This is the most difficult question that you have to answer before going to Walt Disney World. Factors to consider are Disney events during the year, school vacation, weather and crowds. There are advantages and disadvantages to each time of year. Let’s take these month by month.
January is tricky. You have New Year’s and the few days after as well as marathon weekend. Then things get less crowded. However, it is generally cold, not northeast cold, but cold (limited or no pool time). Then there are the attraction and restaurant closures for refurbishment.
February starts off similar to the end of January, then President’s week hits, which is a popular time for vacationers from all over the country.
As March comes, the weather is nicer in Florida. It’s not as unbearably hot as summer, but you can get your pool time in. The only problem is spring breakers. The end of March is also the beginning of the EPCOT Flower and Garden Festival. The festival goes from late March through early May. I have no green thumb what so ever, however this is a great event, I am just amazed at the plants and topiaries all around EPCOT. Throughout the festival there are also seminars on gardening with celebrity hosts, kid’s activities and food carts which were added in 2013. The festival is part of the reason why my wife and I like going to Walt Disney World in April. The weather is great and the Flower and Garden Festival is in full swing. There is also the Flower Power Concert Series. Down sides to April are if Easter week falls on the same week as April break from the northeast, then everybody in the country has that week off and it is extremely busy.
In May there are also a lot of activities. Star Wars weekends at Hollywood Studios run from weekends at the end of May through mid-June. Depending on how much of a Star Wars enthusiast or crazed fan you are, you may want to plan accordingly, and plan you must, if you want to see any special guests or do any activities while there. This event is only on Friday, Saturday and Sundays and really only affects Hollywood Studios those days. Also in May, the southern state schools are starting to get out and the crowds start to increase.
A downside to June is the weather starts to get real hot so be prepared. Also, almost every kid is on vacation by the end of the month. July, on July 4th there is an incredible fireworks display with double the amount of fireworks at the Magic Kingdom. July also kicks off the Sounds like summer concert series which lasts through mid-August. In July and August, it is HOT!!! However, everything indoors is air-conditioned (my wife actually packs a light sweater for when we are inside places). July and August are some of the most crowded times of the year. Many southern states go back to school in early to mid-August. This means that if you live up north, a late August trip is a good idea. Although it is very hot in June, we have found that the temperature difference in July and August isn’t too bad between Florida and the northeast. We have been sometimes when it’s actually been hotter back home than in Walt Disney World in these months. Not to mention, you always get that afternoon thunder shower, it’s like clockwork.
Now that we are into September doesn’t mean the weather is that much cooler. You also have hurricane season too. However, the crowds are considerably less since all kids are back in school. There is also a lot happening in September. Starting in early September through the first day or two of November is Mickey’s Not So Scary Halloween Party in the Magic Kingdom. This is a must if you are at Walt Disney World during this time period. Personally, I am not a Halloween fan, however the Halloween party is excellent. The trick or treating, character events, parade with the ride of the headless horseman and fireworks are just incredible. Late September also marks the start of the Food and Wine Festival at EPCOT. This is the tastiest event of them all. There are kiosks everywhere that serves all types of foods from around the globe. In addition to tasting these items, there are also seminars about wine and tastings, cooking and my personal favorite, the Samuel Adams sampling (time to pause for a refreshing beverage). October is a great time of year to go to Walt Disney World. It is probably the best in my opinion because of the Food and Wine Festival, Mickey’s Not So Scary Halloween Party, weather, and low crowds. The food and Wine festival goes until mid-November. The Food and Wine Festival always makes for busy weekends at EPCOT. November is also good, except for Thanksgiving week and weekend.
November is also the start of the Christmas season at Walt Disney World. The transformation between Halloween and Christmas at the Magic Kingdom is almost instantaneous. Through November and December on certain nights the Magic Kingdom plays host to Mickey’s Very Merry Christmas Party. During the party there are special character meet and greets, a parade and fireworks. Not to mention the decorations. Also at the Magic Kingdom is the nightly Castle Lighting Ceremony. This is one not to be missed. Even if you have seen pictures of the castle lit up, it does not compare to being there. When you get a spot to watch the castle light, stay there, you can see the parade and night-time fireworks almost one right after the other. This is also a good time to let your younger kids see the Magic Kingdom fireworks since they are not too late. At EPCOT, each country has a telling of their own holiday traditions. My wife and I were a little nervous about having our kids watch these (we didn’t know if seeing the different ways the holiday were celebrated would make them question their own Christmas and Santa Clause). If you have this concern, don’t worry, I recorded each one and my kid’s watch it over and over. They are incredible stories told by some amazing story tellers. Over at Hollywood Studios the Osborne Spectacle of Dancing Lights is not to be missed!!!! It is unbelievable! At Animal Kingdom they have Mickey’s Jingle Jungle Parade. The characters are dressed in their Christmas outfits and the delicious smell of hot chocolate wafts from Minnie’s parade float. The hotel lobbies are also an attraction that can’t be missed this time of year. Namely the Yacht and Beach Club, Boardwalk, Animal Kingdom Lodge, Wilderness Lodge and especially the Grand Floridian with life-size gingerbread house. Crowds in December are at their best and worst. The first two to three weeks in December the Crowds are minimal. However, after this time avoid going to Walt Disney World at all costs. The crowds are horrible: wall to wall people.
Hopefully this will help with when deciding to go.

Please leave a comment on here, like us on Facebook at Disneyhelp or follow us on Twitter @Disneyhelp.