You have to travel Italy from Canada without taking any Transit in other Schengen states if you dont take any Schengen Visa , but it will be hard to find such flight . I used RTD only for Germany ( which is visa free travel and has direct connectivity with Canada ) . Its better to have a Schengen visa and Travel without any prejudice. To get a Schengen Visa is not a difficult issue . The thing is very important that while you are moving between Schengen states , you must have a valid visa. Although i took France visa last time but i missed the validity date so i used only One country and that is Germany . If you need cheap air ticket for italy and Canada vice versa -- there must be Transit destination , so technically to travel italy , you should posses a Visa from Either France ,or Denmark or Nederland or any other Schengen country which required visa . then travel without any tension and lots of cheap ticketing option will be in in your pocket