My last trips have resulted in disappointment from 3 different European countries I've overhyped in my mind: Germany, Greece and Romania. For two of them those were my 2nd trips there (Germany & Greece).
It's true that it's easier to love some places from a far and the allure goes out the window when you're actually there.

I booked flights to Milan for this month. I'll stay in Milan and Bergamo each.
I've read stories where travelers share Milan's not a really nice city, etc. that's why I'll spend some days in Bergamo as well. My airline uses their airport anyway.

I've actually never hyped Italy in my mind. I know its historic, cultural and artistic importance. I know its language sounds beautiful and it has good food, amazing architecture and probably Milan's not exactly the best representative of either.
The thing is I don't fear not liking the buildings or food as much as I fear how I'll like the locals, the way the people act with strangers.

I have no tolerance for rude customer service Bucharest-style. Now the ones in Germany and Greece were good. There the issues were more like the cultures didn't match what I expected. I was lead to believe Greeks are so open and friendly you can make new friends everywhere. That's not my experience at all. I found them friendly only if they work in tourism, the rest are aloof. Not unfriendly, just uninterested in conversations with random strangers. I've had more of these pleasant encounters in Bratislava, Slovakia than in Athens or Thessaloniki. Maybe small island towns are different but the reason for my latest trips is to look for possible lands for expatriating to. As for Germany - I had good customer service but the strangers on buses, in trains were nt particularly my soul tribe kind of people. In other words, I didn't feel comfortable among Germans or rather their stoic nature.

While there are nations I've had almost only positive or mostly negative experiences with I have mixed experiences with Italians abroad. Some were pleasant, some nice, others not so. Also, Italy is culturally like several different countries - the North West is different than the North East, the Middle is different, and then you get Sardinia, the South continental parts of the boot, and Sicily. Sardinia and Sicily themselves are as large as some European countries. And then there's a German-speaking part, too.

Anyway - I've heard Milano locals aren't the friendliest but it's also filled with people from the South and East of Italy, too.
My question is how to prevent disappointment in the people? How not to expect too much from them in terms of friendliness? Should I go with no expectations?

There are rude people everywhere. And other cultures may have different styles what you may consider to be rude or unfriendly is normal par for the course for that culture. While i dont know where you are from, Americans especially have a problem with this - some expect everyone to chit chat and make small talk like they would at home and then call (insert country) rude.

Manage your expectations and don't let "rude" or "unfriendly" people ruin your trip. That's all you can do.

I have personally only encountered one rude person in all of my times in Italy. I moved on from it and barely have thought about the encounter since.

Otherwise, this is really a "you" concern more than anything.

No matter what country you visit, people have their own busy lives to get on with. They may be happy to have a brief chat with someone if they've a few minutes to spare but may be unlikely to invest in friendship with someone who is just passing through their town. This goes double if you don't have a shared language. Don't forget that cultures are different too. What is normal in one country may be considered off hand or impolite in another.

Go with no expectations as to encounters you might have and enjoy the ones which do arise, including those with fellow tourists. The unexpected is what will stay in your mind years down the track.

Hi tanek, My late DH and I got soooo hooked on Italy, we neglected other countries including our own USA.

Despite the stereotypical friendliness, be aware that there are three levels of saying 'goodbye': ciao should only be used with friends; arrivaderci more formal and what tourists should use; arrivaderla for older, most revered people.

As in other countries, always say hello (look up the Italian way!) when you enter a place of business. Just be polite.

We didn't get to Bergamo so I can't help there, but don't miss the Duomo (inside and the roof) in Milan. Maitaitom has a nice TR of Milan. You should look for his and all the other reports about Bella Italia! Have you looked into the nearby lakes? Stunning views. Please report back!

Wherever you go, that’s where you are. Try to live in the experience, in the moment and with the understanding that you ultimately determine what to bring home from your travels.

I don't have any good advice on the type of people you will meet but I think a lot has to do with your expectations. I can be very friendly when I want as I think people see me as a friendly person but if I'm not feeling it, forget it.

When I was in Milan, I went on a few tours. I was with a friend but did talk to people on my tours who were traveling solo. I had a nice time and felt Milan is short changed as I could have spent more time there. I was going to do a Bergamo do it myself side trip but was told not to bother. I have never been but trusted the person so went to Bologna instead.

My friend didn't like the trip as nothing went right for her. She also had her wallet with all her money and credit cards stolen as she was being careless. Today, she will tell you the best part was after her wallet was stolen while we were in Bologna, I got so tired of her running at top speed, I made her sit down at a café outside and just sit with a drink and sandwich.

Sure things are going to go wrong, some people aren't great but that doesn't mean you still can't have a nice time and just enjoy the time you have.

Are you hoping to meet friends or what?

In Greece language is going to be an issue unless you speak Greek. But in general they do tend to be open. Doesn't mean they're hoping to make a new best friend.

Germans have a reputation for a bit of a cold shield but if you make a connection they open up pretty much.

The problem with Milan is who will you run into? Most working people will be working. The rest will be out doing something. We're also back to the language issue.

IMO, yes.

Firstly I'd think about the people you meet. Are they busy people or calm people. Certainly big city types are not looking for a slow conversation.

In a similar way think about how you interact. Do you say hello (in local language) when you enter the shop, restaurant, hotel? In the countries you have mentioned do you ask "I would like..." rather than "I want...'. Do you fit into the local exchange process or do you say "Give me..'

If your interaction process is wrong for the culture then even people in customer service will react negatively even just in body language.

I've done it myself as a northern European when on holiday in the South.

I live in the north of Italy in the mountains. It's difficult to speak in general because your holiday will be made up of chance encounters with a small number of people.
However the stereotype of people who live in Milan does not correspond with what you are looking for. People in larger cities and especially Milan tend to be busy, in a hurry, a little wary, not especially patient.
For more pleasant interaction with locals choose some smaller destinations. Maybe Sarnico on Lake Iseo which is easy to reach from Bergamo. Always say Buongiorno and smile when you go into shops bars and restaurants. Don't expect to get a genuine response until the second or third time you see the same person.
The sort of friendly relaxed interaction you are looking for is something I noticed in out of the way towns and villages in Puglia....
But anywhere it takes time..... people are going about thier business and making friends with passing tourists is not a priority....it doesn't mean they're unfriendly

Go with an open mind, accept that in cities people are busy living their own lives, some people don't have time or are unable or want to talk to some random tourist in a, to them foreign,
language.
Restaurants are different in every country, but I know many Americans find the service slow or rude or whatever, when it is just the norm in that country. People take time to enjoy their meals, the waitstaff are generally professionals and are not hustling for a tip and the next set of bums on seats for another one, but are giving you the time and space to enjoy and digest your meal.
People at the next table may not appreciate you trying to strike up a conversation with them, they are not being rude, they just don't want to talk to you whilst enjoying a meal with family/friends.

Accept that you may not have any nice chats with people, be content with your own company, enjoy the places you are visiting and if you do end up with some conversation it is a bonus, not a requisite.

Germans don't talk on public transport, that's a thing. But I agree, eventually when you do get to know people they are charming and you can make lifelong friends. Just don't expect to make those friends on the S-Bahn!

Lavandula

To add to what others have said, travel for holidays is an optional choice and if you feel that it continues to disappoint, then there is no need to continue to travel. Some people simply don't find it particularly rewarding and it's totally okay to do other things instead. If your focus is to make connections with other people, there are much better ways of doing that.

This is an excellent point, thanks dreamon!

Milan is one of my favourite cities in Europe. You can get excellent food there, with a great variety, including restaurants specialising in the cuisine of all parts of Italy, and from other countries.

As for architecture, I'm not sure what styles interest you, but Milan has beautiful buildings spanning periods from the Romanesque (Basilica Sant'Ambrogio, 4th century) to the contemporary (various buildings in Piazza Gae Aulenti). These are just a very few examples. I would also recommend seeing the Sforzesco Castle, the Duomo, and the Bosco Verticale (Vertical Forest).

It's a bit difficult to address your problem with personal relationships in a foreign country. If you'll be in a country for only a short time, it's not easy to have conversations except at a very superficial level, especially if you and the people you meet don't have a common language. I live in a small town in central Italy; I came to live here 26 years ago, and have found it a very friendly town, more so than any other place I've lived before. However, when tourists are strolling through the town, it's not likely the townspeople will get into conversations with them. If an extroverted tourist were to stay longer than a few days, there's a good chance they'd have some interesting exchanges with other people. I don't know where you live; is it customary for people there to engage in conversation with passing foreigners?

Now this is the most difficult issue I find in your post: I think Milan is not going to help you with this decision. It's a huge city, and in a short stay, you won't learn much about living in Milan, let alone here in Italy. It's a very expensive city to live in. It's also not at all typical of Italy, precisely because it's so international.

I've never been to Bergamo, so I don't know what to advise you about visiting there. I know that the upper town has a lot of medieval buildings, while the lower town is modern.

The cuisine of Bergamo would be mostly regional Lombard specialties, such as polenta and roast meats.

For anyone visiting Italy, I strongly recommend doing a little research on regional specialties. For example, don't expect to find outstanding lasagna in Rome.

Bvlenci brought up an interesting point I missed from your original post about finding a location to become an expat.

You aren't going to get a full vibe of a location by passing through. You get a full view from staying there for an extended period of time and seeing the mundane. The boring day-to-day stuff. And this needs to be done over the course of a long period of time, more than the 90 days (tourist visa) would allow.

How you interact with people at home plays a huge part in how you interact in a new, permanent place.

You do it by becoming a "regular" at certain places. Via hobbies, religious services, community events, maybe work. You don't make friends at home without seeing and talking to people regularly.

And if you're trying to have a cold conversation with a local with being a tourist doing "research," on your living situation, you aren't likely to get what you're looking for, which is what you are probably running into. ETA: having fluency in the local language plays a huge role too.

I too missed the ex-pat bit. You need to look it to what visas and permits you need to live in any country, and be aware that Italian (and Spanish) bureaucracy is notorious.
Also note that you will have to take a driving test (theory and practical) if you wish to continue to drive in Europe having moved here, and that is a complicated and expensive thing. Even locals mostly fail first time.

You cannot tell how friendly the locals are from a fleeting visit, you need to stay for a longer time, up to your 90 days and actually live in the place and get a real feel for it. Even then not having the language will make interactions with many harder. Generally bigger cities are easier for expats, at least initially as more people are likely to speak English.
That said I moved from the UK to a small town in the Netherlands and learned Dutch very fast simply because I had to. People are friendly, but even after 40 plus years and raising three kids here, I wouldn't say I have any one Dutch person I would call a friend. It can be hard to make new friends as an adult when you have no shared youth or references. Doesn't have to be but that is my experience.

Hetismij has an important point. I learned Italian pretty quickly, partly because my husband is Italian, and I insisted on speaking only Italian at home. (I already knew some because I had studied at for a year at university.)

I met a lot of couples here in Italy, from England, Germany, and the Netherlands. I have observed that married couples have trouble learning the language, because they speak their native language at home, and they don't converse much with the local people. A good number have returned to their native countries because they have never really put down roots here, and as they get older they feel the need of social support.

Travel_Nerd has another excellent point. You make friends by participating in local activities. I'm active in the local church, the adult school, the archaeology club, and a local private organisation. But we also have very friendly neighbours, with whom we have neighborhood suppers, Christmas games, and just sitting around outside chatting in the summertime. Elderly and housebound people on our street can always count on a neighbour to pick up medicine at the pharmacy, or groceries at the supermarket.

Most people moving to Milan are moving to work. The last 18 months the media has been full of stories that home prices both rentals and purchase have soared with all the people leaving London for Milan. The people complaining aren't working poor so you know prices have gone up a fair bit.

In your post I kept reading “I read that Milanese aren’t the friendliest” or “I heard that they’re rude”. What’s this obsession with rude people? Milanese are busy people. They’re not actually rude. Are you going on vacation or searching for a social scene? You say that you’re staying in Bergamo without even knowing the city or its culture. Did you know that Bergamo, a city of just 170,000 people had more than 3 million tourists in 2023? It’s overwhelmed. It’s a beautiful city, with great food, friendly people, but without speaking language or knowing its nuances, you’ll be at a loss to communicate with them. I saw that you’re also looking for a potential expat place to live. A vacation IS NOT the time to do that or the way to do it. You need at minimum 90 days, and some say at least 6 months to get a feel before even exploring that path. One has to live in a country to experience it fully if one wants to eventually settle there. Speaking as one married to a northern Italian, and one who has lived in Italy in the past and will hopefully retire there, for me it’s different. I speak the language, albeit not fluently. I also speak 2 other languages aside from English. I loved Germany and Greece. Greece is our current favorite country to visit. The people are so friendly especially if one speaks a few words. They don’t care. Italians don’t really care either but, to be honest, it does help to know a few sentences. Lower your expectations, if you’re always being let down by countries you visit. As an American I’ve experienced more rudeness in the USA than anywhere else in the world that I’ve traveled, Italy included. Also, you speak about interactions with Italians abroad, but don’t give much detail about that. Anecdote does not equal data. Do your own research about Milan instead of relying on “I heard” or “I read”. It’s really disingenuous