Porto

Porto is Portugal’s second city and, in many ways, its soul. Where Lisbon is expansive and cosmopolitan, Porto is compact and defiant — a city of granite churches, blue-tiled facades, narrow medieval streets, and a relationship to its river and its wine that defines everything. The Ribeira district, stacked above the Douro, is a UNESCO World Heritage Site that looks like a painting: terracotta roofs, pastel buildings, laundry hanging from wrought-iron balconies, and the port wine lodges of Vila Nova de Gaia glowing on the opposite bank.

The Ribeira is where you start — the medieval riverfront quarter where the streets are so narrow the buildings lean toward each other and the restaurants set tables on every available square meter of cobblestone. Eat a francesinha — Porto’s signature sandwich, a construction of ham, sausage, steak, and cheese smothered in a beer-and-tomato sauce that should not work and absolutely does.

Vila Nova de Gaia — across the river — is where the port lodges have aged their wine for centuries. Graham’s, Taylor’s, and Ramos Pinto all offer tastings. The best view of Porto is from the terrace at Graham’s, a glass of tawny in hand, watching the sun set over the Ribeira.

The Livraria Lello is a bookshop so beautiful it allegedly inspired Hogwarts — a neo-Gothic fantasy of carved wood and a crimson staircase. Buy a book. It deserves it.

The Bolhão Market, recently renovated, is the city’s food heart: fresh fish, stacked cheeses, pastéis de nata from the bakery on the upper level.

São Bento Station — the main train station — has an entrance hall covered in 20,000 azulejo tiles depicting Portuguese history. It is the most beautiful commuter experience in Europe.

When to go: May to June or September. Porto is at its best in early summer when the days are long and the city fills with São João festival preparations (June 23-24), the wildest street party in Portugal.