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I went into my first trip to Milan with the same unbridled anticipation as a kid on Christmas morning or a super-fan meeting their celebrity crush. For any fashion lover, the Italian city holds a certain otherworldly mysticism—it hosts the most coveted runways, attracts international A-list crowds and has some of the world’s best shopping. For the clothing-obsessed, it’s like stepping into a fairytale. Indeed, the first thing I noticed on the modish Milanese streets is that it’s impossible to be overdressed, and it’s even harder to be unsatisfied. Everyone is inexplicably good-looking, the food is amazing and sartorial history is tucked in every cobblestoned corner. I soon discovered that Milan is more than just a shopping haven. It’s also a hub of innovative wellness, avant-garde art and architectural awe. Like its fashion, Milan itself transcends trends. A city rich with ancient history and cultural newness, it seamlessly weaves together centuries-old wonder with cutting-edge modernism. This is why, if you are planning a trip to the style capital, arming yourself with a Milan itinerary is key. You will, of course, be shopping a lot, so packing is a strategic affair. Before leaving, I picked up the vegan leather Metro backpack and packing cubes from Canadian brand Monos, which were a lifesaver when it came to conserving space and using optimal storage. And while planning is important, be sure to leave time to meander—you’ll discover some amazing people-watching by wandering over to the Brera neighbourhood and Sempione Park. Below, the editor-approved Milan travel guide for fashion lovers.
Where to stay in Milan: Portrait Hotel Milano
Photography courtesy of Portrait Milano
If you’re looking to experience equal parts history, fashion and luxury hospitality, this Milanese institution is a bucket-list item. Built in the 16th century as a seminary, the Portrait Milano is a majestic landmark at the heart of the city’s fashion district, Corso Venezia, and a ten-minute walk from the iconic Gothic Duomo Cathedral.
Photography courtesy of Portrait Milano
Over the last decade, it was transformed by the Ferragamo family (yes, that Ferragamo) into one of the most opulent stays in the city. The baroque-inspired rooms offer a taste of old-world grandeur, while the property’s sprawling piazza and centuries-old columns centre guests in the marvels of the ancient seminary.
Photography courtesy of Portrait Milano
Not to be missed is the Longevity Spa, which merges biohacking tech and holistic wellness. Its restaurant, 10_11, is frequented by visitors from all over the city—beloved for its imposing architecture, lush garden and award-winning Italian dining. [cta affiliate=”cj” align=”center” format=”button” url=”https://www.lungarnocollection.com/portrait-milano-hotel/”]Learn More[/cta]
Where to shop in Milan: Via Montenapoleone & Bivio
Photo by Valentina Frugiuele/Getty Images
Think of Via Montenapoleone as New York City’s Fifth Avenue, but smaller, densely concentrated and even more luxe. Named the world’s most expensive street, the 350-meter strip is home to some of the world’s most exclusive flagships. Heritage Italian brands Versace and Loro Piana have stores here, alongside buzzy boutiques like Bottega Veneta. A bonus for designer fanatics: it’s just steps away from the must-see Armani Hotel. [instagram-oembed url=”https://www.instagram.com/p/DKYviUuoHfc/?hl=en&img_index=1″ /] Additionally, a visit to Milan would not be complete without a taste of its world-renowned vintage shopping. Bivio is a beloved local hallmark of second-hand fashion, with multiple locations across the city. From vintage Prada heels to retro Pucci jeans, it boasts a sea of hard-to-find designer gems at gloriously marked-down prices. Pro tip: If your trip lands on a Sunday, head to the Navigli neighbourhood for the weekly flea market—tents line the picturesque canal with home decor, vintage clothing and art.
Where to relax in Milan: De Montel Terme Milano
Photography courtesy of De Montel
Once an abandoned horse stable, De Montel was reopened in April 2025 as the largest thermal spa in Italy. While thermal pools are an ancient practice for relieving stress, soothing skin and promoting circulation, each pool at De Montel—which is powered by solar panels and uses repurposed rainwater—is uniquely beneficial and innovative.
Photography courtesy of De Montel
The salt pool has a zero-gravity experience, allowing you to experience weightlessness as you float atop the water’s surface. The indoor “blade” pool, conversely, is a concentrated flow of water that massages the face and body to promote lymphatic drainage, circulation and tension release. There is also an array of saunas, whirlpools and plunge pools, as well as a restaurant and bar for all-day relaxation. Passes start at three hours, giving you ample time to explore the grounds, which just so happen to be shaped as a horseshoe. [cta affiliate=”cj” align=”center” format=”button” url=”https://www.demontel.it/en/”]Learn More[/cta]
Where to have an aperitif in Milan: Bar Basso
[instagram-oembed url=”https://www.instagram.com/p/CYdqNXDsFXW/?img_index=1″ /] Remember the Negroni Sbagliato? Bar Basso invented it. Known as the Negroni’s accidental cousin, the now-viral cocktail was born here in 1972, when the establishment had run out of gin and bartender Mirko Stocchetto used prosecco instead. If you’re into mixology lore or simply want a well-made drink, stop into Bar Basso for a taste of history. Bar Basso was one of the first bars in Milan to adopt the aperitif, the Italian cultural tradition of eating a small meal before dinner to stimulate the appetite. As such, it also serves up delicious pairing nibbles, from buttery focaccia to garlicky olives. [cta affiliate=”cj” align=”center” format=”button” url=”http://barbasso.com/en/”]Learn More[/cta]
Where to learn in Milan: Fondazione Prada
[instagram-oembed url=”https://www.instagram.com/p/C9ZalVhOCWH/?hl=en&img_index=1″ /] While there are many enriching museums in Milan, this is the ultimate visit for Miuccia Prada fans. Both an architectural attraction and a piece of fashion history, Fondazione Prada is an extension of Ms. Prada’s design philosophy: that art and learning are foundational to navigating the world.
Photo by Attilio Maranzano, via Fondazione Prada
Inside the museum are all sorts of exhibitions—from archaeological displays and art installations to dance performances and star-studded movie screenings. (Yorgos Lanthimos’s Poor Things premiered there in 2024.) To caffeinate, step into Bar Luce, a colourful café designed by famed director Wes Anderson. If you’re visiting in the evening, the rooftop Torre bar is not to be missed. [cta affiliate=”cj” align=”center” format=”button” url=”https://www.fondazioneprada.org/visit/visit-milan/?lang=en”]Learn More[/cta]
Where to eat in Milan: Ristorante La Brisa
[instagram-oembed url=”https://www.instagram.com/p/CiPN2evN-pj/?img_index=1″ /] Located in front of ancient Roman ruins that were once an imperial palace, this restaurant, led by chef Antonio Facciolo, has become a local dining favourite over the years. Tucked away in the heart of the city, the quaint space spans from a veranda to a shaded garden, cocooning guests in a nature-filled oasis and romantic candle-lit dining. The food, which puts a modern spin on traditional Italian cuisine, is also a singular experience. A monthly-rotating menu pulls inspiration from fresh seasonal ingredients, with fish, meat and vegetarian options available—as well as exceptional wine pairings. [cta affiliate=”cj” align=”center” format=”button” url=”https://www.ristorantelabrisa.it/en/”]Learn More[/cta] Continue Reading
