Livorno

Livorno is the Tuscan coast you don't expect: Medici-founded in 1577 as Nova Civitas, planned from scratch by Bernardo Buontalenti as a free port to rival Genoa and Venice, and unique among Tuscan cities for being entirely a Renaissance-era invention rather than a medieval inheritance. The original pentagonal city walls enclosed a Venetian-style quarter (Venezia Nuova) laced with navigable canals where merchant warehouses opened directly to the water — Jews, Greeks, Armenians, English, Dutch and North Africans were all invited to settle under the 1591–1593 'Livornine' laws granting freedom of worship and trade, making Livorno the most cosmopolitan port on the Mediterranean for two centuries. What you see today: Fortezza Vecchia (1521) and Fortezza Nuova (1590) guarding the inner harbour; the four bronze Moors (1626) chained to the base of Ferdinando I's monument facing the port; the Terrazza Mascagni (a 1925 Art Deco chequerboard promenade with 4,100 black-and-white tiles facing the Tyrrhenian); the Cattedrale rebuilt after 1944 bombing; the Pentagono di Buontalenti street grid still visible from above.

The Macchiaioli painters' movement was born here in the 1860s (Fattori, Lega, Signorini all lived and painted the local light). Modigliani was born in Livorno in 1884. And the food: cacciucco — a 5-fish stew with toasted bread and red wine, the city's totemic dish — plus ponce alla livornese (rum-spiked coffee) at the Caffè Civili. The Tuscan archipelago (Capraia, Gorgona, Elba) ferries out from the port within view of the promenade.