boxofdelights

Oh, what fun! It is not completely impossible that I will be in that part of the country for a few overlapping days. I'll definitely let you know if I am.

Montreal airport has a good city bus that goes into the city, making a few stops at key metro stations and hotels. It's called route 747, and the fare you pay for that bus is good for any rides for the next 24h. And the train station is connected to a metro station and is centrally located. So that part's easy.

My favourite cheap place to stay in Toronto is a summer-only option. So I don't really have accommodation advice in either city off the top of my head. When I arrive at Toronto airport without either an expense account or my very helpful brother meeting me, I always take the Toronto Airport Express bus http://www.torontoairportexpress.com/ which is reasonably convenient but not as extravagant as a taxi. At U of T, is Mungo interested in programs at the main / downtown / St George campus? In recent years there are more programs located at U of T Scarborough or U of T Mississauga, but I don't think that someone who wants the downtown experience would enjoy those campuses in the same way as the "real" U of T or as McGill.

Train advice: Sign up for VIA Preference, both of you. One trip and the joining bonus might not give you enough points to do something with, but if he ends up living in either city for a few years you'll probably go again. And unlike airline bonus schemes, free is really free with VIA rewards travel. Pay attention to whether your train has checked bag service, and what the limits are on how much you can carry with you in the car. (It varies from train to train, some of them being particularly stringent). You can get the cheapest tickets by him being able to prove he is under 26, and by either booking early or checking out "Express Deals" for last minute sales. (Sometimes you can also get a good deal on first class, which includes a good meal and drinks.)