When you think of Milan, the first images that come to mind are usually the majestic Duomo, the elegant Galleria Vittorio Emanuele II, and the glossy windows of Via Montenapoleone. But if you scratch the surface, you’ll find a city rich in unexpected corners, quiet courtyards, and stories that blend design, history, and authenticity.
For travellers who crave depth, elegance, and a touch of surprise, discovering unusual things to do in Milan is a journey through layers of art, architecture, and innovation that few visitors ever experience.
The Hidden Cloisters of San Simpliciano
Milan’s charm often lies behind closed doors — literally. Just steps away from the lively Corso Garibaldi, the Cloisters of San Simpliciano offer a serene escape from the city’s energy. Built in the 15th century, this peaceful courtyard belongs to one of Milan’s oldest basilicas, and it’s still used by university students and local artists.
Why visit:
- It’s a perfect stop for those who appreciate architecture and tranquility.
- You can sit under the arcades, enjoy a quiet espresso, and admire centuries-old brickwork and climbing ivy.
- Few tourists know about it — making it a genuine hidden gem.
If you’re exploring unusual things to do in Milan, this cloister offers a moment of calm that balances the city’s buzz — ideal for travellers seeking beauty without the crowds.
The Vertical Forest: Nature Meets Design
Milan isn’t just fashion — it’s forward-thinking design, sustainability, and innovation. The Bosco Verticale, or Vertical Forest, is a striking example. Two residential towers completely covered in over 900 trees and 20,000 plants rise above the Porta Nuova district, redefining the idea of urban living.
Why visit:
- You’ll witness one of the world’s most awarded examples of sustainable architecture.
- The nearby pedestrian area, Piazza Gae Aulenti, is ideal for a stroll, with cafés, concept stores, and green spaces where you can relax.
- At sunset, the reflections of the buildings create one of the most photogenic scenes in Milan.
For design lovers, it’s one of the unusual things to do in Milan that merges art, innovation, and environmental consciousness — a vision of the city’s future.
The Museum You Can Smell: MUBA – Museo dei Bambini
While Milan boasts many grand museums, the MUBA (Children’s Museum) inside the Rotonda della Besana offers something refreshingly different. Even if you’re travelling without kids, the space itself — a former baroque cemetery turned into a cultural centre — is worth a visit.
Why it’s special:
- Exhibitions engage all five senses, making it a playful yet artistic stop.
- The architecture of the Rotonda is stunning: a circular cloister surrounded by peaceful gardens.
- It’s rarely crowded, providing a quiet, local feel.
It’s the kind of discovery that redefines what a museum visit can be — and precisely the kind of experience that characterises the best unusual things to do in Milan.
Street Art and Artisan Workshops in Isola
If you’re drawn to authenticity and creativity, the Isola district is where Milan’s bohemian soul thrives. Once a working-class area, today it’s a hub of murals, design ateliers, and small wine bars that preserve a strong local identity.
What to do:
- Wander around Via Thaon di Revel and Via Carmagnola to admire colourful street art.
- Visit independent galleries or artisan studios — many artists are happy to chat about their work.
- Stop by a neighbourhood trattoria for an aperitivo with locals rather than tourists.
Isola’s mix of tradition and innovation embodies the spirit of modern Milan. Adding it to your itinerary ensures your list of unusual things to do in Milan includes a taste of the city’s real life — far from postcard clichés.
The Secret Rooftop Adventure: Castle’s Rooftop Panoramic Walk
Now for Milan’s best-kept secret — one even many locals haven’t experienced. Hidden inside the majestic Castello Sforzesco, a special guided route lets you climb up to the ramparts and walk along the rooftop paths.
Don’t miss out on Milan's ultimate secret! Experience the jaw-dropping Castle’s Rooftop Panoramic Walk where history and stunning views collide. Witness Sforza Castle and the dazzling cityscape like never before — a once-in-a-lifetime adventure that blends medieval architecture with breathtaking panoramas.
Why it’s unforgettable:
- You’ll enjoy a 360° view of the castle’s courtyards and Milan’s skyline, from the Duomo’s spires to modern skyscrapers.
- The tour is available only through selected cultural organisations (like Ad Artem) — making it truly exclusive.
- It’s the perfect photo opportunity, but also a moment of connection with Milan’s layered history.
For travellers looking for unusual things to do in Milan, this experience is a masterpiece of storytelling, design, and emotion — the kind of hidden treasure that transforms a good trip into an extraordinary one.
The Waterways of the Past: Navigli by Dusk
Even though the Navigli area is well-known, there’s a more poetic way to enjoy it: skip the busy aperitivo hour and explore it at dusk, when the lights reflect softly on the canals.
Insider’s tip:
- Visit the Vicolo dei Lavandai, an ancient stone washing area along the Naviglio Grande — a slice of 19th-century life that most tourists overlook.
- Take a guided boat tour to discover how Leonardo da Vinci engineered this system of canals that once connected Milan to the lakes.
- Choose a slow-food restaurant that uses local ingredients for dinner — it’s a perfect way to close your day.
Rediscovering Navigli through its quieter, historical side makes it one of the most unusual things to do in Milan, revealing how water once shaped the city’s soul.
Hidden Churches with Astonishing Art
Milan’s spiritual heart isn’t limited to the Duomo. In fact, some of its most beautiful churches are small, discreet, and rich in masterpieces.
Don’t miss:
- San Maurizio al Monastero Maggiore, often called “the Sistine Chapel of Milan,” covered entirely in 16th-century frescoes.
- San Bernardino alle Ossa, famous for its macabre yet fascinating chapel lined with human bones — a truly unforgettable stop.
- Both are centrally located but often overlooked, even by repeat visitors.
If your list of unusual things to do in Milan includes something truly moving, these hidden sanctuaries will leave a lasting impression.
Design and Nature at Porta Venezia Gardens
For a blend of art, leisure, and Milanese elegance, take a walk through the Giardini Pubblici Indro Montanelli, near Porta Venezia. Between sculptures, fountains, and tree-lined paths, you’ll find the Natural History Museum — Italy’s oldest — with impressive dioramas and exhibits.
Why it’s worth your time:
- The park’s 18th-century design offers a rare combination of historical landscape and urban comfort.
- There are open-air cafés where you can sip a cappuccino surrounded by greenery.
- In spring and autumn, it’s a visual feast of colours — a green escape in the heart of the city.
This stop shows that even the simplest pleasures — a walk in a beautifully designed park — can count among the most unusual things to do in Milan when approached with curiosity and style.
An Aperitivo with a View
Before ending your Milan adventure, indulge in one of the city’s favourite rituals: the aperitivo. But skip the crowded hotspots and choose a rooftop bar instead — such as those atop the Rinascente or in the Porta Nuova skyline.
As the city glows below you, toast with a Negroni or a glass of Franciacorta — a local sparkling wine from Lombardy. It’s a fitting finale for travellers who seek authenticity, elegance, and something a little different.
In Summary
Exploring unusual things to do in Milan means embracing the city’s true personality — sophisticated yet approachable, steeped in history yet open to innovation. From hidden cloisters and green architecture to art-filled churches and rooftop walks above medieval towers, Milan rewards those who look beyond its postcard icons.
For discerning travellers, it’s not just about ticking landmarks off a list, but about collecting moments of wonder — the quiet hum of a cloister, the surprise of a modern forest in the sky, the thrill of standing atop the Sforza Castle at sunset.
Milan’s hidden treasures await. All you need to do is look beyond the obvious — and the city will reveal its extraordinary heart.
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Credits
San Simpliciano Cloister by
G.dallorto, Attribution, via Wikimedia Commons Vicolo dei Lavandai by
Samoano~commonswiki,
CC BY-SA 3.0, via Wikimedia Commons