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Livorno sits on the Tyrrhenian coast of Tuscany with a directness that sets it apart from the region's more celebrated hill towns. Where Siena and San Gimignano trade on medieval towers and Renaissance piazzas, Livorno was largely a planned city, laid out from the late sixteenth century under the Medici grand dukes as a free port open to merchants, Jews, Greeks, Armenians, and Protestants at a time when such tolerance was rare in Europe. That cosmopolitan founding left a permanent mark on the city's character: the cooking is bolder and more maritime than inland Tuscany, the dialect is famously blunt, and the residents carry a civic pride that has little interest in performing itself for visitors.

The Venezia Nuova quarter is the most immediately striking part of the old city, a grid of canals cut through the urban fabric so that boats once delivered goods directly to warehouse doors. The waterways are narrower than those of Venice and the buildings plainer, but the effect is quietly compelling, particularly in the early morning when the light off the water catches the ochre and terracotta of the facades. The Fortezza Nuova sits on an island within this canal network, its grassy interior now used as a public park rather than a military installation. A short walk away, the Fortezza Vecchia guards the harbour mouth, its foundations incorporating a medieval tower that predates the Medici city entirely.