Trieste rewards slow exploration. The city's layered Habsburg, Roman, and Italian identity is written into its architecture — from the monumental Piazza Unità d'Italia facing the sea, to the Roman theatre tucked behind the cathedral hill, to the white neo-Gothic Castello di Miramare on the coast. For literary travellers, Trieste holds a special significance: James Joyce lived here for much of the decade between 1904 and 1915, teaching English and writing, and traces of his presence remain throughout the city.
Set aside one day for the centre — the piazza, the Canal Grande, the cathedral hill, the Joyce trail — and a second for an out-of-centre trip to either Miramare or the Risiera di San Sabba. Don't try to combine those two in a single afternoon.