January direct (non stop) flights to Rome

I suggest that you go to a site like travelocity, orbitz or kayack and put in your travel dates and airports make sure you check the non-stop option . That will give you your options. When you have found an option, go to the airlines website and make your reservation through them.

I think your stuck with New York City. Make 1 stop and then there are lots of possibilities. Closest nonstop from Toronto would be Zurich, not every day, and a 7 to 8 hour train ride.

matrix.itasoftware.com shows lots of routes to Rome, all requiring a connection somewhere. In my view, Amsterdam is easier to handle than London Heathrow or Charles de Gaulle Paris because it is smaller. But Munich and Zurich are efficient and others also pop up. No reason to go through a US gateway. Total travelling time and cost are more important to me than small variations in airports. In the current security climate, all can be a test of patience and endurance. Not much can be done for your companion's nerves other than getting to airport plenty early and choosing a connection that allows lots of time too.

I agree that you aren't going to get a direct flight. But there are plenty with only one connection. Looks like your friend will just have to deal with it. If you filter for the quickest flights on Kayak.com, you'll easily be able to sort thru your options. Pick one that gives plenty of time at the connecting stop.

Thank you all for your useful advice.