Portugal continues to place high on International Living’s Retirement Index year after year, with good reason. It’s challenging for other nations to compete with its combination of varied landscape, compact size, fresh foods, affordable healthcare, rich history, and the gracious nature of the locals.
So when, not if, you find your way here, what are the most important cities to see?
Almost half of the country’s population of approximately 10,404,000 is concentrated between two major metropolitan areas: the capital, Lisbon, and the “second city” of Porto, so these are essentials.
Additionally, from north to south, here are some important urban centers on the mainland, as well as the capitals of Madeira and the Azores archipelagos off the mainland in the Atlantic Ocean west of Lisbon. I could list two or three times the number of places I’ve noted below, but visiting these will surely give you a solid idea of all Portugal has to offer.
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Viana do Castelo District
Viana do Castelo
If you want to be fully immersed in Portuguese culture and close to Spain, Viana do Castelo is a good option. This port town in the extreme northwestern region of the country reveals archaeological evidence dating from the Mesolithic era. By the 16th century, Viana do Castelo’s port, once used by the Romans, had become an important entry point for Portuguese explorers and traders importing textiles, tile, and glass, and exporting wine, fruit, and salt. It has also been one of the country's most important ports for the cod fisheries.
Close to the Spanish border, the town offers access to two international airports within one hour: Vigo, Spain, and Francisco Sá Carneiro in Porto.
Compared with other areas of the country, Viana remains quite affordable. There are apartments in this area with great access to the town, beach, university, and the airport in Vigo, Spain. Known as the jewel of the Green Coast, Viana do Castelo boasts a charming medieval center, tree-lined boulevards, and narrow lanes with Manueline manors and rococo palaces. Its location by the Rio Lima estuary means that Viana do Castelo is close to some excellent beaches and is a good base for exploring the lower Lima Valley and Serra d’Arga mountain.
Porto District
Porto and Vila Nova de Gaia
Situated on the banks of the Douro River, Portugal’s second-largest city has Celtic roots. It dates from the 4th century B.C., when it was a Roman settlement called Portus Cale, a name which led to the country’s name. From early times, it played an important role in trade between Braga and Lisbon, but it truly began to flourish during the Age of the Discoveries. In fact, it was the birthplace of Prince Henry the Navigator, known as Infante Dom Henrique in the city.
The Douro Valley is magnificent wine-growing country. In the 18th century, the British were at war with the French and therefore short on wine. Portuguese vintners began adding brandy to their products, thus creating port, to ensure their wine would travel the distance to England. Across the Douro from Porto, in Vila Nova de Gaia, today you can visit the legendary port wine houses and enjoy the fruit of hundreds of years of craftsmanship. Be sure to walk across the Dom Luís I Bridge, designed by none other than Gustave Eiffel of tower fame. It connects Porto to Vila Nova de Gaia and the port wine caves.
Braga District
Guimarães
Situated southwest of Braga, this former Roman city was chosen by the first king of Portugal, Afonso Henriques, to be his administrative base in 1128. With its 10th-century castle built to defend against invaders and a charming medieval quarter, Guimarães attracts tourists from around the world. You’ll therefore find shop and restaurant owners who speak English, but it’s definitely a Portuguese city. It feels much more rural than it really is, even though it's less than 45 minutes from Porto and the international airport. There’s a small-town feel to a city that has so much to offer if you want to be in a less cosmopolitan area. It has everything you might want, though, with many restaurants, shopping locations, and outdoor activities.
Castelo Branco District
Covilhã
This is another university town, though with a more local flavor than Coimbra. It is situated on the eastern flank of the Serra da Estrella mountain range, offering fantastic views of the mountains to the west and the plains stretching toward Spain to the east. It is more removed from the airports and hustle and bustle of the tourist and expat areas on this list, but it makes up for that with its shopping, dining, teaching hospital, and proximity to nature. There is skiing, biking, hiking, rafting, and just about any other outdoor sport you could want. It is also still a bargain compared to most other areas of the country.
Coimbra District
Coimbra
The Mondego River runs through this bustling city in the Beira Litoral province in the center of the country. Once the capital of Portugal, the city’s dominating feature is unquestionably its historic university. Originally established in Lisbon in 1290, it eventually moved in 1537 to its present location, perched high above the city on the site of a former palace. The oldest university in Portugal, the University of Coimbra, is also one of the oldest universities in continuous operation in the world. The Joanine Library is a must-see, renowned for its beauty and collections.
The author has lived near Coimbra on two occasions and has enjoyed the international cultural diversity, driven by the university, as well as the local communities that remain steeped in Portuguese culture. It is a fantastic blend of old and new, of tradition and avant-garde.
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Évora District
Évora
This city is the capital of the Alentejo region, noted for broad plains and a hot-summer Mediterranean climate. It is bordered on the north by the Tejo River and on the south by the Algarve region. Évora lies 87 miles from Lisbon and 50 miles from Badajoz on the Spanish border. With a history dating back more than 5,000 years, the city is a member of the Most Ancient European Towns Network, along with nine other cities, including Cádiz in Spain and Cork in Ireland.
Ancient megaliths, a Roman temple, and a Gothic cathedral are just some of the evidence of Évora’s fascinating past. It is a city on the move, though, as it prepares for 2027, when it will be the European Capital of Culture, with many events throughout the year. It is improving its infrastructure to make it world-class and better handle the increased interest in the city.
Lisbon District
Lisbon
The capital of Portugal is one of the oldest cities in the world, predating other modern capitals in Western Europe by centuries. Pre-Celtic groups, Phoenicians, Greeks, Romans, Germans, and Moors came and went, building the city’s rich culture. Lisbon survived the devastating effects of the Great Lisbon Earthquake of 1755 with the impeccable planning and care of the Marquis de Pombal.
Today, the hilly city on the Tagus, or Tejo, River is a mecca for business and commerce, arts and entertainment, and a veritable gastronomic wonderland. The city has at least 10 official districts, each with its own flavor. It is truly an international city that has something for everyone. It is dedicated to developing its pedestrian areas by restricting auto access and encouraging the use of its extensive public transportation.
Cascais
Once known as “The Portuguese Riviera,” Cascais is a former fishing village (you might notice there are quite a few of these) that has retained its traditions. Fishermen still depart early each morning for the catch of the day, which local residents enjoy, lunching on the wharf over steaming kettles of seafood soup. The hilltop fortress, built to protect the area from Spanish invasion, later served as a royal residence and is now a pousada.
The town is a major draw for visitors from around the world, who come for lovely beaches, laid-back ambiance, and food and wine to suit every taste. Notably, it is one of the more expensive cities in Portugal due to its appeal to expats from wealthier countries. There are a few bargains to be had here, but the sophisticated vibe and ease of getting by in English might be worth it for some.
Faro District
Portimão
In truth, the beach resort is named Praia da Rocha, as Portimão itself is a residential city about two miles north of the beach. Numerous sandy coves line this coastline, but the heart of the action is in the restaurants, bars, and nightclubs that line the cliff-top promenade in Praia da Rocha. The marina at the east end of the beach is a great walking area with a view of the beach and the river. It is a more residential city than its cousin about an hour to the east, Albufeira.
Tavira
Tavira is ideal for travelers who want to avoid the frenetic bustle of the central Algarve, but it’s not necessarily an ideal expat location unless your Portuguese is well-developed and you prefer a quiet, low-key lifestyle. From here, you can take a ferry or drive to Spain’s southwestern, rugged Andalusian coast.
Much of the city has been rebuilt in recent years, with high-rises and the construction of a mall somewhat marred the town’s architectural attractiveness, but it has retained many lovely 18th-century buildings. It has a lot to offer, including golfing and no fewer than 37 churches. The azulejos in Igreja de Misericórdia are particularly notable.
Also of interest, in the center of town, officials are currently excavating Roman ruins dating to the time of Christ, when Tavira was a Roman seaport.
Tavira has its own railway station on the line from Vila Real de Santo António to Faro and Lagos. From the Faro station, you can travel to Lisbon and the rest of Portugal.
If you want to take a break from local Portuguese cuisine, go Italian at Aquasul on the river walk at Rua Doutor Augusto Silva Carvalho No. 11.
Madeira
Funchal
An ancient subtropical rain forest once covered most of the main island of Madeira. In fact, it’s the reason for its name: madeira means “wood” in Portuguese and is also the name of the classic wine of the region.
The capital, Funchal, is known for its harbor and is an ideal base for exploring the mountainous island, a hiker’s paradise with peaks over 6,100 feet. Volcanic activity thousands of years ago yielded a fertile, green landscape, which many consider an unspoiled Hawaii. London-based World Travel Awards named Madeira, for the fifth time in 2018, “Europe’s Leading Island Destination.” It is an easy, inexpensive, short flight from Lisbon, making it a major destination for travelers from the mainland.
The Azores
Ponta Delgada
Settled in 1444, Ponta Delgada on São Miguel Island is the capital of the Azores. Like Funchal, the city’s volcanic past is strikingly evident, as a tour of the Sete Cidades Massif with its caldera, crater lakes, pumice cones, and lava domes attests.
Human history tells a story here as well: in town, the iconic 18th-century three-arched city gates bear the royal and city coats of arms. Grottoes, botanical gardens, and pineapple plantations abound, and a city-based tour company offers dolphin swimming and whale-watching excursions.
It’s more distant from the mainland than Funchal, but easily accessible by air in a couple of hours. It has a slower pace and a more traditional Portuguese flavor, although, due to increased international popularity, English is now widely spoken in most tourist areas.
Final Thoughts
From the medieval charm of Viana do Castelo to the cosmopolitan energy of Lisbon and the volcanic landscapes of the islands, Portugal offers remarkable diversity within a relatively compact country. Whether you’re drawn to a historic university town, a coastal resort, a mountain retreat, or a vibrant capital city, there’s a setting here to match nearly every lifestyle preference.
The key is not deciding whether Portugal has something to offer—it does—but determining which corner of the country best aligns with your priorities. Spend time in a few of these cities, explore their neighborhoods, talk to locals and expats alike, and you’ll quickly discover which one feels less like a destination and more like home.
Get Your Free Portugal Report Today!
Get Your Free Portugal Report Today!
Discover why we love a slower pace of life in Portugal and info on other European countries in our daily postcard e-letter. Simply enter your email address below and we’ll send you a FREE REPORT – Explore the Old World in Laidback Portugal.
By submitting your email address, you will receive a free subscription to IL Postcards, Overseas Dream Home, The Untourist Daily and special offers from International Living and our affiliates. You can unsubscribe at any time, and we encourage you to read more about our Privacy Policy.