I have a friend in Chile (Chilean citizen) with whom we wanted to go on a tour in Italy (January 2014).
I am from the USA, and to make things easier, I was planning to order a tour locally from somewhere like Globus or Virgin-Vacation for both of us, and then to arrive to Rome (me from USA, she from Chile) and meet there to start the tour (get picked up by the tour operators to hotel and so on).
However, she had some concerns recently, because she was speaking about this with their local tour agents. What they have told her, is that she could get deported if she does not present the right documentation for her stay in Italy (which I found very odd, but wanted to make sure once again that she will not have possibility of such problems). Another thing that they have told her is that supposedly it is compulsory for her to have tour insurance to be able to go to Italy? (Is this really true? even for me, tour insurance is optional, if I understand it correctly). My gut feeling tells me like those tour agents are just trying to sell her their own tour packages, however, I want to be sure what is true and what is not.
She will have a return ticket, obviously (with a connecting flight most likely in Spain or Portugal). The tour invoice should also include her name and information of each hotel and rail pass there (any problems of it being ordered from tour company in a different country?). I also know that Chileans have no need to have visas to go to Italy or any Schengen area.