact, if done properly, you almost get sucked into the vacuum the lead bike creates.  As a result, I was able to almost sprint the last 5 miles while strategically attacking the gentle hills. And thanks to Bill, I was able to finish with the e-bike leaders. I think they were very surprised when I caught them just as they were turning into the driveway of our lunch spot!

It will most likely be the only time that I finish with the e-bikers because when we get to the Algarve region, there will be many more hills. And steeper hills. And that is where the e-bikers really kick your butt. But I will always remember that 10-mile stretch where strategy and hard work came together to allow me to finish with the leaders. And although it was a lot of fun, I was spent!

Our olive oil expert with a part of our group


After lunch, I skipped the afternoon ride, partly because I had ridden so hard in the morning, and hopped in the shuttle to visit historic Évora, the region’s capital city. Designated as a World Heritage site, this spectacular town is surrounded by medieval stone walls and is a member of the Most Ancient European Towns Network. A vibrant university town today, Évora’s rich and diverse history is visible in its architecture, influenced by Roman and Moorish cultures.

Our hotel, the Convento do Espinheiro Hotel & Spa, a converted 15th-century palatial convent, was situated just outside of the historic center of Évora. Like Avignon in Provence, Verona in Northeastern Italy, and Chefchaouen in Northern Morocco – Evora is a perfect gateway city to exploring the Alentejo Region. I would highly recommend visiting this region and this city. And if you do, stay at Convento do Espinheiro Hotel & Spa! It is an easy ride into town, but you feel like you are in a wonderfully isolated oasis. The property is spectacular with several restaurants, gardens, pickle ball, tennis, and even a dog park for those who bring their dogs! Due to its well-preserved old town centre, still partially enclosed by medieval walls, and many monuments dating from various historical periods, including a Roman Temple, Évora is a great walking town.  However, due to its inland position, Évora is one of Portugal’s hottest cities in the summer, frequently subject to heat waves, which is another reason I skipped the afternoon ride. It reached over 100 degrees today. This was by far the hottest day of our trip.

Roman Ruins in Evora


A brief history. Because Evora was at the crossroads of several trading routes, it was an important city for thousands of years. Conquered by the Romans in the first century, it was also an important City in the Roman Empire. The Romans lost control of the city to the Visigoths in the 5th century. In 715 the city was conquered by the Moors. During the Moorish rule (715–1165), the town began to prosper again and developed into an agricultural center with a fortress and a mosque. The Moorish influence can still be observed in the character of the historical city. 

Évora was wrested from the Moors and came under the rule of the Portuguese king Afonso I in 1166. It then flourished as one of the most dynamic cities in the Kingdom of Portugal during the Middle Ages, especially in the 15th and 16th centuries, when Portugal was a global economic powerhouse. The court of the first and second dynasties resided here for long periods, constructing palaces, monuments, and religious buildings. Évora became the scene for many royal weddings and a site where many important decisions were made, especially for a Portuguese Empire that controlled most of the overseas trade routes, until other European countries, including Spain, England, and France, began to erode Portugal’s dominance.

Our beautiful hotel – a converted 15th-century palatial convent

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