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From the enchanted rooftop world of the Duomo, you can see the graceful porticoes and ornate friezes of medieval Milan, Italy, fade into the sharp lines and angles of the modern city. It's a clear reminder that Milan isn't just a relic from the past. This magical yet understated city is bursting with a perfect mix of history, polished style and urban energy.

Although it's Italy's most prosperous city, Milan doesn't draw the tourists that may overrun Rome, Florence and Venice. But its streets are lined with famous sites, from the beloved opera house La Scala and the spired Gothic splendor of the Duomo to the beaux arts filigree of Galleria Vittorio Emanuele. Its museums and galleries hold many treasures, from Da Vinci's The Last Supper to Michelangelo's Rondanini Pieta.

And even when willowy models wearing the latest designer confections aren't rushing through the streets to get to casting sessions and runway shows, Milan is a powerhouse of smart, ubercool shops and trendy restaurants filled with dressed-to-kill locals, right in the heart of its ancient past.

Must See or Do

Sights—The Duomo and Piazza del Duomo; Galleria Vittorio Emanuele II; Leonardo da Vinci's famous work The Last Supper; the 15th-century Castello Sforzesco.

Museums—Pinacoteca di Brera; Museo Bagatti Valsecchi; Museo Poldi Pezzoli; Museo Teatro alla Scala; The Museo Nazionale della Scienza e della Tecnica Leonardo da Vinci.

Memorable Meals—Ingenious vegetarian fare at Joia; soaking up the ambience at Trattoria dei Cacciatori; hobnobbing with the glitterati at Trussardi alla Scala; fine dining at Cracco; affordable culinary perfection at Chic 'n' Quick.

Late Night—The Brera area; the Corso Como area; the Navigli area.

Walks—From the Duomo down Via Dante to the Castello Sforzesco, then to the castle grounds and through Parco Sempione; through the ultrachic designer area framed by Via Montenapoleone, Via Manzoni and Via della Spiga; along Corso Garibaldi between Via della Moscova and Via De Cristoforis and through the Porta Garibaldi arches.

Geography

As a glance at the map reveals, Milan radiates out from its amazing cathedral and the splendid Piazza del Duomo. A ring of streets, known as the cerchia dei navigli, marks the limits of the medieval city. Beyond that, another ring road—following the boundaries of more recent city limits—distinguishes central Milan from its outskirts.

Within the inner ring and northeast of Piazza Duomo are the chic shopping areas of Corso Vittorio Emanuele II and the area referred to as the Quadrilatero d'Oro ("Golden Rectangle"), bordered roughly by Via Manzoni, Via della Spiga, Via Sant'Andrea and Via Montenapoleone. West of the rectangle and behind La Scala—but still within the inner ring—is the chic area known as the Brera, surrounding the splendid art gallery Pinacoteca di Brera.

To the southwest of the city center lies the Navigli area. This area is named for the Naviglio Grande and the Naviglio Pavese, the two canals that were built so goods could be shipped to this landlocked city. The Naviglio Grande extends 30 mi/50 km to the Ticino River. The Naviglio Pavese provides a link to the city of Pavia, where the Ticino meets the Po River.

History

Milan's name is derived from Mediolanum, Latin for "middle lands"—an appropriate choice, as the city is located at the point where northern and southern Europe meet. It has a long history of changing governments, rulers and cultures. The original Celtic village became part of the Roman Empire around the first century BC; in AD 313 the emperor Constantine issued the Edict of Milan, making Christianity the official religion of the Roman Empire. After the collapse of the Roman Empire and centuries of barbarian rule, Milan once again became independent and prosperous as a city-state, rising to political and cultural prominence under the Visconti and Sforza families (considered among Europe's royalty) in the 13th and 14th centuries.

Milan's more recent history is no less turbulent. Spanish, French and Austro-Hungarian rule finally gave way to independence in 1861, when Milan became part of the Kingdom of Italy. The city was the birthplace of fascism in Italy in the early 20th century. Vestiges of that autocratic period survive today in its architecture; the massive Central Station is an excellent example.

After World War II, Milan drew workers from the poorer southern regions of Italy and overflowed its prewar borders to become a sprawling metropolis. In the 1970s and 1980s, the city prospered, becoming the industrial, financial, fashion and design center of the country.

Times have changed, however, as the world economy has inevitably slowed Milan's push to be one of the financial powerhouses of Europe. Even though some of the dazzle may be gone, the city maintains its head start on the rest of the country as its business sectors continue to bustle.

Potpourri

During the Middle Ages, the best ladies' hats were made in Milan. In English, the hat makers were called "Milaners," a term that eventually evolved into the term "millinery."

Cappuccino, or cappuccio as it is also called in northern Italy, is never sipped after a meal. It's a breakfast drink, drunk on an empty stomach. If you want to have it after a meal, you won't get arrested, but you will be a topic of conversation.

A number of mysteries surround The Last Supper, including the idea that the person to the right of Jesus is Mary Magdalene and not the apostle John. This proved inspirational to author Dan Brown, whose book The Da Vinci Code went on to sell more than 80 million copies worldwide.

When the city's various canals were eventually covered over, the bridges that spanned them were also removed. Only one remains. Called il ponte delle sirenette, "the bridge of the little mermaids," it found a new home in Parco Sempione when the canal it forded was closed in 1930.

All of the shops in the Galleria Vittorio Emanuele II are required to have signs in gold lettering on a black background.

In 1918, Ernest Hemingway was treated in Milan for wounds sustained on the front during World War I (he was an ambulance driver). At the Red Cross hospital on 10 Via Alessandro Manzoni, Palazzo Anguissola Antona Traversi (now the property of Intesa Sanpaolo bank), he met American nurse Agnes von Kurowsky; their courtship was the inspiration for the love story in A Farewell to Arms.

The first captain of the AC Milan soccer team and one of the founding fathers of Italian soccer was an Englishman from Nottingham, Herbert Kilpin. He led the team to three championship titles in the early 19th century and is buried in Milan's monumental cemetery. One of many amusing anecdotes about his career concerns his practice of leaving a bottle of whiskey in a hole dug behind the goal. That way, whenever he missed a chance to score, he could console himself with a stiff drink.

Gaspare Campari opened a bar (now Camparino in Galleria) in front of the Duomo in 1862, and there he sold his bitter aperitif. The recipe is a closely guarded secret, but the drink's bright red color comes from a colorant derived from the desiccated bodies of Mexican female cochineal insects.