I just carried a backpack as my āpersonal itemā on the plane and it worked very well. I could see sending DS16 with a carry on suitcase and a backpack. He would have trouble with a large checked bag. The itinerary is Rome, Florence, Capri, Sorrento Region, Pompeii. I think there are 5 or 6 days in Rome. The teacher opted for fewer stops so that they could spend more time in each place, which we thought was wise.
On 3 trips to London from 2014 - 17 I got the Verizon international plan, but I did call home and also used all the features of my phone. That being said, these things may have changed since thenāa lot. I am not tech savvy and will have to show the suggestions to DH and DS14, who understands phones and computers far better than I do.
Iām not gonna comment from the parent end but I went to Italy for 10 days when I was 15 with a school group too. We had no disasters other than I spent the entire money my mom gave me for souvenirs on a blown glass for her early on in Venice (which she still has) and had to skip some lunches at the end (breakfasts and dinners were always covered). Life lessons! ;-). I think my mom gave me an emergency credit card too but I didnāt want to use it.
Just to be clear on the phone. It will work whether you get the international plan or not. If heās lost on the side of the road he can make a call or text or even turn on data and pull up a map. This will not be cheap but itās available in an emergency. If he turns off mobile data and do not make phone calls or texts via the phone service is what I would recommend. There is enough free wifi now that he can make calls or send messages via WhatsApp or any other message service for free. If you canāt trust him not to call/text off of wifi then I would investigate the International Plan.
Then heāll be just fine looking left, right, left crossing the street!
I donāt want to spoil the fun but this doesnāt seem very Disney-like. I suggest moving it to La Cava or non-Disney park section. Letās clear the way for actual Disney discussion.
Send him with a couple of travel-sized bottles of woolite. When you arrive at lodging, it is easy/quick to wash the previous dayās dirties in the sink and lay on a towel on the bed. By morning they are dry.
The main thing will be avoiding pickpockets. Zippered pockets or those waist money belts donāt even slow them down. I have a black leather necklace safe that I prefer for the passport. It is on a black leather thong, so could just be a funky necklace. If you see kids running amok, start swinging your arms around you wildly. Donāt worry if you wack one, if they get close enough to be wacked they were trying to steal from you. Heāll be pegged for what he is, but when he isnāt with the big group, stay silent when in doubt. I also usually avoided the traditional American dress, but as a teen boy he probably has nothing else.