5 Days in Milan: The Ultimate Art, Culture & Fashion Itinerary for Families with Tweens

After dropping your bags at the hotel, spend your first afternoon in the heart of Milan: explore the area around the Duomo di Milano and the grand arcade of the Galleria Vittorio Emanuele II. The towering Gothic cathedral and the glass-roofed gallery offer “wow” moments that appeal to all ages.

For tweens, encourage a photo scavenger hunt in the Galleria—find the bull mosaic, spot the luxury window displays, and capture a selfie on the steps of the Duomo. Then head into the nearby gallery of Museo del Novecento, where the bright, modern art is accessible and fun for tweens.

Later on, stroll through the artsy district of Brera, where cobblestoned lanes, boutique shops, and café stops make it relaxed yet stylish. Settle in at Osteria di Brera, a charming trattoria that blends Milanese tradition with modern flair.

Afterward, treat everyone to gelato at Gelateria Rivareno Brera and enjoy an evening stroll through the district’s glowing galleries and boutiques.

Insider tip: Book advance tickets to explore the Duomo rooftop—it offers a truly unique perspective of Milan’s history and skyline from above.

Today is all about style. Begin with the renowned shopping street Via Monte Napoleone in the Quadrilatero della Moda—the glow of designer windows, street-style spotting, and plenty of “look at that!” inspiration. This is Milan at its most elegant: where fashion, architecture, and people-watching blend into one living runway.

For a deeper dive, set out on the Milan Couture Fashion Tour—a guided walk that takes you behind the scenes of Italian design, iconic brands, and the city’s enduring connection to the fashion world. It’s the perfect way for tweens (and adults) to understand how style and craftsmanship are woven into Milan’s identity.

In the afternoon, keep it light and creative with a visit to Armani/Silos, Giorgio Armani’s museum and concept space celebrating 40 years of fashion through beautifully curated exhibits. It’s an inspiring stop for budding designers and art lovers alike.

When evening arrives, enjoy dinner at Ristorante Bice, a beloved Milan institution near the fashion district that’s long been a favorite among designers and locals alike. Its chic yet welcoming atmosphere and classic Tuscan-Milanese dishes—like risotto alla milanese or handmade pasta—make it the perfect end to a stylish day. For dessert, stroll to CioccolatItaliani, where molten chocolate and gelato creations are as fashionable as their presentation.

Insider tip: Let each kid pick one accessory or souvenir that speaks to their own style — something they’ll wear or use back home to remember their Milan moment.

Dedicate this day to smart shopping beyond the city center. Start with Scalo Milano Outlet & More, just 15 minutes from downtown by free shuttle, offering over 180 boutiques spanning fashion, design, and gourmet delights.

For a more elevated experience, venture to Fidenza Village—part of The Bicester Collection—about an hour from Milan. Here, you can enjoy The Apartment, an elegant private suite where personal stylists curate looks from top Italian and international brands while you sip prosecco and unwind. It’s Milan’s most luxurious outlet experience and ideal for families who appreciate comfort and curated service.

Alternatively, those seeking a classic designer-hunting adventure can visit Serravalle Designer Outlet, Europe’s largest luxury outlet, with over 230 boutiques featuring Prada, Gucci, and Ferragamo.

After a full day of shopping, unwind back at Magna Pars L’Hotel à Parfum and enjoy dinner at DA NOI IN, where each dish is inspired by fragrance notes—the perfect, relaxing end to your stylish Milan day.

Insider tip: Reserve your shuttles and Apartment experience in advance to ensure availability.

You can’t leave Italy without savoring its food—and Milan’s cuisine is as refined as its fashion. Begin late morning with the Essentials of Milan Food Tour, a three-hour stroll through the historic center led by a local food expert. Between espresso tastings, gourmet panini, artisanal cheeses, and an introduction to the city’s beloved aperitivo culture, you’ll discover how Milan’s flavors reflect its stylish spirit.

In the afternoon, trade tasting for tailoring at a fashion workshop in a Milan atelier, where the master tailor and educator invites guests into the world of bespoke Italian craftsmanship. Learn the fundamentals of couture—from fabric selection to hand stitching—and gain a new appreciation for the artistry behind the pieces that define Milan’s runways.

For your final evening, enjoy a true Milanese classic: risotto con ossobuco at Trattoria del Nuovo Macello. This beloved neighborhood restaurant has been serving authentic Milanese comfort food for generations, balancing tradition with warmth. It’s a fitting finale—comforting, local, and deeply rooted in the city’s culinary identity.

After dinner, take one final evening stroll and stop for gelato at Pavé–Gelati & Granite, a local favorite known for its creative seasonal flavors and small-batch craftsmanship.

Insider tip: Don’t miss the house specialty—risotto alla milanese with ossobuco—slow-cooked to perfection and brightened with saffron. Pair it with a glass of Lombard Nebbiolo for a true Milanese finale.