PERCHED ON THE steep banks of the River Douro, Porto is a fascinating and charming city—easy to love, hard to leave. With its bustling back streets, Gothic churches, riverside cafes, and its long-standing trade in port wine, every turn reveals a different layer of history.

The historic center, a warren of narrow medieval streets, is a Unesco World Heritage Site, while the modern airport and affluent beachside suburbs firmly point to the 21st century.

This isn’t a city to rush. A comfortable pair of hiking shoes is recommended, as there are some steep climbs, but one of the joys of Porto is its relative compactness. Ditch the car and wander through this ancient city, where boutique art galleries rub shoulders with antiquated bookshops and washing hangs across narrow streets.

At times Porto can feel a little run-down, but that’s part of its charm—as is strolling by the river, discovering a medieval square or sitting in a café watching the world go by.

DAY ONE // FRIDAY