Lisbon

Climb through the oldest neighborhood in Lisbon — a labyrinth of Moorish alleys that survived the earthquake that flattened everything else. From the castle ramparts to hidden viewpoints draped in bougainvillea, this is the Lisbon that fado was written to mourn.

7 stops · 80 min · 3.2 km

Walk the world's first earthquake-proof city grid — rebuilt from rubble by an iron-willed marquis — then climb through the literary quarter where the world's oldest bookshop sits next to a cafe haunted by Portugal's greatest ghost, Fernando Pessoa.

8 stops · 75 min · 3.5 km

Stand where Vasco da Gama set sail for India, taste the custard tart recipe monks sold to survive dissolution, and face the monument that celebrates — and uncomfortably glorifies — the empire built on what those ships found.

7 stops · 90 min · 4 km