Regions to know
To frame your trip by what you have time for and what you're after.
Lisbon & Centro
Lisbon, Sintra, Cascais, Óbidos, Nazaré, Aveiro
Most flights land at Humberto Delgado (LIS). Use Lisbon as the base — Sintra (30 min by train), Cascais beach (40 min), Óbidos (1hr), Nazaré (1h30) are all day-trippable. Walkable, scooter-rental easy, public transit excellent.
Porto & Norte
Porto, Douro Valley, Braga, Guimarães
Porto as base. The Douro Valley wine country starts 90 minutes east — train to Pinhão, sleep at a quinta, take a Rabelo boat down the river. Braga has Portugal's oldest cathedral; Guimarães is the birthplace of the country.
Algarve
Lagos, Tavira, Sagres, Aljezur, Benagil
Southern coast. Lagos for cliff hikes (Ponta da Piedade), Benagil for the sea cave, Tavira for the calmer east. The west coast (Sagres, Aljezur, Carrapateira) is the wild, surf-and-cliff side — far better than the British-tourist resort strip in the centre.
Alentejo
Évora, Monsaraz, Elvas, cork-tree plains
The empty middle. Hour-after-hour of cork trees, olive groves, and whitewashed walled villages. Évora is the only town with a real tourist scene; the rest is for road-trippers and people who want wine and quiet. Best in spring (wildflowers) and autumn.
Madeira
Funchal, Pico Ruivo, levadas, Porto Moniz
Volcanic island 1,000km southwest of Lisbon. Funchal as base. Levada hikes (along ancient irrigation channels), the Pico Ruivo cloud-line sunrise hike, the natural lava pools at Porto Moniz. 5 days is the right add-on.
Azores
São Miguel, Pico, Faial, Terceira
Nine mid-Atlantic islands. São Miguel for the first visit (crater lakes, whale-watching). Pico for the climb of Portugal's highest peak (2,351m). Faial for the blue hydrangeas and the Horta marina (Atlantic crossing checkpoint). Weather changes every 20 minutes.