Best 2 Days In Milan Travel Itinerary: Hidden Gems & Iconic Spots

Welcome to the best 2 days in Milan travel itinerary — the guide I wish someone had given me my first time in the city. After coming to Milan a handful of times, I finally put together the perfect way to spend 2 days here: a mix of iconic sights, local gems, incredible food, gorgeous architecture, and those effortlessly cool Milan moments that make you fall in love with the city.

Milan is urban, stylish, young, and full of life — but also deeply rooted in history, art, and design. It’s one of those places that keeps getting better the more you explore it. Think biking through lush parks, sipping espresso above Prada, wandering vintage markets along the canals, catching art installations that feel like movie sets, and ending your nights in chic neighborhoods buzzing with energy.

This 2 days in Milan travel itinerary is designed to help you experience all sides of Milan — the classics on Day 1 and the cooler, more local vibes on Day 2 — without feeling rushed. Whether it’s your first trip or your fifth, here’s exactly how to spend 2 unforgettable days in Milan.

Day 1: Iconic Milan — The Essentials

1. The Duomo di Milano

Start your day at the Duomo, the world’s largest Gothic cathedral and truly one of the most breathtaking buildings on the planet. It’s stunning from every angle — the details, the spires, the symmetry. You can book rooftop tickets here or simply wander inside. Honestly, the exterior alone is worth the stop.

2. Galleria Vittorio Emanuele II & Marchesi 1824

Just a few steps away is the Galleria Vittorio Emanuele II — the famous glass-domed shopping arcade. The architecture is so intricate it might make you emotional (you’re not alone).

Before you leave, stop at Marchesi 1824, the café above Prada. It has beautiful pastries and an even better view. And yes — don’t forget to spin on the bull’s balls in the mosaic floor for good luck. Tradition is tradition.

3. Bike to Sforza Castle → Parco Sempione → Arco della Pace

Rent a bike and make your way toward Sforza Castle, then continue through Parco Sempione — Milan’s biggest urban park. I rode through here multiple times on my last trip and it’s honestly so gorgeous. The ride ends iconically at Arco della Pace, Milan’s own triumphal arch. Riding a bike gives you a completely different perspective of the city compared to walking — and it’s so much fun.

4. Galleria d’Arte Moderna (GAM)

Next, head to GAM: the Galleria d’Arte Moderna. This museum focuses on 19th- and 20th-century Italian works and — best part — admission is free. The building itself is stunning, and it’s a great break from the busier tourist areas.

5. LùBar (for lunch, dinner, or espresso)

Right outside the museum is LùBar, a dreamy Sicilian-inspired restaurant. The space is beautiful, the vibe is perfect, and the food is always good. Whether you want a full meal, a drink, or just an espresso, it’s worth stopping by. Highly recommend the avocado toast.

Day 2: Vintage, Culture, Design & Nightlife

1. Navigli Vintage Markets + Canals

Start your morning in Navigli, which I compare to Williamsburg in NYC — artsy, cool, eclectic. On weekends, they have vintage flea markets along the canals where you can find everything from clothing to ceramics to vinyl.

2. SERENDEEPITY (A Must for Music Lovers)

If you love vinyl or underground music culture, go to SERENDEEPITY. My friend Nicola Mazzetti owns it — he’s a DJ and just an overall vibe. I met him at a wedding in Iceland, and he’s created the most inspiring shop with an amazing record collection. You’ll find something special here, guaranteed. Milan’s vintage shopping scene is chef’s kiss.

Other Vintage + Thrift Shops to Check Out

10 Corso Como
Cloister
Guendi
Bivio
Humana
Mercantino Milano
Milanicons
Bitossi Home
My Vintage Attire
SERENDEEPITY
Via Montenapoleone (a street similar to 5th ave in NYC)

3. Fondazione Prada

Next, head to Fondazione Prada, a contemporary art complex that’s constantly evolving. Some installations feel unfinished in a cool, conceptual way — it’s definitely an experience.

Don’t skip:

The mushroom installation
Bar Luce, the café designed by Wes Anderson (it’s literally like stepping inside a film)

I have a full video about the museum which you can watch here to decide if you think it’s worth going.

4. MOGO – Eat, Drink, Dance

If you love dancing like I do, check if MOGO has any events happening. It’s a stylish & chic restaurant, a hi-fi listening space, and sometimes a party spot. I went solo on Halloween and ended up running into friends from Polifonic Festival — people were so warm and welcoming, which was a tiny culture shock coming from the US. It’s such a fun, unexpected Milan experience.

5. Bosco Verticale

Swing by Bosco Verticale, Milan’s iconic plant-covered residential towers by Stefano Boeri. I biked past it one night at 3 am with someone I met at MOGO, so I don’t have much footage — but trust me, it’s a must-see in daylight or at sunset.

6. 10 Corso Como

Add 10 Corso Como to your list- a concept shop & restaurant.
Expect:

art gallery
bookshop
courtyard installation
fashion
fragrance
iconic photo moments

Such a good place for inspiration, gifts, and exploring design.

7. Via Montenapoleone + Armani Hotel

Stroll down Via Montenapoleone (Milan’s version of Fifth Avenue): luxury shopping, stunning storefronts, and the most stylish people-watching. Stop into the Armani Hotel for tiramisu — their lobby bar is so chic.

Where to stay

I stayed in Brera for a week this last trip and I would definitely stay here again. It’s so romantic and lively. The restaurants stay open late, the streets are buzzy, and the whole area has this warm, magnetic energy.