If you would like to take part in organized wine tours abroad but you would prefer a trip that is organized from Toronto, there are a number of possibilities. Steve Thurlow and Tony Aspler are based in Toronto, and Billy Munnelly is based in Prince Edward County. They typically run one or more wine tours abroad annually. Check their websites for details on upcoming tours.
The Opimian Society is a national non-profit wine purchasing co-operative. Its Toronto chapter runs several overseas tours a year.
Further afield but still in Canada, Fine Vintage Ltd is owned and operated by James McCluer who is based in Vancouver and is one of a small number of Masters of Wine in all of North America. It describes itself as the largest luxury wine tour company in Canada and facilitates wine tours to selected countries, hosted by a local Master of Wine. Follow their link for this years offerings. It also offers the WSET program, both in Toronto and other cities across Canada and the United States.
However, if you decide to travel independently, check out Accommodation for options.