Italy

Italy’s great trick is that it never feels like one place. The brisk efficiency of Milan has almost nothing in common with the languid chaos of Naples. A Piedmontese truffle risotto and a Sicilian arancino are both Italian in the way that a sonnet and a shout are both language — technically the same category, spiritually different planets. This is what makes Italy inexhaustible. You could visit for thirty years and still find a valley in Basilicata or a hill town in Le Marche that rearranges your understanding of what this country contains.

The south is where Italy becomes most itself. Puglia’s masserie and olive groves, the volcanic strangeness of the Aeolian Islands, the Baroque excess of Lecce — these places carry none of the tourist infrastructure of Tuscany and all of the raw, unmediated character that infrastructure tends to smooth away. Emilia-Romagna deserves a trip built entirely around eating: Parmigiano in Parma, balsamic in Modena, tortellini in Bologna, each town fiercely protective of its contribution. Even Rome, which can feel exhausting in its density of wonders, rewards the visitor who wanders past the obvious — into Trastevere at dusk, into the Aventine Hill’s keyhole view, into a trattoria in Testaccio where the menu has not changed since 1960.

When to go: April to early June or mid-September through October. Italian summers are hot, crowded, and increasingly punishing in the south. October in Piedmont or Umbria — fog, truffles, new wine — may be the most underrated month in European travel.

What most guides get wrong: They concentrate on the north and center. The Mezzogiorno — Naples, Calabria, Sicily, Puglia — is rougher, less polished, and vastly more interesting than most itineraries suggest. Also: eat where Italians eat, not where the menu is in four languages. The difference is not subtle.