Milan Mastered: An Insider’s Guide to Italy’s Capital of Cool

With captivating contrasts of vintage grandeur and gritty glamour, Milan has a way of seducing visitors in every season.

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Milan may be Italy's economic engine, but this city runs on an intoxicating fuel of spritz, style and sheer creativity. The undisputed capital of cool seamlessly blends centuries of heritage with a cutting-edge verve that makes it utterly inimitable. With captivating contrasts of vintage grandeur and gritty glamour, Milan has a way of seducing visitors in every season.

But come spring, when the entire town is engulfed in Salone del Mobile's creative crescendo, Milan reaches rapturous new heights. The world's premier furniture fair transforms the city into an unparalleled design mecca; this year it takes place from April 16 to April 21. The main event takes over the sprawling Rho Fiera fairgrounds, while Fuorisalone turns Milan into a citywide gallery with brands, studios and more installing mind-bending displays in unexpected spaces. Recent years have seen visionary collaborations with talents like Formafantasma, Hélène Binet and even David Lynch.

For the ever forward-thinking Milan—a place of big ideas, major investment and rapid innovation busily sprouting new subway lines, cutting-edge hotels and infrastructure for the 2026 Winter Olympics—hosting Salone is simply second nature. After all, creative devotion courses through this city's veins year-round. The home of Prada, Campari and da Vinci’s The Last Supper knows a thing or two about splashy reinvention. And let's not forget about Milan Fashion Week, every February and September.

Once one of Italy's most underrated gems, Milan now draws visitors from all over Europe and around the world with its globally renowned fashion pedigree and artistic quarters brimming with bohemian bravura. Whether your religion is retail worship or the hallowed rites of aperitivo hour, this once-overlooked city has truly blossomed into La Capitale del Cool. Forget skipping Milan—you'll want to go the distance to soak up every last spritz of its stylish spirit.

Where to Stay

Portrait Milano

  • Corso Venezia, 11, 20121 Milan, Italy

Move over, corporate Milan—this baroque bombshell is the the Italian fashion capital's newest hit. Portrait Milano struts its stuff in the heart of the Quadrilatero della Moda (Fashion District), having traded its former convent life for a glamorous reinvention. Beyond the courtyard-turned-public-piazza awaits utter indulgence—from the brand-spankin’ new Longevity Spa with its stunning vaulted swimming pool to fashion boutiques and wine-paired bliss at the restaurant. But the real showstoppers? The sumptuous suites dripping in velvet, walnut and custom leather details.

Portrait Milano room. Portrait Milano

Bulgari Hotel Milano

  • Via Privata Fratelli Gabba, 7B, 20121 Milan, Italy

The Bulgari, which already boasts a luxury hotel in Rome, seduces Milan's most stylish set with lush garden revelry and impeccable Italian hospitality. Sip spritzy aperitivi under shady horse chestnuts before retreating to rooms adorned in sleek marble, bronze and rich woods. The spa's gilded mosaic pool practically demands a dip, while the restaurant wows with chef Niko Romito's classic fare. Whether lounging al fresco or cocooned in Bulgari's polished environs, you'll feel utterly invigorated—and utterly glamorous—at this oasis of la dolce vita.

Bulgari Hotel Milano. tommypicone

Vico Milano

  • Corso Genova, 11, 20123 Milan, Italy

Looking for the hottest under-the-radar address in Milan? Then keep Vico Milano's fashionable digs to yourself. This seven-room jewel box, dreamed up by boutique hotel savant Neri Baccheschi Berti, seamlessly fuses global influences into an eclectic, art-filled haven. Every detail delights, from the Moroccan-tiled bathrooms and antique Greek marble to the rotating gallery installations. Cuddle up in the library or sip craft cocktails at the spiffy local artisan bar—just don't reveal this hidden gem's whereabouts. It's our little secret.

Vico Milano entrance. Matteo Serpi

Casa Cipriani Milano

  • Via Palestro, 24, 20121 Milan, Italy

Consider this your VIP pass to elegant Italian living, Cipriani-style. The hospitality heavyweights have created Milan's premier members-only urban palazzo, oozing cultivated luxe at every turn. The vibe marries serene pied-à-terre and grand residenza in just 15 sumptuous Michele Bonan-designed rooms that scream yacht club chic. Linger over bellinis and cicchetti at the polished wood-paneled bar before heading to the pampering spa. Don’t forget to pack a jacket for dinner, where you'll truly feel like Milanese aristocracy.

Casa Cipriani Milano Signature Suite. Casa Cipriani

What to Do:

Museo Cenacolo Vinciano (The Last Supper Museum)

  • Piazza di Santa Maria delle Grazie, 2, 20123 Milan, Italy (inside the refectory of the Convent of Santa Maria delle Grazie)

Step into the holy grail of Renaissance art—the refectory housing Leonardo da Vinci's legendary Last Supper. This jaw-dropping 15th-century mural captures Jesus' dramatic betrayal revelation with innovative mastery. But don't linger too long; visits are capped at 15 minutes to preserve the delicate fresco. Book well in advance to secure your audience with this iconic masterpiece.

A view of Leonardo da Vinci's The Last Supper. Getty Images

Milan's Canals

Once Milan's vital arteries for trade, today, these tamed 12th-century waterways (navigli) offer a delightful detour from the city's hustle. Meander along the Naviglio Grande and Pavese, the last remnants, and embrace the lively al fresco culture of cafes, restaurants and shops lining the banks. Come summertime, the whole district thrums with aperitivo fever.

Milan's Canals. Laurine Peyrard on Unsplash

Brera District

Eclectic Brera oozes an irresistible bohemian vibe. This artistic enclave seduces with cobblestone charm, antique haunts, too-cool-for-school boutiques and galleries galore. Don't miss the works of art at the masterpiece-laden Pinacoteca di Brera (Brera Art Gallery) and the lush Botanical Garden hideaway. Fuel up at trattorias or buzzy bars—Brera's creative spirit is utterly contagious. 

Brera Academy of Fine Arts, Brera district. Eddy Buttarelli/REDA&CO/Universal Images Group via Getty Images

Fondazione Prada

  • Largo Isarco, 2, 20139 Milan, Italy

Forget traditional art museums—Fondazione Prada rewrites the rules. This former gin distillery now houses mind-bending contemporary art exhibitions curated by style maven Miuccia Prada herself. The avant-garde complex masterfully blends renovated buildings with starchitect Rem Koolhaas' bold new additions, like the striking gold-tiled "Haunted House." Embracing the unconventional is a given here.

View of the Cinema area during the inauguration of "Multiple Canvases" at Fondazione Prada. Rosdiana Ciaravolo/Getty Images

Where to Shop:

10 Corso Como

  • Corso Como, 10, 20154 Milan, Italy

Where art, fashion, food and life itself converge into one dazzling mosaic—that's the manifesto of 10 Corso Como. Founder Carla Sozzani's living gallery/restaurant/boutique hotel blends cultural curiosities into a tantalizing immersive experience. Wander from covetable Italian designs to photography exhibits, then linger over aperitivo on the verdant courtyard patio. It's Milan's most marvelous micro-cosmos.

10 Corso Como. WireImage

Raw&Co

  • Corso Magenta, 10, 20123 Milan, Italy

Hidden between Milanese historic buildings, Raw&Co is an ever-evolving concept store that resembles an eclectic apartment spread across multiple floors. Each room tells a different story through a thoughtfully curated melange of vintage, modern and handcrafted pieces from around the globe. With decor inspirations rotating seasonally, every visit to this house of treasures is more compelling than the last.

Pettinaroli

  • Via Brera, 4, 20121 Milan, Italy

Step into Pettinaroli and be transported to a bygone era of Italian artisanship. This 1881 stationery-turned-printing house has mastered exquisite craftsmanship for over a century. Whether it's leather-bound albums, letterpress wedding invites or antique maps adorning the shelves, every piece exudes timeless elegance. Pettinaroli redefines what it means to put pen to paper.

Pettinaroli. Pettinaroli

Nilufar Depot

  • Viale Vincenzo Lancetti, 34, 20158 Milan, Italy

For interiors aficionados, Nilufar Depot is the ultimate objet d'art playground. Nina Yashar's legendary design warehouse takes "more is more" to sublime heights. This three-story stunner channels La Scala's dramatic ambiance with vintage Italian furnishings dramatically staged across balconied walkways. Even window shopping feels like wandering through a curated design museum.

Where to Eat:

Signor Lievito

  • Via Panfilo Castaldi, 26, 20124 Milan, Italy

Bread is the star at Signor Lievito, where model-turned-baker Natalia Nikitina works magic with a 120-year-old mother yeast. Before it even opened, carb connoisseurs were buzzing about the boulangerie's obscenely flavorful baguettes, bulkas and Apulian focaccias. Who knew bread could be this seductive?

Signor Lievito. Signor Lievito

Langosteria Cucina

  • Via Savona, 10, 20144 Milan, Italy

Like being invited to an intimate dinner party at a well-traveled friend's home—that's the vibe at Langosteria Cucina. Designed by Dimorestudio, the cozy 40-seater eschews industrial kitchens for a plush, lived-in aesthetic blending ‘70s moodiness with Japanese restraint. Tuck into the day's freshest catch or try classic risotto while surrounded by collected treasures from the owners' global jaunts. Don't forget to end with an order of gelato.

Langosteria Cucina. TOMMYILAI

Bar Luce

  • Largo Isarco, 2, 20139 Milan, Italy (inside Fondazione Prada)

Step through Wes Anderson's whimsical time portal recreating 1950s and ’60s Milan at this ode to mid-century Italian cinema. Retro formica chairs, jukeboxes, pinball machines and terrazzo floors channel classic films like Rocco and His Brothers. The wallpaper's Galleria Vittorio Emanuele flourishes make you feel you've shrunk down to miniature—in the most delightfully Anderson-esque way.

Bar Luce. Bar Luce

Nebbia

  • Via Evangelista Torricelli, 15, 20136 Milan, Italy

Milan's neo-trattoria trend finds a standout in canal-side charmer Nebbia. The seasonal menu spotlights elevated Lombardian comfort fare like duck liver brioche and octopus with pork cheek, best washed down with a natural wine from the tightly curated list. With its rich flavors, forward-thinking twists and unfussy vibe, it embodies the future of Italian dining.

Where to Drink:

Terrazza Aperol

  • Piazza del Duomo, 20121 Milan, Italy

When Milan sheds its winter coat, it's time to party al fresco at the one and only Terrazza Aperol. This piazza-side aperitivo hotspot is the ultimate ostentatious orange homage to Italy's beloved pre-dinner tipple. Designer Antonio Piciulo captured the cocktail's effervescent essence with vibrant hues and an unbeatable duomo-facing terrace. Sunset spritzes pair perfectly with crunchy chips and mouthwatering cicchetti for the ultimate afternoon affair.

Terrazza Aperol. Terrazza Aperol

Bar Basso

  • Via Plinio, 39, 20129 Milan, Italy

Behind gilded doors, Maurizio Stocchetto’s Bar Basso's is like being transported back in time. This dimly-lit, mirror-lined cicchetteria is a bonafide mid-century nightlife time capsule where aperitivo culture was born—quite literally, as the Negroni Sbagliato was invented here by happy accident. Sip the frothy original from a vintage Venetian goblet alongside a cross-section of old-school Milanese; from fashionistas to neighborhood regulars, all roads lead to this hallowed haunt.

Bar Basso. Bar Basso

Camparino in Galleria

  • Galleria Vittorio Emanuele II, 20121 Milan, Italy

They don't come much more quintessentially Milanese than this 1915 Galleria bar, the birthplace of the iconic Campari. With its original mosaics, frescoes and soaring ceilings, Camparino epitomizes Italian aperitivo grandeur. It's the perfect elegant pit stop for locals and culture vultures fresh from the Teatro alla Scala opera house or an exhibition at the Palazzo.

Camparino in Galleria. Camparino

Bar Nico

  • Via Lecco, 11, 20124 Milan, Italy

Old-world wine bar meets new European chic at Bar Nico, already crowned one of Milan's trendiest indirizzi. The Studio Sagoma-designed interiors subtly nod to the site's history as a tire shop and pasta factory, while championing their rigorously pared-back, environmentally-conscious aesthetic. Sink into sculptural seating savoring the thoughtfully curated natural wine list amidst an atmosphere that could be plucked from Paris, Madrid, New York or London—yet unmistakably maintains its Milanese soul.

Bar Nico. Alessandro Saletta

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