Livorno, Civitavecchia, Valencia

Purpose-built as a Medici utopia in the late sixteenth century, Livorno was conceived from the outset as a city without discrimination — its founding Leggi Livornine granted equal rights to Jews, Christians, Muslims, and merchants of every nation, making it one of the most cosmopolitan cities in Renaissance Europe. Today, the Venetian-style canals of the Venezia Nuova quarter reflect colourful palazzi with a distinctly faded glamour, while the Mercato Centrale's fish counters display the cacciucco ingredients — a robust Livornese brodetto of five sea creatures — that make this port city a pilgrimage for serious eaters. Day trips to Pisa and Lucca are effortless from here. The season runs April through October.

Rome's ancient maritime gateway since the Emperor Trajan commissioned its harbour in 106 AD, Civitavecchia is the natural prologue to the Eternal City — just seventy minutes southeast by express rail. The port's Renaissance fortress, designed in part by Michelangelo, anchors a working waterfront that has welcomed travellers for millennia. Beyond Rome's unmissable monuments, consider an afternoon in the Civitavecchia thermal baths, drawing on mineral waters prized since antiquity. Spring and autumn offer the ideal balance of mild weather and manageable crowds for exploring the capital's layered history.

Valencia, Spain's luminous third city, dazzles with a creative energy anchored by two thousand years of layered civilization — Roman foundations, Moorish irrigation gardens, a Gothic cathedral housing what many believe to be the Holy Grail, and Santiago Calatrava's futuristic City of Arts and Sciences gleaming beside a park-filled riverbed. The city invented paella over an open fire of orange-wood in the surrounding huerta, and the Las Fallas festival each March — when neighborhoods compete to erect and then ceremonially burn towering satirical sculptures — is one of Europe's most spectacular celebrations. Valencia's Mediterranean climate makes it exceptional year-round.