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Yes, Portugal is on the demand for a while, and it will stay for a long time on the scope of travelers who seek a destination to enjoy their retirement.

Nevertheless, if you’re a first-timer in one of the oldest countries in Europe, there are a few places in Portugal that you should not miss, worth spending a couple of days.


#1 Évora

The capital of the southern region of Alentejo, Évora will be considered the European Capital of Culture in 2027.

Just a short road trip from Lisbon, Évora encompasses a small unscathed town in history and time, presenting us with a small Middle-Ages town in Portugal. With its foundations settled in prehistoric times, when hunters and gatherers established in this territory, Évora experienced its urban planning and evolution during Roman times. Julius Cesar named Ebora Liberitas Julia, in order to claim this town within the concept of Romanization and a small part of the Iberian Peninsula to be included within the Roman Empire. Even in the 21st century, you can still encounter a few traces dating back to the Roman Empire in this town, such as the Roman Baths and the iconic Roman Temple dedicated to the goddess Diane.

Only in the 15th century, the Portuguese monarchy decided to settle an imperial residence, a palace to spend their holidays in the south, making Évora quite important beacon during the Renaissance times.

As we progress to the 19th century, Évora, alongside Lisbon, Porto, Guimarães, Braga, Cascais, and other important cultural hubs in Portugal, witnessed a great urban phenomenon and demographic growth, tearing down the old Middle-Ages concept, while still preserving a bit of its own charm and beauty from the Dark Ages. Nowadays, walking in Évora feels like enjoying a breathtaking film, where it’s almost always sunny, and street vendors, local restaurants and artists can be found at the heart of the city – The Giraldo Square.

Giraldo Square

Lose yourself in the old and narrow alleys from the past, where the old walls of the city are still there to be seen and photographed. Heading north, you will see a huge aqueduct, built by Francisco Arruda, which is a marvel of the 16th century in Portugal, a few of which are left intact and well preserved. After a morning walking tour around the old town, it is time to quench your thirst with local red southern wines from Alentejo, paired with goat and sheep cheese and pork ham from the region.

The afternoon could be well spent by visiting an interesting site – a chapel full of old bones from the 17th century. Elected as National Monument in 1910, the Chapel of Bones belongs to the Franciscan order, this religious structure was built to avoid the construction of many religious sites that were already planned or built in Évora, and the Franciscan order removed all the bones from these sites, in order to allow the city to grow exponentially. This Baroque monument is definitely worth a visit while spending a couple of days in Évora.

Roman Temple


#2 Cascais

Cascais, nicknamed recently as Portuguese California, is a 2023 travel destination if you plan your holidays in Portugal.

In the past 3 years, the American Dream has set goals in the Portuguese coastline, especially Cascais, the ivy-league town for foreign investors, digital nomads, and seaside activities. Portugal and Spain`s post-pandemic had a significant tourism and travel increase from the USA, Canada, Australia, and South Africa, where a few are looking for a place to retire and spend their days enjoying the sunny days in small towns such as Cascais.

Cascais Beach

From the Neolithic era, like Évora, Cascais had a Roman settlement where a number of villas were built along the shoreline for vacations, as well as exploring ocean resources. If you’re an art lover, while navigating through the old town, you will see architectural remnants from the old Islamic Empire, especially small and colorful Arabic ancient houses from the Middle Ages.

During the Golden Age of the Portuguese Discoveries, fishing was still the main industry of Cascais. Yet, the town started to appear in a few medieval maps and cartography like the Civitates Orbis Terrarum from the 16th century, spiking the curiosity of navigators and merchants.

Cascais Farol

The second half of the 1800s was an important turning point for Cascais. After the French Invasions (1807-1810) that left mayhem in Portugal, the town started to be sought for the ocean and sunbathing. The wealthy merchants and bourgeoisie, during the weekends, cultivated the tradition of going to the beaches of Cascais for relaxing. It increased a lot more after the renovation of the old road to Oeiras between 1859 and 1864. By the late decades of the century, Cascais was already the top-notch town for the Portuguese and British elite. Even princes and princesses enjoyed a really good time in the town of Cascais.

It is mandatory to try the traditional fish out of the ocean, which is the seam brim, sea bass, sardines, and the exquisite octopus with rice. After a delicious lunch, why not venture to the famous geographical landscape called Boca do Inferno (Hell’s Mouth) and admire the astonishing ocean views. The name Boca do Inferno comes from the horrendous geological condition of the land and the waves crashing into them, where the sounds resemble something eerie and from another world. Many travel bloggers and wanderers seek the perfect time for the perfect picture to be taken during sunrise or sunset hours.


 #3 Porto

The “capital” of the north of Portugal, during the last decade Porto has won a few cultural and tourism awards, bolstering the city yearly to be sought by many visitants and travelers.

The city has been experiencing an urban renaissance, particularly with the development of the new subway line that within two years will connect the Santo António Hospital (nearby the Tower of the Clergy) to the Boavista quarter.

Tower of Clergy

Nowadays, if you venture through the old alleys of Porto’s old town, you will find miscellanea of both tourists and residents, as well as many opportunities to live and invest. Several areas are becoming quite popular after renovation and refurbishment. The parish of Cedofeita, well known for being the artistic district, is witnessing not only the growth of Airbnb’s but also co-working places for digital nomads or US expats. Not far from the city center, and part of Cedofeita, you also have the Boavista quarter, a 19th-century-old area, crawled with coffee roasters, IT and marketing offices, high-end hotels, and music venues.

For a first-timer, it is highly recommended to exit in Trindade metro station and head towards the financial district of Aliados. At the bottom, be amazed by a hidden gem, considered to be the most beautiful McDonald’s in the world, winning already an architecture prize. Embellished with Art Deco stained glass and chandeliers that will take you back to the Roaring ’20s, the McDonald’s of Aliados is a must for photography lovers. Afterward, it’s time to head to the bookstore that influenced a whole wizard saga – Lello & Irmão Bookstore. Be aware if you want to skip the line to visit this Harry Potter bookstore, try to purchase the fast-track tickets online at their website. Not far, on the way to the previous Jewish quarter, lies what used to be a beacon of light in the 18th century, the Tower of the Clergy. Climbing the 240 steps, all the way to the top, you have a 360º view all over the city. Don’t skip the church too, where you can admire Baroque art and the history of an Italian architect who shaped the city’s artistic view with religious buildings and villas.

Porto Old Town

Save your lunch in one of the traditional and outdoor restaurants nearby the Square of Lisbon, where the olive trees decorate the landscape. Local dishes can be tasted such as the unforgettable Portuguese croque-monsieur Francesinha, combining a variety of meats; the Codfish Brás with olive oil and olives; the grilled sardines especially during summertime or go for something more traditional and try out the most ancient dish nicknamed the locals – Pork Tripes.

Escape from the hustle and bustle downtown area by hopping on the old tram nº 1 heading to the seaside area of Foz. Be delighted with the ocean vistas, vintage cafes, and outdoor activities, following the sea breeze. What once was a 19th-century elite aristocratic area for going to the beach on the weekends today is an often frequented neighborhood by everyone who seeks to enjoy a good wine or coffee under the sun. With the tourism growth, Foz is turning into a procured high-end location for foreigners who, like Cascais, are investing from small properties to big villas facing the ocean, similar to Monterey, Los Angeles, or even San Francisco. It is not a new phenomenon that Portuguese coastal towns are seldom coveted by expats or digital nomads. After all, who wouldn’t enjoy living just a few seconds from the ocean?


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