I spent a few days in Milan in June 2021 with my brother during COVID times. Honestly, we only went there because there was a good cheap flight from New York, and we were planning to go somewhere else after. It was basically a stopover point, which I think is actually a smart travel strategy – fly somewhere cheap, stay a few days, then continue to your real destination.
And that’s exactly what Milan is good for – a quick stopover. Overall the city was pretty blah. I didn’t hate it, didn’t love it, just felt kind of meh about the whole place.
What Milan Actually Is
Milan’s got about 1.4 million people and it’s Italy’s economic capital and fashion center. But honestly, most of the city feels pretty old and dusty – not in a charming historic way like Rome, but in a kind of run-down, second-world way that reminded me of the Balkans.
The only really nice part is the center square around the Duomo Cathedral, which is genuinely beautiful. That whole area plus the fancy shopping street (Quadrilatero della Moda) where they have all the high-end fashion stuff – that’s basically the highlight of the city. Everything else feels kind of blah.
The History That Made This Fashion Capital
From Roman City to Fashion Powerhouse
- Roman origins: Originally called Mediolanum, but you don’t really feel the ancient history like in Rome
- Medieval and Renaissance: Ruled by powerful families like Visconti and Sforza, who built impressive stuff including the Duomo
- Industrial powerhouse: Became Italy’s industrial and financial center in 19th-20th centuries
- Fashion capital: Post-WWII, became one of world’s fashion capitals alongside Paris and New York
- Modern business hub: Today it’s Italy’s economic center, but infrastructure feels dated
All the major Italian fashion houses are based here – Prada, Versace, Dolce & Gabbana – which explains the incredible attention to style throughout the city.
Architecture: One Amazing Cathedral, Everything Else Meh
The Duomo and the square around it (Piazza del Duomo) are genuinely spectacular – the Gothic cathedral is massive and incredibly detailed. The whole square area feels like what you’d expect from an Italian city center.
Main Areas Worth Checking Out
- Duomo area: The cathedral and main square – definitely the highlight
- Quadrilatero della Moda: High-end shopping district with all the fashion brands
- Galleria Vittorio Emanuele II: Beautiful 19th-century shopping arcade
- Brera: Supposed to be artsy neighborhood, though didn’t impress me much
- Navigli: Canal district with bars and restaurants
The problem is that outside of the main tourist area, Milan just feels kind of grimy and second-world. It doesn’t have that polished European capital feel you’d expect.
The Duomo: The One Must-See Thing
The Milan Cathedral is genuinely impressive and basically the only must-see attraction in the city.
What Makes It Worth Seeing
- Gothic architecture: Incredibly detailed façade with tons of spires and statues
- Size: It’s massive and dominates the whole square
- Rooftop access: You can go up on the roof and walk around the spires
- Interior: Beautiful stained glass and religious art
- The square: Whole area around cathedral is well-designed
This is basically the one area of Milan that lives up to expectations of what an Italian city should look like.
People and the Italian Style Factor
Milan really is a fashion city – people dress way better than in most places. Lots of those classy brown loafers, tailored clothes, that effortless Italian style thing. Even regular people on the street look put-together.
English is okay in the center and fashion/business areas, better than in Rome but still not amazing. Italians are generally friendly and expressive.
The vibe is less touristy than Rome, more business-focused, but also less charming. It feels more like a working city rather than a tourist destination.
Summer Heat and Infrastructure Problems
June was already getting hot and humid, and here’s a major problem – there’s not much AC anywhere. Restaurants, hotels, public spaces – air conditioning just isn’t standard in Italy like it is elsewhere.
The infrastructure reality is that Italy’s infrastructure is honestly pretty bad. WiFi is spotty, internet speeds aren’t great, public services feel dated. For a major European business center, Milan feels surprisingly lacking in modern infrastructure.
Seasonal Considerations
- Summer (June-August): Hot and humid with terrible AC situation
- Winter (December-February): Probably gray, cold, and depressing
- Spring (March-May): Best weather for visiting
- Fall (September-November): Decent weather but can be rainy
The lack of proper AC in summer is a real problem if you’re trying to work or just be comfortable.
Shopping and Fashion District
Since Milan is a fashion capital, the shopping scene is obviously a big draw.
Where to Shop
- Quadrilatero della Moda: High-end fashion district with all major Italian and international brands
- Galleria Vittorio Emanuele II: Beautiful shopping arcade connected to Duomo square
What to expect: Extremely expensive, beautifully designed stores, well-dressed staff and customers. Even if you’re not buying anything, it’s interesting to see how seriously they take fashion here.
Food Scene: Classic Italian, Nothing Special
Milan’s food scene is solid Italian cuisine but nothing particularly unique to the city.
Local Specialties
- Risotto alla milanese: Rice dish with saffron
- Cotoletta alla milanese: Breaded veal cutlet
- Panettone: Sweet bread that originated here
- Aperitivo culture: Pre-dinner drinks and snacks
Pricing
- Meals: €15-35 (expensive in center)
- Coffee: €1-3
- Aperitivo: €8-15
- Daily food budget: €40-70
The food is good but you’re paying premium prices, especially in the fashion district.
Nightlife: Sophisticated Scene
Milan’s nightlife is more sophisticated than party-focused – it’s about aperitivo culture, wine bars, and looking stylish.
- Navigli district: Canal area with bars and restaurants, main nightlife zone
- Aperitivo culture: 6-8 PM drinks with free snacks, very Italian tradition
- Fashion crowd: Social scene revolves around fashion industry people
It’s more about seeing and being seen than wild partying. Dress code is important – you need to look good to fit in.
Tourist Attractions: Not Many
The Main Stuff
- Duomo and square: Obviously the highlight
- La Scala opera house: Famous but expensive and often sold out
- Sforza Castle: Historic castle with museums, decent but not amazing
- Brera district: Art galleries and boutiques
- Navigli canals: Nice for evening walk
Day Trip Options
- Lake Como: About an hour away, much more scenic
- Lake Maggiore: Another lake option
Honestly, you can see everything worthwhile in Milan in 1-2 days. There just isn’t that much compared to Rome or other major Italian cities.
Digital Nomad Assessment: Don’t Even Think About It
Why Milan Doesn’t Work for Remote Work:
- Infrastructure problems – WiFi is unreliable, internet speeds are mediocre
- No AC – summer working conditions are terrible
- High costs – expensive rent and living costs for what you get
- Italian bureaucracy is notoriously complicated
- Very different work culture and business pace
Digital Nomad Rating: 3/10
Better alternatives: If you want Italy for remote work, try smaller cities with lower costs. Milan combines high prices of a major city with second-world infrastructure.
The Dusty, Second-World Reality
This might sound harsh, but Milan just feels kind of dusty and run-down outside of the main tourist/fashion areas. It doesn’t have that polished, first-world feeling you get in cities like Zurich or Amsterdam.
What I Mean by “Dusty”
- Buildings look weathered and not well-maintained
- Infrastructure feels dated
- Public spaces aren’t that clean or modern
- Outside the center, it feels kind of Balkan-esque
It’s not terrible, just not what you’d expect from a major European business center.
Cost Reality
Uses the Euro, expensive in the center but not as bad as some other major cities.
Daily Costs
- Accommodation: €70-150/night for decent places
- Food and drinks: €50-80/day
- Transport: €2 per metro ride
- Total daily budget: €100-180
Expensive but manageable for a short visit.
Transportation and Practical Stuff
- Getting around: Decent metro system, walkable center, but public transport feels dated
- Airport connections: Malpensa and Linate airports connect to major destinations – good for stopover strategies
- Regional transport: Good train connections to other Italian cities and Switzerland
Who Should (And Shouldn’t) Visit Milan
Good For:
- Fashion enthusiasts who want to see the industry center
- People doing an Italy tour who want to see the business side
- Travelers using it as a stopover point
- Architecture fans who want to see the Duomo
- Business travelers who need to be there
Skip It If:
- You have limited time in Italy (go to Rome or Florence instead)
- You’re looking for classic Italian charm
- You want great value for money
- You’re planning a longer stay
- You prefer polished, modern city infrastructure
Milan vs. Other Italian Cities
Versus Rome: Rome is way better for tourism, more history and attractions
Versus Florence: Florence is more charming and artistic
Versus Venice: Venice is more romantic and unique
Versus Naples: Naples is more authentic but chaotic
Milan is the least touristy major Italian city, but also the least interesting for most travelers.
My Honest Bottom Line
Overall Rating: 6/10
Milan is fine for what it is – a business and fashion center with one spectacular cathedral. The Duomo really is impressive, the fashion district is interesting to see, and people dress incredibly well. But overall, the city just feels kind of blah.
It’s dusty, the infrastructure is lacking, and outside of the main square and shopping area, it doesn’t have much charm. It feels more like a second-world business city than a first-world European capital.
Perfect as a Stopover
2-3 days max – see the Duomo, check out the fashion scene, then move on. This is exactly what Milan excels at.
Not Worth a Special Trip
Unless you’re really into fashion or have business there, there are better places to spend your time in Italy.
The Stopover Strategy
Milan works best as part of a larger Italy trip or as a cheap flight destination before going somewhere else. It’s functional but not particularly inspiring.
The smart approach: Fly in cheap, spend a couple days seeing the cathedral and fashion district, then get on a train to somewhere more interesting like Rome, Florence, or the lakes.
Final Verdict
Decent stopover city, terrible long-term destination. See the Duomo, experience the fashion culture if you’re into that, buy some beautiful Italian clothes, then move on to somewhere with more charm.
Milan delivers exactly what it promises – business efficiency and fashion excellence – but doesn’t offer the romantic Italian experience most people are looking for. Know what you’re getting and plan accordingly.
Sometimes cities serve specific functions rather than being complete destinations, and Milan falls into that category perfectly.
Have you used Milan as a stopover city, or did you find more to love than I did? Did the fashion scene and Duomo make up for the infrastructure issues? Share your Milan stopover strategies in the comments!
