We normally travel in February and it's never seems to be warm enough to swim and relax in the sun. Mornings and evenings get cooler.
We were at WDW this past October. Wonderful weather until the last days as a cold front had moved in and the mornings were chilly. (Late October.) We swam just about everyday and it was truly a highlight. I wish the kids' school still had a Fall break. It's getting too hard on DD to be out of school. Because of this our trips will now be when the children will miss the least number of days in school.
The weather was a trade off with slightly higher crowds.
We had a blast at "Mickey's Party" as my children call it, (DD11, DS5, DS3). If you tell them Mickey is having a party, they want to be there. We attended on the first night of parties and it didn't seem too crowded; I've heard 10/31 party can be very crowded.
The Food and Wine festival was an enjoyable experience. We did the Grand Tastings dinner and really enjoyed it. There seemed to be more to enjoy in October than when we travel in February.
Our next "holiday" trip will be for Christmas sometime, so that we can do Mickey's Very Merry Christmas Party. Like I said, any Mickey Party is good for our family! LOL! Although I know we would love to spend every Halloween with Mickey. (I think we might have to move within driving range of WDW. LOL!)
I'm sure you will enjoy your trip no matter when you go. Mickey is always the best!
Lori
6/1997 Off site, 2/2000 Off site, 2/2001 Poly, 10/2001 POFQ, AKL & Magic, 1/2002 ASMo & AKL