When most people think of Milan, minds wander to supernaturally beautiful women in gravity defying heels stomping down gleaming runways wearing the latest in Italian fashion. Versace, Valentino, Cavalli, Armani—all conjure up daydreams that Milan is just one giant catwalk. There is an idiom, “Florence has the David. Rome has the Pantheon. Milan has the clothes.” While Milan may be the fashion capital of the world, with the Quadrilatero della moda offering some of the most breathtaking window shopping imaginable, beneath the expertly styled and coiffed veneer lies an ancient city steeped in history and timeless splendor.

As Italy’s cultural powerhouse, Milan is a shocking juxtaposition of ancient and ultra-modern. Nowhere is this more obvious than at the very heart of the city. Perhaps Milan’s most famous site is the Duomo. This marble marvel is one of the largest churches in Christendom, losing out to St. Peter’s Cathedral in Rome only because the Church decreed that no other cathedral built was allowed to tower over the Vatican’s seat of power. It should be told that the size of their cathedrals are not the only thing the government capital and the business capital bicker about. The Milanese see the Romans as lazy, working governmental jobs that come equipped with short hours, frequent coffee breaks and three-hour lunches. Meanwhile, Romans dismiss Milanese as uptight workaholics with nothing else to live for.

Although the Duomo was consecrated in 1386, it wasn’t until the 19th century when Napoleon Bonaparte crowned himself the King of Italy that the façade was completed. Serving as the gateway to the Italian peninsula, Milan has found itself occupied by practically every invader in European history.

An overwhelming 3,500 statues call the Duomo their home, with roughly two thirds of them on the outside. But perhaps the most noted is the golden Madonna that graces the summit. She wasn’t added to the cathedral until 1774 and since then has been serving as the eternal matron of Milan, lovingly smiling on her people below. Inside the cathedral, above the chancel, the crucifix is said to contain a nail from Christ’s cross.

The Galleria Vittorio Emanuele II serves as Milan’s centerpiece. The two-winged glass-roof arcade was originally designed to connect piazza del Duomo with piazza della Scala. It is easily the world’s oldest shopping mall. Now it serves as Milan’s de facto downtown. Open 24 hours a day, the Galleria is the prime example of Milan’s time-is-money attitude. The massive floor mosaics represent the European, Asian, African and North American continents while the mosaics at the entrance arch are devoted to science, art, industry and agriculture.

Behind the Galleria, a statue of Leonardo da Vinci stands gazing at La Scala Opera House, arguably the world’s most famous opera house. Like most Italian cities, Milan is proud of the artists she produces and the statue serves as a reminder that da Vinci spent many years in Milan working for the Sforza family, who ruled Milan as the Medici family dominated Florence. Milan is home to one of da Vinci’s most famous works, the recently restored Il Cenacolo—The Last Supper. Da Vinci is appropriately attired; it is Milan after all, with his fashionable hydro-engineer hat, a testament to his re-engineering the city’s canal system complete with locks. Only two of these navigli (canals) remain navigable.

Another nod to Milan’s greatest artist-in-residence is the National Science and Technology Museum that boasts his name. This labyrinth of a museum is dedicated to an exhaustive display of technical skills, including printing, metallurgy, minting, engines as well as a computing section that shows the evolution of calculating techniques reaching from the abacus to the first IBM processor. The first floor gallery, also named after da Vinci, is a testament to his genius where reproductions of his sketches, including designs for flying machines and life size models, are housed.

Erected in the 1400s over the ruins of a castle-cum prison, Castello Sforzeco was designed by Francesco Sforza as both a defensive stronghold and an architectural eye-pleaser. Sforza was a condottiere, or hired mercenary. While the word “mercenary” has taken an unpleasant connotation today as a fighter for hire, during the Renaissance all of Italy’s great soldier-heroes were professionals hired by the cities that they served. Sforza is remembered as one of the greatest, most honest and most organized of the thousands of condottiere. Since the turn of the 20th century, the Castello has taken on a more peaceable function, serving as the storage facility for several city-owned antiquity collections. Michelangelo’s unfinished Rondanini Pieta sculpture, believed to be his last work, is housed there.

Milan is proud to focus on Italy’s future, but there are still remnants of the past that refuse to fade into the modern era. The narrow, winding streets of the Brera neighborhood, complete with cobble stone streets and low buildings, proudly represent the Italy that was. Most of the botanical wonders of the area’s hidden courtyards are private, but the Orto Botanico di Brera — a 54,000 square foot patch of park tucked behind the Pinoteca di Brera — remains Milan’s picture gallery. This former monastery houses Milan’s top collection of Italian paintings and was originally established in 1809 to preserve Napoleon’s looted art.

Milan has been referenced as the new buckle on an old boot. And although it can go cobblestone for cobblestone with other Italian cities, it is not known for its Roman ruins or fairy-tale feeling. The city’s sophisticated; urban style makes it proudly modern. Milan’s fútbol rivalry between the country’s two dominant teams, AC Milan and Inter Milan, could rival or even surpass the passion of the Red Sox-Yankee contention. Fútbol is more than a sport here—it’s a way of life. This fast-paced city doesn’t know the meaning of the traditional Italian siesta, making it feel more like New York or Paris than Italy. With as many banks as Rome has churches, Milan is flinging itself headfirst into the gotta-go feel of the new century.