Story by Clodagh Kinsella | Photography by Susan Wright | Hemispheres, September 2014

Italy's financial hub may not have the historical flourishes of cities like Rome, Venice and Florence, but scratch its famously stylish surface and you'll find a wealth of world-class art, architecture and design

Moneyed, modern and relentlessly chic, Milan can seem a little un-Italian to the first-time visitor. Large swaths of the city were rebuilt after World War II, so it lacks the sheer concentration of historical landmarks found in other Italian destinations. As a local saying has it: “Rome is a voluptuous woman whose gifts are very apparent, while Milan is the shy, demure girl whose treasures are plentiful but discovered in time."

“Shy" might be pushing it, but Milan's businesslike facade does mask a rich past. Founded in 400 B.C., this former capital of the Western Roman Empire has been reshaped by a procession of rulers, from the Viscontis, beginning in the 13th century, to Mussolini in the 20th—influences marked by the Gothic spires of the Duomo and the blunt Rationalism of the Triennale. You'll find many beautiful architectural landmarks as you make your way around Milan—if you can drag your eyes away from the beautiful people.

Mostly, of course, Milan is celebrated for its style—its fashion weeks showcasing storied labels like Armani and Prada, and the Salone del Mobile furniture fair. As one of the “big four" fashion capitals, Milan boasts unrivaled luxury shopping in plush enclaves like the Quadrilatero della Moda. It's not surprising, then, that this multifaceted city is set to host the 2015 Universal Exposition: technology, culture, creativity and tradition are subjects Milan knows well.

DAY ONE | For centuries, the Virgin Mary atop the Duomo dominated Milan's skyline, but from your suite at Palazzo Parigi, you look out on a new kind of iconography: the high-concept skyscrapers of the Porta Nuova business district. Your hotel goes a more traditional route. Situated in a 17th-century palace, it was transformed over the last five years into an imperial property strewn with antique statuary, elaborate chandeliers and acres of Carrara marble.

Breakfast arrives on wheels. You pick at slivers of exotic fruit and a delicate omelet on your private terrace, and then prepare yourself for a crash course in Milanese design. You've opted to get around today on the back of a slick Garibaldi 71, rented from storied bicycle maker Rossignoli. At the company's Brera store, fifth-generation scion Matia Bonato uses a 20-foot pole to pluck the bike from a lofty ceiling rack. “It's not about strength," he says, “but technique."

A streetcar in artsy NavigliA streetcar in artsy Navigli

From here, you judder over cobblestones to Parco Sempione, where you pause to take in the sprawling 15th-century fortification Castello Sforzesco and the 19th-century Arco della Pace. You lock your bike at the foot of Torre Branca, the 350-foot steel-tube viewing tower designed by architect Gio Ponti for the 1933 Triennale. “You know Santa Maria delle Grazie, where they keep 'The Last Supper'?" says the elevator operator on the way up. “My local church."

At the Triennale museum next door, there's more ingenious Italian design on display, including the Olivetti typewriter and the Bialetti stovetop espresso pot. You pay homage to the latter with a coffee overlooking the sculpture garden. Giorgio de Chirico's hypnotic “water-parquet" installation leaves you a little woozy, so you decide to move on to a more utilitarian form of design.

Studio Museo Achille Castiglioni, honoring the inventor of the swooping 1960s “Arco" floor lamp, is less museum than time capsule—its tractor-seat stools, arch-lever files and quirky cutlery left untouched since the designer died in 2002. “I had a terrible childhood," says the designer's daughter, Giovanna, your tour guide. “Because my father loved everyday objects, he always stole my toys." She pulls out a VLM light switch, Castiglioni's ubiquitous design. “He'd carry it around in his pocket. You'd always know where he was by the clicking."

You trade your bike for the metro and emerge in Zona Tortona, a former industrial district that's reinvented itself as a design mecca, home to Armani's head offices and the famous furniture fair. You navigate its narrow, graffitied streets in search of Da Noi In, which is known for its inspired seafood dishes. In a stunning outdoor courtyard, you sample a platter of house-smoked swordfish, tuna and salmon, served with Ligurian olives, followed by aromatic potato gnocchi in a bright basil cream.

Modern designs at the Museo Achille CastiglioniModern designs at the Museo Achille Castiglioni

A postprandial stroll through bohemian Navigli, with its network of canals—the highway system of medieval Milan—makes room for dessert: an apricot gelato from the artisanal chain Grom. From here, you veer north to slow food mall Eataly, where you join shoppers browsing three floors of giant hams, vats of olive oil and chocolate waterfalls, or mainlining piadine flatbread in the eateries along its perimeter. You nurse a prosecco, serenaded by a trio of electric guitarists with gray Afros and a liberal approach to the question of tone.

Next, you stroll down the pedestrian shopping strip Corso Como, emerging into Piazza Gae Aulenti, Porta Nuova's central plaza, which—a plaque informs you—is meant to serve as a contemporary Roman forum. Eyeing the undulating UniCredit Tower, a young man in front of you cries: “I feel nothing!" Judging by the square's many pop-up bars, and the happy chatterers therein, he's in the minority.

An endless elevated walkway deposits you at Ristorante Berton, Friuli-born chef Andrea Berton's sleek testament to restraint. Surrounded by men in thick-rimmed glasses (a Fashion Week hangover), you polish off six first-rate courses, including a dish of baby scallops and licorice that resembles a Yayoi Kusama dot painting. And that, you decide, is enough conceptual flair for one day. You head back to your hotel and the soothing strains of classical piano drifting through the lobby.

The Triennale's kaleidoscopic tower

The Triennale's kaleidoscopic tower

DAY TWO  | Milan's status as a design capital doesn't just rest on skyscrapers and showrooms; its historic monuments were just as innovative in their day. This classical spirit drives you to the iconic Pasticceria Marchesi, which has been serving up pastries since 1824. Following tradition, you settle up first, then wait as an angelic white-haired lady hands you cannoncini—cream-filled puff pastry horns. At the café's tiny bar, women with la Rinascente shopping bags drown out the clink of porcelain, nibbling their confections with a restraint you can't muster.

Sugar level high, you speed-shuffle down Corso Magenta to Santa Maria delle Grazie, home to “The Last Supper," or “Il Cenacolo"—Leonardo da Vinci's depiction of Christ breaking bread and brokering betrayal. Your guide, Alice, who runs Viator's art tour, steers you through the Dominican convent's hidden cloister. You spot a monk in flowing white robes studying a Bible. “They always tell me I should talk less and pray more," says Alice in a respectful whisper.

Hushed reverence seems the apt response as you stand before the painting. Unlike the fresco opposite, Leonardo's work was applied directly onto dry wall, which is the reason for its fragility (and your 15-minute viewing slot), but also for its celebrated vividness. You note how light from the refectory windows suffuses the painting's edge, seeming to expand the room's dimensions. Alice nods and says, “It's the Renaissance doing 3-D."

Art and religion also intersect at San Maurizio al Monastero Maggiore, whose low-key exterior belies the splendor inside: a seamless patchwork of luminous 16th-century devotional paintings. Next, you make your way to the dazzling Santa Maria presso San Satiro, off Via Torino, whose sole devotee is a businessman, head bowed, a briefcase at his feet. Your final stop on the tour is San Giovanni in Conca, Milan's last remaining Romanesque crypt, surreally hidden beneath the traffic-clogged Piazza Missori.

Personal shopper Melanie Payge

La Latteria, on Via San Marco, is equally overlooked by guidebooks. Old milk stores of its kind are dying out, but the blue-tiled, eight-table joint—covered in pictures of flowers—overflows. “Congratulations," booms a regular as you take your seat. “You've found Milan's last authentic restaurant!" You try the signature Crudaiola All Arturo Con Burgul, an assortment of market-fresh vegetables with glugs of olive oil and bulgur wheat, and follow it up with ice cream and stewed apples. Given the no-reservations policy, newcomers rush your table as you exit.

As you approach the second hotel of your stay, the Bulgari, you are overtaken by brash supercars racing up its private lane. Beyond the hotel gates, though, you find verdant grounds adjoining the city's Orto Botanico and interiors of oak, bronze and matte black marble. Bulgari's first foray into the hotel field is a surprisingly calming space—not least its plush basement spa, where you enjoy an hour-long massage before dipping into the golden, mosaic-lined pool.

Italians are known for their ability to take it easy, and there's no better example of this impulse than the Duomo. The cathedral, characterized by a mish-mash of styles and influences, took nearly six centuries to complete (locals call it their “never-ending story"). On the roof, amid a forest of spires, you are treated to a view of Milan's equally eclectic skyline, dominated by the Modernist monolith the Pirelli Tower and the bulging, buttressed Torre Velasca, famous for taking Brutalist architecture to new heights.

You see pigeons dive-bombing shoppers as you enter the crucifix-shaped Galleria Vittorio Emanuele II, which opened in 1867 and is said to be the world's oldest mall. Campari was invented below the mall's glass-vaulted roof, so you order the carmine-colored beverage at Camparino in Galleria, which sets you up for a whirlwind perusal of the futurist art in Museo del Novocento, a quick totter across Piazza del Duomo.

Dinner is at the colorful Giacomo Arengario, located at the top of the museum's Guggenheim-like spiral ramp. You have seared tuna steak served with umami-rich asparagus parmigiano, which you munch while taking in an epic close-up view of the Duomo. Back outside, you are surprised to find yourself alone, gazing up at the astonishingly dense concentration of spires. Happy voices lure you back toward the terrace bars lining the shopping arcade. There's time for one more Campari before bed.

The elegant interior of La ScalaThe elegant interior of La Scala

DAY THREE | You wake on soft cotton sheets in your handsome suite, pad over to the spacious walk-in closet and pluck today's outfit from impressively heavy oak hangers. Suitably attired, you head to the Armani Hotel's Bamboo Bar, with its louvered windows looking over the city's rooftops and women in crisp white shirts downing espressos. Milan may be fashion-obsessed, but food still counts: You kick off your day with slices of robust Culatello di Zibello, the king of Italian cured hams, alongside artisanal rolls and a brut prosecco.

You have more style-watching in store today, much of it overseen by personal shopper Melanie Payge, whose clients have included the royal family of Monaco. You start your journey on chic Via Manzoni, passing a lady in precipitous heels walking four dogs. In two seconds flat, your guide identifies the brand of your sweater (Jil Sander) and then deconstructs a man sporting the classic Milanese look of navy blazer, beige pants and loafers: “Larusmiani," she says, referring to the oldest luxury tailor on the luxe Via Montenapoleone. “That's where they all go."

You enter Gianluca Saitto's Brera boutique to a flurry of baci. “He's the new Armani," whispers Melanie as you explore an array of medieval-style tunics and rock 'n' roll jackets. Roberto Musso's hand-painted Como-silk dresses and Massimo Izzo's baroque aquatic jewelry are just as exclusive. Izzo, a brooding Sicilian, fits a weighty, double-finger seahorse ring onto your hand, and it feels like long-lost treasure dredged from the ocean floor.

Federico Sangalli's Piazza San Babila atelier transports you to the age of haute couture. Here, rows of elderly seamstresses work on pedal-operated machines, using 1950s techniques to create handcrafted clothing for Milanese society ladies. “When I took over the family business, we had perfect technique but an old language," says Sangalli. Then he cuts the lights to demonstrate his latest sartorial innovation: a fiber-optic, glow-in-the-dark silk gown. “When I saw the fabric," he recalls dreamily, “I said, 'I must create a dress.'"

Shoppers in front of a Gucci store on Via MontenapoleoneShoppers in front of a Gucci store on Via Montenapoleone

Your next stop is Melanie's favorite lunch spot, Il Salumaio di Montenapoleone, which occupies the Bagatti Valsecchi Museum's neo-Renaissance courtyard. Gilded youths swap gossip over homemade pasta—for which the restaurant and delicatessen justifiably are famed—while the owner smokes a fat cigar on the sidelines. Transfixed, you consume a generous plate of spinach and ricotta tortellini with butter and sage. Like the venue's supermodel clientele, it's beautifully sleek and light.

You continue your immersion in the good life at Villa Necchi Campiglio, a 1930s residence designed by Piero Portaluppi that now serves as a shrine to the decorative arts. You wander through a series of sublime rooms bedecked in walnut parquet, rosewood and lapis lazuli, their progressive Art Deco lines softened by 19th-century interiors. There is something dreamlike about the place, and you drift around blissfully unaware that you're running short on time for your last stop of the night.

It seems fitting that you'd end your stay in Milan at the iconic Teatro alla Scala—La Scala—the spiritual home of opera, Italy's defining art. The exquisite neoclassical theater opened in 1778 with a performance by Antonio Salieri. Tonight, you'll be seeing “Così fan tutte" by Mozart, the composer who drove Salieri into a downward spiral of pathological jealousy.

The Palazzo Parigi hotel, which occupies a 17th-century palaceThe Palazzo Parigi hotel, which occupies a 17th-century palace

There's little time for dinner before the show, but the Italians have elevated the aperitivo into a compelling substitute—not least at the Bulgari. You sip the hotel's gin- and Aperol-laced namesake cocktail at a secluded garden table, while demolishing a tray of salty focaccia, rich almonds, golfball-size mozzarella bocconcini and prosciutto piadine. That's the body taken care of—now for the soul.

Upon entering La Scala, Stendhal is said to have succumbed to the syndrome named for him—the lavish gilt-and-crimson décor overwhelming his emotions so thoroughly he had a breakdown. While you don't swoon with appreciation at the sight of the theater, it is impressive, more so when the music swirls around the room. Soon, though, you find your attention flitting between the lovers on stage and the mise-en-scène of Milanese socialites at play, unsure which is the more compelling.

Keyed up by the opera and the sudden roar of scooters radiating from La Scala's steps, you walk a hundred yards to the still-lit Galleria Vittorio Emanuele II. You're intending to make a final sweep of its elegant naves (and maybe satisfy your newfound Campari itch) but instead stop at the entrance, distracted by two workmen buffing its façade. The curtain has fallen at La Scala, but Milan is already prepping for tomorrow's show.

Antwerp-based writer Clodagh Kinsella has decided to rethink her wardrobe since returning from Milan.

This article was written by Clodagh Kinsella from Rhapsody Magazine and was legally licensed through the NewsCred publisher network.