Portugal is 560km long and 220km wide at its broadest. This sounds manageable and, in the best sense, it is. What the dimensions contain — two Atlantic coastlines with completely different personalities, the cork-oak and olive plains of the Alentejo, the Douro wine terraces, the granite-and-gold city of Guimarães where Portugal was born as a nation in 1143, the medieval walled town of Óbidos — is considerably more generous than the map suggests.

The 14-Day Route

Days 1–3: Lisbon. Base yourself here to start — see the city properly (Alfama, São Bento station, Belém, Mouraria for dinner) and do Sintra as a day trip by train on a weekday before the crowds. This is not the driving part; take public transport.

Days 4–5: Setúbal and the Arrábida Coast. Collect the rental car on day four. Drive south across the Tagus (use the 25 de Abril bridge — the views are worth it) to the Setúbal peninsula. The Arrábida Natural Park coast — Portinho da Arrábida, Praia de Galapinhos — has turquoise water and limestone cliffs. Swim in the morning, eat grilled fish in Setúbal for lunch, drive on to Comporta (the low-key coastal village that wealthy Lisboetas keep quietly to themselves) for the night.

Days 6–7: Alentejo Coast and Sagres. South along the Costa Vicentina — stop at Praia de Odeceixe (a river-meets-sea beach of unusual charm), continue to Sagres at the south-western tip of the continent. Walk the headland at Cabo de São Vicente, where the lighthouse sits on the most south-westerly point of continental Europe and the wind comes straight from the open Atlantic. Spend a night in Sagres or the slightly more amenable Vila do Bispo.

Days 8–9: The Algarve. Drive east along the southern coast. Stop at Praia da Bordeira for the spectacular beach, at Lagos for the Ponta da Piedade sea caves (book a kayak tour), at Praia da Marinha for the clifftop walk. Skip Albufeira unless you need a supermarket. Continue to Tavira in the east — the most Portuguese town on the coast — for your second night.

Days 10–11: Évora and the Alentejo Interior. Drive north from Tavira into the Alentejo — a different country in all but name, with white-washed plains and megalithic stone circles older than Stonehenge. Évora is the region's capital: a UNESCO-listed historic centre with a Roman temple, a medieval cathedral and the frankly arresting Bone Chapel (Igreja dos Ossos), whose walls are lined with the bones of 5,000 Franciscan monks. Outside the city: Herdade do Esporão for a winery tour and tasting (€15–25, book ahead), and Monsaraz — a fortified medieval village above a reservoir, with views into Spain and a population small enough that you can hear silence.

Book Alentejo wine tours and Évora guided experiences — the best winery tastings require advance reservations.

Days 12–13: Douro Valley

Drive north through the Alentejo and into the Douro wine country — the landscape changes abruptly around Régua as the schist terraces begin and the valley narrows. Pinhão, in the heart of the port wine country, is the best base. The train station at Pinhão is papered in azulejo panels depicting the grape harvest; the village itself is small and practical. From here, drive the N222 road along the south bank of the Douro — named by a motoring organisation in 2015 as one of the most scenic driving roads in the world, a designation it earns every kilometre. Stop at Quinta do Crasto or Quinta do Vallado for a tasting (book ahead; €15–30). Stay overnight in Pinhão or at one of the valley quintas for the dawn light on the terraces.

Day 14: Porto and the Return

Drive west along the Douro to Porto (90 minutes). Return the car — Porto's historic centre is not a place you want to drive; park at the airport or a peripheral garage and take the metro. Spend the afternoon at São Bento station and the Dom Luís bridge. Return from Porto airport, or take the train back to Lisbon and fly from there.

Driving Portugal — What They Don't Tell You

  • Electronic tolls: All Portuguese motorways use the Via Verde electronic system. Rental cars without a transponder will have tolls billed against your credit card — or, if the system misses them, arrive as fines weeks later. Ask your rental company explicitly before departure. A Via Verde transponder or Toll Pass costs approximately €2/day to rent.
  • The EN2: Portugal's longest national road, 738km from Chaves in the north to Faro in the south. It is the scenic alternative to the motorway system — slower, but through the country rather than above it.
  • Petrol: Portugal uses unleaded (gasolina sem chumbo) and diesel (gasóleo). Prices run approximately €1.70–1.90/litre for unleaded. Supermarket fuel stations (Pingo Doce, Continente) are consistently cheaper than motorway stops.
  • Parking in cities: Paid and metered in all city centres. Blue zones require a disc or meter. Underground car parks (parkings) are the cleanest solution and run approximately €1.50–2.50/hour.