I live in Naples. Have quite a bit of advice I can give. I will PM you later, but here are just a few.
Toilet Paper........ok, here in Naples, toilet paper is nonexistent unless you are in a really nice place. McDonalds usually does have TP, but they also have paper napkins dispensers attached to the trashcans, so IF he needs TP, just have him grab some napkins BEFORE going in the bathroom. However, my suggestion is that you buy one of those bulk packages of Kleenex tissues....the small pocket sizes they have you buy little kids for school. This is what they sell to people at intersections. Everyone uses them. It is also customary that if you use the bathroom (and they are beyond disgusting) in a bar (cafe), you purchase something. Also, tipping for attended bathrooms is customary. Example....McDonalds in Piazza Garibaldi is attended and they do expect something (E10 cent is enough).
Pickpockets...yes, they are a problem. Make sure you tell your son to NOT allow anyone to touch him. The local salesmen on the street have learned to sell belts as a way to draw your attention from theft. THey will approach you and insist you need a belt (we all know American boys wear their pants loose). The salesman will come to you and grab your pants and give them an up and down shake...while his hands are searching your pockets. Stay away from beggers. Don't give them anything. THey usually have their little kids do the work for them. The kids will latch on to your pants and not let go. Stop them before they get to you. JUst place your hand out on their head to avoid further contact. Demand NO! THey usually give up. Remember...if you refuse to give them anything, it helps the locals as they will go away for good. I get much entertainment from the kids.......one little girl in the Galleria Umberto across from the S Carlo has a fake limp. Once the people walk away, she starts skipping and running around. SHe is about 3 years old...they learn early.
Bring anything you will need for headaches, upset stomach, etc. THese things are not easily available and many of our common items are not found here.
Rainy season is almost done. Weather here is hit or miss with cold and rain.
Make sure he gets a sandwich with buffalo mozzarella (if in this area). Also, get the pizza. Nothing like it on Earth. Same goes for gelato. Bet ya never saw a pizza with corn, french fries and hot dog slices have ya? Oh and there is no pepperoni here. If you ask for it, you will get green peppers.
Never pay full price. If a vender says that pair of sunglasses is E20, tell him E10....you can even get brave and tell him 2 pair for E15. If he tries to go up in price from 10 for 1 pair, tell him no and walk away...they will chase you down to sell for price you insist. Don't fall for "You are my friend. I will sell for cheap". or "It is the end of the day......I sell cheap". THey are lying. ALso, NONE of the stuff they sell is the real deal. No Oakley, no Gucci,. More like Fauxly and Gotcha! (this is what we call them). Don't fall for the guy on the
scooter who tells you he has a great deal on a camcorder. It was stolen and he will do a switch if you buy it. You will get a box of rocks. ANyway, just be aware of your surroundings.
Oh, my fav is the vendors who suddenly pack their stuff and run. They have no license to sell and the police is coming. What entertainment.
Check for service fees for credit/debit purchases. Usually there is a 3% fee of the total purchase for international purchses. Be aware of the Euro coins. Ones and twos look the same....small difference in size. Same with 20 and 50 cents. At least learn "thank you" and "please" in Italian.
Don't walk in front of a scooter or a Smart car. THey don't stop for anyone. Don't fall behind in the crowd as they walk across the street. IF there is a break in pedestrian traffic, you bet the next car will go and so will everyone behind him.
Have anymore questions, PM me.