The Ribeira district is the historic heart of Porto and the reason this city earned its UNESCO World Heritage status. Tumbling down the steep hillside to the banks of the Douro River, its narrow medieval lanes are lined with tall, crumbling townhouses painted in every shade of terracotta, ochre, blue, and faded rose. Laundry flutters from wrought-iron balconies above tiny taverns where locals nurse glasses of vinho verde, and the atmosphere is one of unpolished, deeply authentic charm. At the bottom, the broad Cais da Ribeira promenade opens up along the waterfront, where traditional rabelo boats once carried barrels of port wine downstream from the vineyards of the Douro Valley.

Across the river in Vila Nova de Gaia, the historic port wine lodges of Taylor’s, Graham’s, Sandeman, and dozens of others offer tastings and cellar tours that explain the centuries-old tradition of fortified winemaking. Connecting the two banks, the iconic Dom Luis I Bridge, an iron double-decker arch designed by a student of Gustave Eiffel, is one of the most photographed structures in Portugal. Walk across the upper deck for sweeping panoramic views, or stroll the lower deck at river level for a different perspective on the colorful Ribeira facades reflected in the water.

Pro tip: Take a six-bridges cruise on the Douro for about 15€, which takes you past all the major bridges and provides a magnificent riverside perspective of both Porto and Gaia. In the evening, grab a francesinha, Porto’s legendary meat-and-cheese sandwich drenched in spicy beer sauce, at one of the small local restaurants on Rua das Flores rather than the touristy waterfront spots.