10/20/2026
Most Portugal trips head straight for the Algarve. My favorite itineraries go almost everywhere else.
Lisbon: the natural first stop, with hilltop viewpoints, a world-class food scene, and the fairytale palaces of Sintra a short drive away.
The Alentejo: cork forests, sprawling w**e estates, whitewashed villages, and some of the darkest night skies in Europe. This is Portugal at its slowest and most soulful.
Comporta: rice paddies running into pine-backed Atlantic beaches, barely an hour from Lisbon. The understated coast Europeans have kept to themselves for years.
The Douro Valley: terraced vineyards stacked above the river, tastings at historic quintas, and lodges with valley views that stop conversation.
Madeira: dramatic cliff walks along centuries-old levada trails, a surprisingly serious dining scene in Funchal, and spring-like weather nearly every month of the year.
Wherever Portugal takes you, I'll make sure it goes past the obvious. Let's start planning.
