Milan, the capital of “Italian chic”, where high fashion meets centuries-old architecture and every street hums with quiet sophistication. It’s a city I’ve long wanted to experience, and from the moment I arrived, it felt like stepping into a perfectly curated wardrobe—polished, precise, and full of unexpected details.
Day 1
Morning:
Quadrilatero della moda
My Milanese adventure began in the heart of the Quadrilatero della moda, Milan’s prestigious fashion district, where luxury radiates from every cobbled street. I checked in at Portrait Milano, a serene oasis tucked within a grand 16th-century courtyard. It’s effortlessly elegant, with impeccable design and the kind of calm you rarely find in a fashion capital. Just outside the doors: a wonderland of designer boutiques—Prada, Versace, Gucci, and a few independent gems that made me stop in my tracks.
Designer Shopping at Galleria Vittorio Emanuele II & Rinascente
Leaving the fashion district, I headed towards Galleria Vittorio Emanuele II, Milan’s famed 19th-century shopping arcade. Beneath its soaring glass dome and intricate mosaics, the atmosphere feels more like a royal gallery than a mall. I found my new favourite suitcase at Bric’s, tucked amongst the glittering storefronts.
Connected to the Galleria is Rinascente, Milan’s legendary department store. It spans multiple floors, offering everything from contemporary Italian fashion to niche beauty finds. But the true highlight? The rooftop terrace with a sweeping view of the Duomo di Milano—a perfect spot to pause, photograph, and take it all in.
Afternoon:
Exploring the Duomo di Milano
The Duomo is, without a doubt, the heart of Milan. This Gothic marvel, nearly 600 years in the making, is breathtaking up close. Every spire, statue, and stone seems to whisper a secret from the past. I took the lift up to the Rooftop Terrace, where panoramic views of the city stretch endlessly across the skyline. (Tip: It could be worth booking the rooftop tickets in advance to avoid the queues. )
Afterwards, I wandered through Piazza del Duomo, letting the energy of the city soak in. Street performers, polished locals, and that unmistakable Milanese buzz—it all felt alive. If you fancy more exploring, continue on to Fontana San Babila and stroll down Corso Venezia, where hidden boutiques and beautiful buildings line the route.
Evening:
Pinacoteca di Brera
Back at the hotel to drop off shopping bags (plural!), I made my way to Pinacoteca di Brera – home to a stunning collection of Italian Renaissance works, including pieces by Caravaggio. This museum quickly became the cultural highlight of my trip. It’s intimate, immersive, and beautifully curated.
Note: The first time I went, tickets had sold out. Definitely book online ahead of time. Also, the entrance is up a flight of stairs from the main courtyard, which isn’t obvious at first glance.
The Manzoni
Dinner that evening was at The Manzoni, a concept restaurant and showroom designed by the British designer Tom Dixon. The interiors are moody, sculptural, and oh-so-Milan. The food? Fresh, modern, and beautifully plated—though portions are on the smaller side, so I recommend ordering a few dishes to share.
Day Two
Morning:
Villa Invernizzi
The next morning began with something completely unexpected—flamingos. Yes, flamingos in Milan. On Via Cappuccini, just steps from my hotel, sits Villa Invernizzi—a private residence with an enclosed garden where these pink birds roam gracefully. While the villa isn’t open to the public, peering through the wrought-iron gates felt like discovering a hidden pocket of whimsy in the middle of the city.
QC Termemilano
From there, I headed to QC Termemilano, a luxurious thermal spa set in a converted 19th-century tram depot. Think steamy outdoor pools, Himalayan salt rooms, bubbling hydrotherapy baths, and cocoon-like loungers for napping. After yesterday’s hustle, this was pure bliss. Tip: It would be worth arriving early if you want the pool to yourself 🙂 .
Afternoon:
Castello Sforzesco and Parco Sempione
Revived and rejuvenated, I made my way to Castello Sforzesco, a striking medieval fortress with expansive courtyards and a cluster of museums within its walls. Even if you skip the interior exhibitions, simply walking through the grounds offers a sense of Milan’s layered history.
Behind the castle lies Parco Sempione, a sprawling park ideal for a peaceful stroll. Locals picnic beneath shady trees and joggers wind their way along the paths. At the edge stands Arco della Pace, Milan’s neoclassical triumphal arch, gleaming in the afternoon light.
Evening:
Dinner and Teatro alla Scala
Dinner came with a side of shopping at Eataly Milano Smeraldo, a multi-storey temple of Italian gastronomy. Fresh pasta, regional cheeses, and gourmet sauces – if it could fit in my suitcase, it was coming! Note: Eataly has stores worldwide – check if your hometown has one before you overpack like I did.
If you still have energy, nearby Teatro alla Scala awaits. Whether it’s a performance or a guided tour, this legendary opera house is a must for culture lovers. It’s elegant, opulent, and very Milan.
If you’re up for one last architectural marvel, you can head to Piazza Gae Aulenti to see Bosco Verticale – a pair of futuris tic residential towers draped in cascading greenery. It’s like nature and modernism had a beautifully curated baby!
Final Reflections:
Now, as I sip tea at Ten Eleven—the courtyard restaurant at Portrait Milano—I feel deeply content. Milan surprised me. It’s not a city that shouts for attention. It draws you in quietly, with elegant streets, impeccable style, and moments of beauty that stay with you long after you leave.
From the runway-ready fashion finds and Renaissance masterpieces to serene spas and secret flamingos, every moment felt curated just for me. The city has a rhythm all its own—modern yet timeless, bold yet refined.
If you’re planning a visit, I hope my two-day Milan itinerary gives you the perfect mix of inspiration and insight. It’s a city that deserves to be experienced slowly, thoughtfully, and in style.
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