Arrive in Lisbon and transfer from the airport to your hotel. The capital rises steeply from the Tagus, its tiled façades, tramlines and old neighbourhoods stacked across a series of hills. Praça do Comércio opens wide beside the river, while a few streets away Alfama folds back into lanes, stairways and small squares.

Follow whichever direction feels easiest after the flight. Baixa keeps things level, Chiado climbs gradually into cafés and bookshops, and Alfama is best approached without expecting the shortest route. Somewhere along the way, a yellow tram will probably appear at an angle that seems improbable even by Lisbon standards.

Leave Lisbon for Sintra, where forested hills hide some of Portugal’s most imaginative architecture. The vivid towers and terraces of Pena Palace seem to borrow from several architectural traditions at once, while Quinta da Regaleira turns gardens, tunnels, towers and stone stairways into something altogether stranger. The journey then continues to Cascais, bringing a change of scene before returning to Lisbon.

Spend the last night in the capital around Príncipe Real or Chiado, where restaurants and cafés sit comfortably among old façades and lively streets. Sintra has a habit of making normal architecture look rather restrained afterwards.

Portugal’s central region brings together some of the country’s most significant religious landmarks, dramatic Atlantic scenery and beautifully preserved medieval towns. Visit the Sanctuary of Fátima, continue to the magnificent Batalha Monastery and stop in Nazaré, where the old fishing town meets a spectacular coastline shaped by the Atlantic.

The final stop is Óbidos, a charming walled town filled with whitewashed houses, cobbled lanes and centuries-old architecture. Take time to wander through its historic centre before returning to Lisbon, bringing together a day of culture, history and some of Portugal’s most distinctive landscapes.

Travel south by train from Lisbon to Faro, arriving in the Algarve’s understated capital. Whitewashed buildings, quiet squares and the old walled quarter give Faro a more intimate scale, with the marina and lagoon sitting close to the historic centre.

As evening settles, listen to Portuguese Fado accompanied by Port wine. A singer, a Portuguese guitar and a room prepared to listen are often all the music requires. Afterwards, Faro’s old lanes are particularly pleasant beneath the lamps, when the daytime traffic has thinned, and the small squares belong mostly to dinner tables.

Spend the day exploring the Algarve through Benagil Cave, Praia da Marinha, Carvoeiro and Algar Seco. Limestone cliffs rise above intensely blue water, beaches sit tucked between rock walls, and natural arches and caves punctuate the route. Carvoeiro brings a lived-in coastal town into the mix before Algar Seco returns you to the cliffs and their winding formations.

Back in Faro, the marina makes an easy place for a walk before dinner, or slip through the archways into the old town and choose a table somewhere inside the walls. After several hours out on the Algarve, a quiet night feels entirely sufficient.

Leave Faro by train and travel north to Porto. Granite buildings and blue-tiled churches replace the Algarve’s pale southern palette, while steep streets drop towards the Douro and the closely packed houses of Ribeira. Porto wears its age openly, with weathered façades standing beside some of the country’s grandest civic and religious architecture.

Walk down towards Ribeira once you have settled in, then cross the Dom Luís I Bridge if you feel like seeing the city from Vila Nova de Gaia. Porto is particularly handsome towards dusk, when the façades opposite catch the last light and tables begin filling along the quay.

Travel into the Douro Valley, where vineyards climb in terraces above the valley floor and wine has shaped both work and life for generations. Tastings and a local lunch form part of the day before you board a Douro River cruise, passing slopes planted almost to their upper edges, small settlements and estates tucked into the folds of the hills.

Return to Porto for the last evening of the journey. Ribeira is lively after dark, while Vila Nova de Gaia offers the opposite view across to the old city. The bottles on the table need little introduction now; you have spent the day among the vineyards they came from.