Portugal packs an enormous variety into a small country. The classics are classic for good reason, but even well-trodden ground is worth your time.
Lisbon is one of Europe's most liveable and walkable capitals. The Alfama district, Belém's monastic architecture, the tram-laced hills, the fado bars open until 2am — it rewards time spent simply wandering. The food scene has grown considerably; the older tascas and the newer natural wine bars are both worth your attention.
Porto is smaller, grittier, and increasingly fashionable. The Ribeira riverfront and the azulejo-tiled churches are the postcard images, but the city's energy comes from its bookshops, its music venues, and the port wine lodges of Vila Nova de Gaia just across the Douro. Don't skip the Livraria Lello — the queue is worth it.
The Algarve remains the country's beach destination: limestone cliffs, sheltered coves, and long sandy stretches. Lagos, Praia da Rocha, and Armação de Pêra are the main resort centers; the western Costa Vicentina, within the natural park, is wilder and far less developed.
Sintra — a 40-minute train ride from Lisbon — is a UNESCO-listed hillside town of palaces and forested gardens. It gets very crowded in summer; go early or come in the shoulder seasons.
Évora is the best base for the Alentejo region: a walled Roman city with a cathedral, an intact temple, and a chapel lined with human bones. The surrounding plains produce some of Portugal's best wine and olive oil.
The Douro Valley is Portugal's wine country proper — terraced vineyards descending to a green river, best seen from the water or on foot. Take the train from Porto to Peso da Régua for some of the most dramatic rail scenery in Europe.
Madeira and the Azores are both worth the flight. Madeira offers dramatic volcanic scenery, levada walks, and a subtropical climate. The Azores — nine islands spread across the mid-Atlantic — are rawer and less visited, with volcanic calderas, whale watching, and a palpable sense of being off the beaten track.
Coimbra has one of Europe's oldest universities and a medieval upper town that rewards a half-day at minimum. The university's baroque library is genuinely extraordinary.
Braga is Portugal's religious capital and one of its most dynamic smaller cities — a good base for the Minho region and the sanctuary of Bom Jesus do Monte.