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Few Italian cities carry quite the same weight of accumulated history as Trieste. Perched at the far north-eastern tip of the Adriatic, where the Karst plateau drops sharply to the sea and the borders of Slovenia and Croatia press close, it spent centuries as the principal port of the Habsburg Empire before finding itself, after the Second World War, in a peculiar limbo that lasted until 1954. That layered past, Austrian, Slovenian, Italian and Jewish communities folding into one another across the same streets, gives Trieste a character unlike anywhere else in the peninsula. The coffee culture alone signals the difference: the city has its own vocabulary for ordering espresso, and its historic caffès, including the celebrated Caffè San Marco on Via Cesare Battisti, were once the working rooms of James Joyce, who lived here for more than a decade and drafted much of Ulysses in the city.

The waterfront is where Trieste announces itself most forcefully. The Piazza Unità d'Italia, one of the largest seafront squares in Europe, opens directly onto the Gulf of Trieste with a grandeur that feels more Central European than Mediterranean. Behind it, the Canal Grande cuts into the old city, and the hillside district of San Giusto rises above the Roman forum ruins to the cathedral and castle that share its summit. The Borgo Teresiano, the rational grid laid out under Empress Maria Theresa in the eighteenth century, contains the densest concentration of coffee houses, bookshops, and the kind of unhurried civic life that rewards an afternoon on foot.