Climbing to the roof of the Duomo
The roof of the city's principal landmark gives you an eagle-eye view over the busy streets and alleys downtown. More importantly, this is where you can get up close and personal with the sculptures of saints and spookily realistic gargoyles, who are also keeping tabs on deeds good and bad of the inhabitants below.
Window shopping for a sleek home
Milan is the modern furniture capital of the world, a superlative that is a lot more fabulous than it sounds once you see the latest designs. There's no better way to immerse yourself in the height of hipness than peering through the store windows along Via Durini, metaphysically reclining on ergonomic sofas, while drawing the lines of the next Alfa-Romeo under the spotlight of the sleekest of lamps.
Taking in a match at San Siro
This is Italy's cathedral to calcio, or football, and home to two of the nation's top teams, Inter and AC Milan. Tickets are scarce when the two play each other in the derby, but there are usually dozens of opportunities in the cooler months to put on the team's colors and make the pilgrimage to one of the most venerated stadiums in the world. Beware: fans can be rowdy so families should definitely stay away from the mobs behind either goal, known as the curve.
The aperitivo hour
They don't call it Milano da bere ("Milan in a glass") for nothing. This city celebrates the art of the cocktail with free finger food and pasta starting around 5pm until people get hungry for a real dinner at about 7pm. A few of the more hopping venues are Le Biciclette (via Conca del Naviglio 10), Victoria Cafe (Via Clerici 1) and really anywhere in the Brera district. The free food is not as remarkable as the people-watching and the Campari-based cocktails.
Hear the 'fat lady sing' at La Scala
This is the apex of Italian opera, and the audience at Teatro alla Scala expects the very best, every night. Tickets for opera performances go on sale about two months in advance and are in high demand; it is easier to catch a concert or ballet. What you see on the stage may not even matter: One of the most memorable parts of the experience is taking in the grandeur of the interior and the elegance of its guests.
Fashion shopping in the 'Golden Triangle'
This neighborhood around Via della Spiga and Via Manzoni is the number-one destination for most tourists in Milan. Pack your plastic and fill up your bags at big names like Armani, Cavalli, Valentino, and Versace, but don't miss out on some of the smaller, less-crowded boutiques on nearby Via Solferino, or in the southern quarter of Porta Ticinese.
The majesty of the lakes
If you have an extra day in Lombardy, a day trip to Lake Como is nearly obligatory. The heart-stopping scene of Alpine slopes crashing into the cobalt water, whose coastline is studded with medieval burghs such as Bellagio and ringed by palm trees and bougainvillea, is unique in the world. Small wonder that superstars from Versace to Clooney have chosen this backdrop for their second (or third) homes.
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