Took our first trip to WDW in February 2017 and plan to return in late November/early December 2018. Last time I booked the following way for 2 adults and 2 kids (5,9) Booked everything in early November 2016 Tickets: Bought on the Disney Website with the 25% off Canadian Discount Flight and Hotel: Booked together on Westjet Vacation Site. Flight was direct to Orlando from Kitchener (Westjet no longer offers this flight) Booked a standard room at AKL (7 nights with 25% off room deal) but got lucky and was upgraded to Savannah View Room when we arrived without asking Price seems really good after following what a similar trip would cost all though 2017 What sites do you use to book or do you use an agent? Do you book flight and hotel separately? How far ahead do you usually book? We are in the Kitchener/Waterloo area and my only plan so far is to once again purchase the tickets from Disney with the 20% off deal for Canadians they are currently offering.