2-Day Milan Itinerary: Duomo, Navigli & The Best Gluten-Free Pizza

Day 1: Fully running on espresso and no sleep. Also, the day one parent went missing… SOS.

We stayed at this cute little B&B with the tiniest elevator I have ever been in. The owners were so sweet! I mostly booked it because they had a triple room, and I wanted a more authentic experience than a hotel for my first night in Italy.

We had lunch near the Duomo, and it was the best gluten free pizza I’ve ever had @barmercurio_milano (we went back the next day). I’d booked us a tour that included “skip the line” for The Last Supper painting, which I highly recommend, although I think our guide was having a rough day…

This is what I booked:

The Last Supper has been on my list ever since I was 18 in the Louvre, and for some reason, I thought it was there . A guard let me know that “it’s actually in a church in Spain”… meanwhile, in Italy…

We continued the walking tour that covered all the city highlights. We went to Castle Sforza (Castello Sforzesco) and I walked across my first drawbridge, it was really cool though the pictures don’t do it justice. It was built in the 14th century, and the history of this fortress is really interesting!

Near the end of the tour, Dad went missing for about an hour (without his phone) trying to find a restroom. Mom was in shambles. I was circling the castle trying to find him. It was dark and cold and pouring rain, one umbrella broke from the wind, and I was questioning all my life decisions at this point. It’s day one and I’d already lost one parent???

But all was well, and now it’s a funny story. (Though he will be getting an Apple Airtag to keep in his pocket for any and all future international trips. ) We had dessert for dinner and it was the best gelato of the trip @chocolatmilano.

Life lesson of the day: No matter how well you plan, not everything will go according to plan… but everything will eventually work out.

Day 2: Duomo & Terraces + Navigli District

Bed & breakfasts always sound like a good idea until you have to wake up and speak and Italian before having caffeine. 😂 I kid, sort of… But in all honesty, I am sad that I never took a picture of the cute little breakfast room at our B&B. The owners were so lovely and kind.

I’d booked us a skip-the-line tour of the Duomo and Terraces and it was everything. Highly recommend – our guide was amazing and I learned so much. I was in awe of the stained glass, but definitely don’t skip the Terraces/rooftop for amazing architecture and views of Milan.

This is what I booked:

We wandered through the Galleria Vittorio Emanuele II (it was Sunday and super crowded), snapped a photo with Leonardo Da Vinci (statue), and hopped on a vintage tram to the Navigli district of canals for dinner, which was fascinating. (Be prepared to turn down a lot of rose bouquets from peddlers.) It’s really nice to sit outside overlooking the canals for dinner, and you have no shortage of restaurant/cafe/drink options.

Also, the metro in Milan is super easy to use, just like London/Paris, and you can tap on and off with a contactless card to pay if you don’t want to stop at a ticket machine. The lowest fare is automatically applied, and this works for trams and buses too! Ubers are also easy though… especially on Day 1 of any and all trips….

✨ Want a Milan Trip Like This?

Whether you’re planning a few stylish days in Milan before a river cruise or a full Italian escape, I can help you create a seamless, stress-free itinerary—with luxury perks, personalized hotel and tour bookings, and expert support every step of the way.

📩 Click here to plan your trip with Styled Getaways

---

More from the Travel Diaries Series:

• Travel Diaries: Paris
• Travel Diaries: The Black Forest
• Travel Diaries: Switzerland & The Bernina Express!

---

Affiliate Link Disclaimer:

This post contains affiliate links, which means I may earn a small commission if you click and book—at no extra cost to you. I only share experiences and products I genuinely recommend and personally use or book for clients.

Itinerary Disclaimer:

This travel diary reflects my personal experience. While I strive to recommend reputable providers, activities and experiences may change due to seasonality, availability, or local conditions. Always check details with suppliers before booking.