Lisbon is the oldest capital in Western Europe — founded by Phoenician traders around 1200 BCE, settled by Romans, Visigoths and Moors, reconquered by Afonso Henriques in 1147, and rebuilt after the earthquake and tsunami of 1755 destroyed 85% of the city in six minutes. The rebuilt Lisbon — the Baixa Pombalina, the grid of seismic-proof streets laid out by the Marquis of Pombal, the most complete example of 18th-century urban planning in the world — coexists with the surviving medieval neighbourhoods of Alfama and Mouraria, the Moorish quarters that survived 1755 because their irregular geometry absorbed the shock that destroyed the rational city below. This juxtaposition of the planned Enlightenment city and the organic medieval neighbourhoods gives Lisbon its specific character: a city that is simultaneously logical and labyrinthine, modern and ancient, simultaneously European and Atlantic.

The Mosteiro dos Jerónimos (Jerónimos Monastery, begun 1501, Manueline style — the specific Portuguese Late Gothic that incorporates maritime imagery, armillary spheres and exotic decorative elements from the discoveries) is the greatest building in Portugal: the main portal by João de Castilho is a tower of carved stone 20 metres high, its columns writhing with seaweed, coral and rope. Vasco da Gama is buried in the south nave. The cloister — 55 metres per side, two storeys, every column and arch different — is the finest piece of Manueline stone carving in existence. The Torre de Belém (1516, also Manueline) stands in the Tagus 200 metres from shore where the river narrows before the sea begins — the exact point where every Portuguese expedition departed for Africa, Brazil, India and the Spice Islands.

Fado — the specifically Lisbon music of longing, loss and the untranslatable concept of saudade (a melancholy yearning for something absent, beautiful precisely because it is gone) — is performed in the casas de fado of Alfama and Mouraria, the two surviving Moorish quarters. The best fado performances happen late (shows start at 9pm, peak at midnight), in small rooms where a single fadista in black sings accompanied by a Portuguese guitar (12-string, with a distinctive metallic resonance) and a viola baixo, and the specific intimacy of the form — the singer's physical relationship with the melody, the audience's silence, the glass of Alentejo red — is unlike any other musical experience in Europe.

Porto is the city that made Portugal rich — specifically, through the port wine trade that developed in the 17th century when British merchants discovered that fortifying wine with grape brandy (to survive the sea voyage) produced a wine of extraordinary quality and durability. The Port wine lodges of Vila Nova de Gaia — the south bank of the Douro, directly opposite the city — contain over 300,000 casks of ageing port wine from houses established in the 1700s: Taylor's, Graham's, Sandeman's, Quinta do Crasto, Niepoort. The lodges are open for tastings, and the walk along the Gaia waterfront at sunset, tasting a 20-year-old Tawny port in the shadow of the barrels where it was aged, is the most specifically Portuguese experience available in any city.

The historic centre of Porto — the Ribeira quarter on the Douro waterfront, the Bairro da Sé around the cathedral, the Baroque churches of the upper city — is a UNESCO World Heritage site of extraordinary density. The Igreja de São Francisco (1410–1425, Gothic exterior, interior encrusted in the 1690s with approximately 100 kilograms of gold leaf applied in Baroque exuberance that is the most overwhelming interior in Portugal) is the single most unexpected building in the city: nothing in the sober granite exterior prepares you for the golden frenzy inside. The Estação de São Bento (1916) is a railway station whose entrance hall is lined floor-to-ceiling in 20,000 azulejo tiles illustrating the history of Portuguese transport and conquest — the finest public tile programme in the world and one of the most extraordinary spaces in any European railway station.

Livraria Lello (1906, Neogothic, the 22 steps of its red helical staircase frequently cited as an inspiration for J.K. Rowling's moving staircases at Hogwarts) is the most beautiful bookshop in the world and requires advance ticket booking precisely because it is the most beautiful bookshop in the world. The specific Porto street food experience — francesinha (a sandwich of cured meats and sausage, covered in melted cheese, then flooded with a tomato-and-beer sauce, served with chips) — is either revelatory or alarming depending on your relationship with excess, but it is impossible to understand Porto without eating one.

Coimbra is the city of Portuguese learning and the city whose specific culture — the black-caped students, the fado académico, the ritual of the Queima das Fitas — has no equivalent anywhere in Europe. The University of Coimbra was founded in Lisbon in 1290, transferred to Coimbra in 1537, and has occupied the hilltop above the city ever since: the oldest university in the Portuguese-speaking world, its academic traditions (the black capes, the coloured ribbons indicating faculty, the codes of student behaviour that govern everything from greetings to serenading) unchanged in their essential character since the 16th century. In 2013 the university and its associated historic buildings were inscribed as a UNESCO World Heritage site — not simply for the architecture but for the living academic culture they contain.

The Biblioteca Joanina (1728, Baroque, three interconnected halls of painted ceilings, gilded bookcases and 18th-century leather-bound volumes) is the most beautiful university library in the world: the specifically Portuguese Baroque of the João V period at its most exuberant, its three rooms ascending in elaborateness from the ground floor to the upper level, the ceiling of the top room painted with allegorical figures of the arts and sciences in colours that are simultaneously sumptuous and scholarly. The library's colony of bats — Egyptian free-tailed bats who emerge at night to eat the insects that would otherwise damage the books — is its most unexpected feature and has been documented since the 18th century. The Sé Velha (Old Cathedral, 1140, Romanesque, one of the best-preserved Romanesque cathedrals in the Iberian Peninsula) and the Monastério de Santa Cruz (1131, where the first two kings of Portugal are buried) complete the city's extraordinary medieval layering.

Fado de Coimbra — the specific tradition of the university city, distinct from Lisbon fado — is sung only by men (traditionally students and alumni), uses a different guitar tuning, and deals in the themes of academic life: nostalgia for student days, love affairs, the freedom of youth before the responsibilities of adulthood. The specific moment of the Queima das Fitas (May) — when final-year students burn the coloured ribbons that identified their faculty throughout their university career, symbolising the end of student life — is accompanied by fado performances that have an emotional charge unlike any other musical event in Portugal.

Braga is the oldest continuously occupied city in Portugal — established as the Roman Bracara Augusta in 15 BCE, capital of the Roman province of Gallaecia, then the first diocese in the Iberian Peninsula (4th century), then the seat of the Archbishops of Braga who contested political authority with the kings of Portugal from the 12th century onwards — and it has never quite lost the authority and seriousness that this history confers. It is also the most religious city in Portugal, the city where Holy Week processions are the most elaborate in the country, and the city whose specific relationship with the Minho landscape — rolling green hills, vineyards draped over granite pergolas producing Vinho Verde, the most refreshing white wine in the world — gives it a visual quality quite different from the drier south.

The Sé de Braga (Cathedral of Braga, begun 1070, the oldest cathedral in Portugal still in regular use) is a palimpsest of Portuguese architectural history: Romanesque nave, Gothic chapels, Manueline additions, Baroque organ cases (1738, two enormous carved wooden organs facing each other across the nave, the finest in Portugal), and the tombs of the first King of Portugal, Dom Afonso Henriques, and his mother, Dona Teresa — the foundational figures of the Portuguese nation, buried in a building that has been continuously maintained and modified for a thousand years. The Bom Jesus do Monte sanctuary (1784–1811, on a forested hill 5km from the city centre) is the most visited religious site in Portugal: a Baroque stairway of 577 steps ascending through chapels, fountains and viewpoints to a Neoclassical church at the summit, with the oldest surviving funicular railway in the world (1882, water-counterbalance mechanism, still operating) as the alternative ascent.

Vinho Verde — the young, lightly sparkling white wine of the Minho region, made from Alvarinho, Loureiro and Arinto grapes grown on the granite-based soils of the river valleys around Braga — is the most refreshing wine in Portugal and one of the most distinctive in Europe: lower in alcohol than most whites (8–11%), with a slight natural effervescence, pale green-gold in colour, tasting of citrus, green apple and the specific mineral quality of the granite terroir. The wine is best drunk young and cold at a restaurant terrace in Braga on a June evening, watching the cathedral light change across the square.

Faro is the capital of the Algarve — the southernmost region of Portugal, 300km of Atlantic coastline between the Spanish border and Cape St Vincent (the southwestern-most point of continental Europe, where the Portuguese navigators departed for their voyages of discovery in the 15th and 16th centuries) — and it is simultaneously a complete medieval city in its own right (the Cidade Velha, enclosed within Roman and Moorish walls, contains a Romanesque-Gothic cathedral, a bone chapel and a sequence of whitewashed streets that survive unchanged from the 16th century) and the gateway to the most spectacular coastal landscape in southern Europe.

The Ria Formosa Natural Park — a lagoon system of 60 kilometres stretching from Faro east to Cacela Velha, separated from the Atlantic by a chain of barrier islands (the ilhas barreira) — is one of the most important wetland ecosystems in Europe: the breeding ground for over 200 species of birds, the nursery for 50% of Portugal's commercial shellfish production, and a landscape of extraordinary visual serenity that bears no relationship to the tourist beaches of the western Algarve. The ferry network from Faro marina connects the city to the barrier islands (Ilha de Faro, Culatra, Armona, Ilha Deserta) in journeys of 15–40 minutes, each island with its own character from the fishing village of Culatra to the complete wilderness of the Ilha Deserta.

The Algarve coastline west of Faro — the Barlavento — contains the most photographed coastal scenery in Portugal: the Praia da Marinha (grottos, arches and sea stacks in amber limestone, accessible by cliff path from Lagoa), the Ponta da Piedade (the headland at Lagos, with sea caves and arches accessible by kayak at low tide), and the Praia de Benagil (the sea cave with a beach inside, the most reproduced beach photograph in southern Europe). The regional dish — cataplana (copper clam-shaped cooking vessel, filled with clams, white fish, shrimp, tomato, onion, peppers, chouriço and white wine, sealed and steamed) — is the finest expression of Algarvian cooking and the most appropriate meal for a salt-wind evening on a terrace overlooking the Atlantic.