The very first thing you need to do when planning your trip is to decide what time of the year you want to go. There are lots of things to factor in, but the four main ones are: crowds, holidays, the kids' school calendar and weather.
The following are, in my opinion, the best times to go because the weather is great and the crowds are low.
1) January 1st - February 12th
2) April and May (after Spring Break and before school gets out)- The International Flower and Garden Festival at Epcot adds a beautiful spring touch and on the weekends there is a concert series featuring artists from the 60s and 70s.
3) October and Early November (before Thanksgiving) - Magic Kingdom plays host to Mickey's Not So Scary Halloween Party and The International Food and Wine Festival is going on at Epcot
4) Early December (before Christmas break) - the parks are decorated for Christmas and it's "value season" so the rooms are discounted
Are you noticing a pattern? I know that the great state of Texas would not appreciate me telling people to pull their kids out of school to go on vacation, but the bottom line is - when your kids are on break, so are everyone else's. If you can't swing the vacation time or don't want your children to be truant, here are my choices for other times of the year.
1) If you must schedule around a holiday, shoot for Easter. It usually falls within the regular season so you won't pay a higher room rate. The crowds will be heavier over the weekend, but the weather should be great.
2) Mid to late August is considered part of "value season" at DW. The weather will be hot and very humid, but the heat and fears of hurricanes keep the crowds at bay. You should get a sizable discount on your resort and the only thing hurricanes bring to Orlando is rain.
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