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Lost in Lisbon Part 3: A Day Trip to Alentejo!

Most folks who visit Portugal discover the country only after completing the boilerplate Euro trip to France or Italy. Certainly, this was my experience. Even those pining for Southern Europe more often venture to nearby Spain. Barcelona, Madrid, San Sebastian, and Valencia are magnificent cities and worthy spots, but they are also well known to the tourist zeitgeist. There is something virginal about multi-faceted Portugal; it possesses a rare, almost quixotic mystique of wild variations worlds beyond Porto and Lisbon. Forget the big cities, trolly rides, and tourist traps and gas up for medieval times done properly with Portuguese flare. I give you Alentejo!

I decided to take a day trip to Alentejo (“alem”+“tejo” = Beyond-the-Tagus) after coming across a Janz Anton-Iago’s YouTube video on the “Underrated Parts of Portugal” (I promise you will find the visuals as splendiferous as I did). Alentejo is a region south of Lisbon that spans three provinces (Alentejo, Ribatejo, Estremadura) all the way to the stunning beaches of the Algarve. What strikes you almost immediately after crossing the Ponte 25 Bridge over the Tagus River is the landscape. Plenty of countries from New Zealand to the United States render landscapes so colossally distinct from region to region it feels like you are jumping continents. Portugal has the same effect, an impressive feat for such a small country.

Words unfailingly fall short of reproducing the emotional effect of retina-infused stimulus on the soul (so do YouTube videos). It reminds me of Renoir’s homage to Rembrandt: “I sniff the gravy, he chews the meat.” Renoir was a great painter in his own right so let fly my humble verbal droplets of decorative descriptive; just know that there is no facsimile for lived experience. Alentejo is coated in rolling valleys of pastel-green plains, lush sobreiro (Quercus subers) trees that appear as if air-lifted from the African plains and perfectly placed for ocular delight. The towns glitter in glazed ice-cream white paint accented with golden yellow – sometimes crayon blue – doors and shutters often conjoined under rustic burgundy roofs.

Perched atop the hillsides overlooking ancient towns and mythical valleys are crenellated castles just as Don Quixote and Sancho Panza might have seen them.

Perched atop the hillsides overlooking ancient towns and mythical valleys are crenellated castles just as Don Quixote and Sancho Panza might have seen them. The two medieval outposts I sought were Evora and Estremoz. In truth, you could spend a lifetime hopping from one Portuguese town to another in an unending fairytale of feudal splendor transported from the Age of Chivalry. Or you could simply pull the car off the road and sprint in any direction: east, west, north, or south. Either way, the compass magnet will point you toward true bliss.


Estremoz is not as large as Evora nor is its castle as imposing, but the panoramic vista of the valley below might be the most incredible landscape these eyes have ever seen. The best approximation I can give you is the short video below. Wow! Stroll through the town, eat some delicious lunch, replenish your Vitamin C with citrus from the orange trees that line the streets, and absorb the charitable warmth of the locals, human beacons transmitting the solar power of rapturous sunlight. Does life get any better than this? I am not so sure.


My final stop was Evora, less bucolic, more city than town, though no less beautiful. The churches, side-streets, hotels, and Roman ruins make Evora another must see. It is a smidgeon more touristy than other options like Sines or Elvas, which means plenty of eateries, restaurants, and scattered local nightlife. The best thing to do is find a well-situated bench across from the Roman ruins and stare into paradise. Perhaps it will give you pause – as it did me – to contemplate the natural beauty, architectural arete, the timelessness of life, and your place in it.

Seeing Evora and Estremoz brought me closer to Miguel de Cervantes. In the modern age of YouTube shorts, 10-step programs, Tik Tok videos, fat-pills, and get-rich-quick scams one thing seems abundantly clear – the demand for a renewed idealism is rising if it ever died. Is this thirst for inspiration what Cervantes tapped into when he wrote parodies of a delusional knight and his enabling squire stumbling through a neo-world that no longer cared for antiquated notions of service, honor, and knighthood? Maybe his message was less a mockery of sunsetting traditions than a warning. Through Don Quixote, Cervantes was communicating that modernity is a fluid concept that challenges every generation, but service and romanticism are enduring features of the human psyche that makes life for the adventurous well worth “tilting at wind mills.”

A day trip to Alentejo will make you a believer. More revelations to follow after my next trip to Portugal.

Té logo!


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