Two weeks is the length at which Portugal stops being a city break with excursions and becomes a country. It is small enough that you can cover the mainland properly in fourteen days, and varied enough that the coast, the vineyards, the plains and the two big cities feel like different places. The way to waste that fortnight is to book eight hotels and spend the days on motorways. Here is a route built around four or five bases, with the train doing the long legs and a car for the parts where the road is the point.
The shape
Lisbon, four nights. The city and its day trips.
The Alentejo, two or three nights. The plains inland: cork oaks, walled towns, wine and the emptiest roads in the country.
The Algarve, three nights. One base, driving out to the coves.
Porto, three nights. The city, the lodges and the river.
The Douro, two nights. The terraced valley upriver, which is the quiet highlight.
That is fourteen nights with four moves, and it can be reordered to suit your flights.
Lisbon and its day trips
Give the city two full days for the neighbourhoods, the viewpoints, the trams and the food.
Sintra takes one, and it needs booking rather than improvising, since the main palaces run on timed slots that sell out.
A second day trip from the coast or the walled towns north of the city.
No car in Lisbon. The metro, the trams and your feet are better, and parking is a problem you do not need.
The Alentejo
This is the leg most itineraries skip and the one people come back talking about.
Pick up the hire car as you leave Lisbon, not before.
A walled town base, from which the region is a series of short drives through cork oak and wheat.
The roads are empty, the light is enormous, and the towns are white and quiet.
The food is heavy and excellent, built on bread, pork and herbs, and it costs very little.
It is hot in summer, genuinely, with very little shade.
The Algarve
One base for three nights, not two bases, since the region is narrow and everything is within an hour.
Choose the town deliberately, because the resort towns and the working city at the eastern end are completely different holidays.
Take a boat trip along the cliffs, since the caves and arches cannot be reached from land.
Keep the car for this leg, which is what makes the coves reachable.
Porto and the Douro
Drop the car before Porto, or park it for the duration, since the city is dense and steep.
Three nights in Porto covers the city, the port lodges across the river and a proper wander. Our one-day Porto itinerary shows the routing that only climbs the hill once.
Then the Douro, upriver, either by train along the water, which is one of the great European rail journeys, or by car on the valley roads.
Two nights in a quinta among the terraces is the slow end the trip deserves.
Getting between the legs
Lisbon to Porto is a fast, comfortable, frequent train and it beats driving comfortably.
Lisbon to the Algarve is a train or a short flight, and a drive if you are coming via the Alentejo.
The Douro line from Porto follows the river and is worth taking for its own sake.
Local buses fill in the gaps in the regions.
Our guide to transport in Portugal covers the ticket types, the tolls and when a car is a liability.
Adjusting the route
Less driving? Drop the Alentejo, extend Lisbon and Porto, and go to the Algarve by train.
More coast? Trade the Alentejo for the west coast and the surf towns.
Only ten days? Cut the Algarve entirely and keep Lisbon, the Douro and Porto, which is roughly the shape of our one-week Portugal itinerary with breathing room.
Islands? Madeira and the Azores are separate trips with their own flights and do not belong in this fortnight.
The short version
Use four or five bases across fourteen nights and no more, with at least three nights each in Lisbon and Porto. Take the train between the two cities and hire a car only for the Alentejo, the Douro roads and the Algarve. Book an open-jaw flight so you never double back. Give Sintra a booked day and the Algarve a single base with a boat trip. Finish in the Douro valley among the terraces, which is the leg nobody plans enough time for and everybody remembers.
