The country’s main airports are in Milan and Rome. Over the past few years, airlines like Norwegian and Turkish Air have run outrageous deals if you fly through their hubs so if you can find a short hop into Italy from Oslo or Istanbul, it may be well worth the discount. Also look for airlines like SAS, KLM, and Swiss.
Italy has a very well developed and fairly reliable rail system that will get you to most towns of note without much delay but the rise of budget airlines means that flying between cities can be just as cheap. But if you want to tour the countryside you’ll still need a rental car.
Rome is the obvious starting point for culture vultures because it’s drenched in ancient, medieval, papal, and modern history. But Italy also has a tremendous musical footprint that comes alive most vividly in opera. Milan and Venice contain two of the greatest opera houses in the world in La Scala and La Fenice, respectively. Most cities of note, like Bologna and Palermo, contain dynamic opera houses which thrive on repertory and contemporary experiments.
Check out Siena’s summer Palio, a medieval horse race around the city’s central piazza. It’s full of pomp and fanfare—but go prepared, not an ounce of it is sanitized; jockeys are regularly injured, horses even more so. A similar race is held annually in Asti. In Venice, the annual carnival is enticing fun, with all those masks and Baroque plays. And the Venice Biennale, every two years, is a must-see for contemporary art lovers. Don’t forget that Italy is mad for soccer, so if you’re there during the regular season (roughly September through May), seek out a game to experience all the passion and fraternity. It’s even better when events like the European Cup or World Cup are being played; every bar or café will be full of fans.