Portugal is small on a map and slow on the ground. Porto to the Douro's Pinhão is roughly two hours by road, Lisbon to Évora about ninety minutes, and Lisbon to the Douro closer to three and a half hours. Any itinerary that tries to join the Douro, Alentejo and the Atlantic coast in under a week spends most of its time in transit, which is why our own journeys run ten to eleven days.
Season matters more than region. Harvest in the Douro usually begins in late August and runs through September, when the quintas are working and the lagares are treading at night; it is the most atmospheric time to visit and the hardest time to book. Spring, from late April into early June, gives green terraces, open cellar doors and unhurried winemakers. July and August are hot inland — the Alentejo regularly passes 38°C — and the coast is busy.
Allow three days for the Douro if you want more than a boat trip and two tastings: one for the Cima Corgo quintas around Pinhão, one for the higher Douro Superior, and one for Porto's Vila Nova de Gaia lodges, where the ports are aged and blended. Two to three days suits the Alentejo — Évora as a base, with Monsaraz, the marble towns and the amphora-wine producers within an hour. Add two days for Lisbon, Sintra and the Setúbal peninsula, where Moscatel and old-vine Castelão are made within sight of the estuary.
Book tastings ahead. Most serious Portuguese producers are family-run and receive visitors by appointment only; walk-in tasting rooms are the exception, not the rule. Lunch is the day's main meal and cellar lunches routinely run to three hours, so plan two winery visits a day, not four.
Driving is straightforward but the Douro's terrace roads are narrow, steep and unforgiving after a tasting. If you would rather not drive, travel with a group that provides a driver — that is exactly why our own tours move in one microbus with a single driver and a fixed, unhurried rhythm.