Due to some feedback I received yesterday on my Disney post and because I had already decided to detail the planning process for anybody who might be overwhelmed with planning a Disney vacation, I will be trying to go through the process as well as I can. I'm sure everybody has their way of doing it, so I will be giving my own perspective. There are many books on the subject. I will try to let you know about some of them as I write these posts. I will intersperse the Disney posts with my regular writings.
One of the first things you should do when planning a Disney vacation is decide when to go. The two times we went to WDW were both the second week of May. This is a very good time to go, as the spring break crowds have left, and school has not let out yet. While riding the tram on our 2009 visit, the tram driver told us it was a good day for the Magic Kingdom the day we went as there were roughly 29,000 people there. This sounds like a lot except for when you think about how big the park is, 107 acres. With all the rides and shows that are available, this group of people is easily spread throughout the park so that congestion is minimal. This year, we are going in November. We were going to go the first full week until we were told, again by my cousin, that that is usually "Jersey Week." The New Jersey teachers have a convention in WDW, this year November 10 and 11, during which time they usually spend the week before visiting the parks with their families. I wanted to go in November to beat the Christmas rush and still be able to see the Christmas lights in all the parks and resorts, but we are not going the first week.
MouseSavers.com has a webpage that lists all the events that occur during the year at WDW. It tells you the best times to go based on the weather, which is another reason why May is a great time to go. The summers in Florida are unbearable, so I would recommend not going at that time. Look at MouseSavers list of events, especially the less-known events. Based on your likes and dislikes, you may want to avoid the weeks the cheerleading competitions go on or Pop Warner Week when the parks and value resorts are full of football players and cheerleaders. In June, they have Star Wars weekends, but the first week of June is also Gay Days.
Another website that lists a lot of the special events throughout the year and in the various parks is http://disneyworld.disney.go.com/special-events/.
AllEars.net is another site to check out: http://allears.net/pl/planning.htm#when.
A very helpful book that I purchased the first time we went is called PassPorter's Walt Disney World. Check it out at http://www.passporter.com/walt-disney-world-florida/home.html. They offer a sneak peek inside the book at http://www.passporterboards.com/concierge/show-ebook.php?ebookid=9781587710827&ebooktype=Browse with 44 free pages.