Only allowed to travel to connecting airport

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This is an unusual (and irritating) situation. To answer your questions:

  1. Yes, if there is sufficient time and he is able to pass immigration in Rome. Since he has checked luggage and the first airline is only willing to check his bags as far as Rome, he'll need to go through immigration, baggage claim, and customs, take the bags to the check-in counter for the second airline, and check-in before the airline's deadline. (This would be much easier if he didn't have checked bags.) That can all take a while, especially if there are lines at immigration or his first flight is delayed. He'll also need the required documents to enter Italy, which you say he does. With checked bags, this is not practical unless his connection is at least a couple hours.

  2. This is where it gets more complicated. I don't know the airlines involved, but most all have language in their contracts of carriage that say that compliance with documentation requirements, including health forms, is the passenger's responsibility. The exact details will depend on the specific conditions attached to his ticket, but the airline could well argue that, since this is his fault, he has to pay the applicable change fee plus the difference in fare, which could be substantial. The airline would also have to have a flight with space available to a neighboring country. It's always possible someone could take mercy on him and make an exception, but there's no assurance that would happen.

    Of course, if he stays in A or Rome to get the vaccination, he'll be responsible for the fees to change his ticket as well unless the airline staff waives them.

  3. Airline tickets must generally be used in order. If you miss one flight without changing them, all the rest of the segments on the itinerary are cancelled. Assuming the tickets are changeable (most are), he could pay the change fee and difference in fare to change his ticket to come home. It's hard to predict what this will cost (possibly just the change fee), as the airline will reprice the ticket based on the new itinerary. If this is a possibility, you can contact the airline and ask them to work out what it would cost; purchasing a new ticket home from the cheapest available airline can sometimes make more sense depending on the details.

Airlines generally use the same database, Timatic, to determine whether vaccination certificates are required, so there's a decent chance the check-in staff in Rome will see the same requirements the staff saw in A. Whether or not they enforce it, or the advisability of attempting to evade public health regulations, I cannot say.

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