I Spent the First Week of the 2026 Winter Olympics in Milan—Here Are 11 Ways to Soak Up the Spirit Beyond the Games

OMG bestie, you are going to have the absolute best time! Milan is always cool, but during the 2026 Winter Olympics? It is going to be on a whole other level! I just got back from spending the first week there, and even though I didn’t have tickets to every single event, I felt like I was right in the middle of the action the whole time. The city is literally glowing with Olympic spirit! I put together this huge guide for you so you don’t miss a single thing. Forget those boring travel books—this is the real deal on where to go, what to eat, and how to feel like a local while everyone else is acting like a confused tourist. Get your warm coat ready because we are going to Milan!

1. Climb the Roof of the Duomo

You cannot go to Milan and not see the Duomo. It is that giant, spiky white church in the middle of the city. But here is the secret: don’t just go inside. You have to go to the roof! It costs exactly $18 for a ticket to take the stairs, and it is worth every penny. When you are up there, you are surrounded by these amazing stone carvings that look like lace. For the best photo, walk all the way to the back part of the roof where the spires are really close together. Stand right in the middle and have your friend take a photo from a lower angle. It makes you look like you’re in a fairy tale! Plus, on a clear winter day, you can actually see the snowy Alps in the distance where the skiing is happening! It is the coolest way to see the Olympic mountains from the city.

2. Eat a Panzerotto at Luini

Once you get down from the roof, you’re going to be hungry. Walk two minutes over to a place called Luini. You’ll see a line, but don’t worry! It moves super fast. You are going to order the “Panzerotto Pomodoro e Mozzarella.” It costs $4. It is basically a fluffy, fried dough pocket filled with hot cheese and tomato sauce. It is the ultimate winter comfort food. Stand on the sidewalk right outside with all the other locals and eat it while it’s steaming hot. Don’t try to be fancy and sit down; just wrap your hands around that warm paper bag and enjoy. It is the cheapest and most delicious lunch in the whole city!

3. Spin for Luck in the Galleria

Right next to the Duomo is the Galleria Vittorio Emanuele II. It’s a huge shopping mall but it looks like a palace with a glass ceiling. It’s totally free to walk through! Look for the mosaic of a bull on the floor. You’ll see a crowd of people standing around it. Legend says if you put your right heel on the bull’s, uh, “private parts” and spin around three times, it brings you good luck. I did it and then found a $20 bill later, so I’m a believer! Stand there and watch the tourists for a bit—it’s great people-watching. After you spin, look up at the glass dome. It looks amazing when the winter sun hits it.

4. Aperitivo by the Navigli Canals

This is my favorite part of the day! In Milan, they do “Aperitivo” around 6:00 PM. It’s like a happy hour but better. Go to the Navigli district—it’s an area with two big canals lined with bars. You pay about $15 for a drink (get a Spritz!), and that price includes a huge plate of snacks like tiny sandwiches, pasta, and olives. Some places even have a buffet! Sit at a table right by the water. The lights from the bars reflect on the canal and it looks so pretty. It’s the best way to rest your feet after a long day of walking. Plus, everyone there will be talking about the Olympic scores, so the energy is super high!

5. Join the Crowd at the Fan Zones

You don’t need a $200 ticket to feel the Olympic hype! Go to Piazza Gae Aulenti. It’s this super modern area with tall buildings and a big circular square. During the Games, they set up massive TV screens here for free. It’s like a giant party! Everyone wears their country’s colors, and when someone wins a medal, the whole place goes crazy. Budget $0 for this because it’s totally free! Stand near the edge of the fountain for the best view of the screen. It’s way more fun than watching in a hotel room because you’re surrounded by fans from all over the world cheering and screaming.

6. Drink Your Coffee Like a Pro

Don’t you dare go into a cafe and sit at a table for a coffee! If you sit down, they will charge you $6 for a tiny espresso. Instead, do what the Italians do. Walk up to the bar, pay $1.50 at the register first, take your receipt to the person making the coffee, and drink it while standing up. Say “Un caffè, per favore” and they’ll give you a quick shot of energy. It’s fast, it’s cheap, and you look like you actually live there. My favorite spot is any “Pasticceria” you see with a gold sign. The coffee is always strong and perfect for keeping you warm in the February chill.

7. Get a Thick Slice of Pizza at Spontini

If you want pizza that isn’t thin and floppy, go to Spontini. They only make one kind of pizza: a thick, soft crust with tons of melted cheese and a slightly spicy tomato sauce. A big slice and a soda will cost you $9. It is so filling! The best one is near the Corso Buenos Aires shopping street. There aren’t many chairs, so you usually stand at a tall counter to eat. It’s greasy and salty and perfect after a day of freezing your toes off at the Olympic fan zones. It’s basically a hug in food form.

8. Walk the Grounds of the Sforzesco Castle

Milan has a real-life castle right in the middle of the city! It’s called Castello Sforzesco. You can walk through the courtyards for free, which is awesome. It’s huge and made of red brick. Stand in the middle of the main courtyard and look up at the big tower—it’s a great spot for a selfie without a million people in the background. If you want to go into the museums inside, it’s about $12, but honestly, just walking through the grounds is cool enough. Behind the castle is a giant park called Parco Sempione. It’s where all the locals go to run or walk their dogs. It’s a great place to clear your head if the Olympic crowds get too loud.

9. Window Shop in the Brera District

Brera is the “artist” neighborhood and it is so cute! The streets are narrow and made of cobblestones. It looks like a movie set. Everything here is expensive, so I usually just window shop. You’ll see fancy perfume stores and art galleries. Stand on the corner of Via Brera and Via Fiori Chiari for the best “vibe” photo. It’s super romantic and cozy. Even if you don’t buy anything, it’s fun to pretend you’re a millionaire for an hour. Keep an eye out for small boutiques selling handmade leather gloves—they are perfect for the winter weather and usually cost around $40.

10. Melted Chocolate Gelato

I know what you’re thinking: “Gelato in the winter?” YES. You have to go to Cioccolatitaliani. They have a fountain of melted chocolate that they pour into the bottom of your cone before they add the ice cream. It is life-changing! A cone with two scoops costs $5. Get the dark chocolate and the hazelnut (nocciola) flavors. Standing on a street corner in the cold with a cone of chocolate-filled gelato is a true Milan experience. It’s so rich and yummy you won’t even care that your nose is cold!

11. Ride the Old Orange Trams

Instead of taking the boring subway everywhere, look for the old orange trams. They are from the 1920s and have wooden benches inside and glass lamps. It costs $2.50 for a ticket (you can just tap your credit card on the machine inside). It’s like a moving museum! Take Line 1—it goes past all the big landmarks. Sit near the window and watch the city go by. It’s a really relaxing way to see the sights without having to walk miles and miles. Plus, it’s a great way to warm up while you head to your next Olympic party!

Budget vs. Balling Out: What Will It Cost?

Planning your money is important so you don’t run out of cash before the gold medal rounds! Here is a quick look at what you might spend per day in Milan.

I am seriously so excited for you! Milan is going to be electric during the Olympics. Make sure you take a million photos and eat your weight in pasta. If you want more tips or want to see photos of my trip to help you plan, you have to join our travel group! We talk about all the best deals and secret spots every single day. Go over to https://www.facebook.com/CheaptravelVIP.FL and join the family! Can’t wait to hear all about your trip when you get back! Safe travels!