For what it's worth, here's my process for booking our upcoming fall trip to WDW.
The first thing we do is book our time off work. In my case that has to be done in January. We wanted to be at WDW for the 40th anniversary (the weekend of Oct. 1) and we need to be in PEI for Thanksgiving weekend (the following weekend) so that is what dictated our travel dates.
At 180 days I booked the dining reservations, based on available park hours and Extra Magic Hours evenings. Yes, I did book dining before hotel and flights!
Now I'm looking for a WDW promotion, specifically I'm looking for the usual fall free dining promotion. I'm hoping this will come out in the next couple of weeks, certainly by early May if they follow the pattern of the past couple of years.
By July I'll be looking for flights. The best prices will be if you can fly on Tuesday, Wednesday or Thursday (avoiding the weekends) and make the reservation on a Tuesday. Because of our situation we can travel one way mid-week but must travel the other way on the weekend so our flights may be a bit more expensive but there's no help for it right now and I realize that.
We prefer to fly through a US connection on a US carrier, and we have been getting the best flight times and prices with Continental. We fly out of Halifax, through Newark, early morning to arrive in Orlando by early afternoon. Departing Orlando mid-afternoon arriving in Halifax very late evening. Last year this cost us $459.01 Canadian per person, all fees included. We thought that was a good price. I booked it at 12am Wednesday morning (11pm Tuesday night in New York) July 27 for a Dec. 1st departure.
When we have our flights booked I'll get the
travel agent to add that information to our Disney package reservation and arrange for Magical Express.
This is a very long message but I hope it gives you an idea of what we have found to be a good process.