Things to know before travel
Other than pickpocketing strategies to look out for, some things I wish I knew before I traveled:
When you're seated at a restaurant, there will be a "coperto" charge of 9 euros (for 2 people). It seems to cover the cost of your seating (not a tax or tip).
Ask for a smoke-free zone to be seated in if you're not a smoker because there are a ton of smokers.
Public transport was very reliable in Milan but not in Rome. In Rome, you may come to the station stop and check if there is a board with arrival updates. It was reliable and up-to-date unlike Google maps data.
When traveling to Rome airport, I used S.I.T bus. We happened to arrive early for our bus and were able to get on the previous bus that was running late by 18 minutes. Make sure you plan your time-sensitive trips in advance.
Taxi drivers may cancel a ride and ask for higher fare in cash. Stand your ground or just leave if you're late. I fell for this trick because we were late to our Vatican tour.
Coffee/cappuccino costs about 1.5 euros unless you're in a tourist area (4-5 euros). Keep looking for cheaper options. Water costs cents if you purchase at a supermarket vs. 3-5 euros.
Most importantly: perhaps it's sad to confess but I only enjoyed Italy's cities during 4:00 - 8:00 in the morning. I like seeing people but constantly being conscious of the crowd takes away the attention from sightseeing. There is also no tourist noise in the early morning. The crowd and the noise make you feel as if the city is artificial or as if you're walking in a mall. I could fully immerse myself and appreciate history in early morning walks only. We also had colosseum tickets but because of the sun and crowd, it felt like I've seen more in gladiator movie. Oy oy oy! Too bad I was spent on the last day, otherwise I was planning to marvel at colosseum and the arch from the outside in the early morning.
I was also slightly worried about racism (central asian) and apprehension towards tourists (because there are too many), but at least on the surface, I noticed no such thing. It may also have had to do with us only visiting tourist cities. People were very friendly and tried to be helpful even if they didn't speak English. One time in Venice, ~ 4 in the morning, we were out of water and everything was closed, so I approached the workers to ask where I could find it. They offered me a bottle from their stock and did not even take the money I offered as payment.
Dressing: we were dressed fine but I was surprised to see super casual outfits, some of which were revealing, especially in Vatican!!! The cover-ups women were given were also somewhat transparent...So if you're short on time before a trip and don't have many outfit options, don't fret too much.
Edit to add: I enjoyed the trip overall, not saying it was bad. Just wishing I traveled off-season.