For some reason, as soon as summer is over I begin thinking about the holiday season. This time is one of the best times to go visit Walt Disney World (with the exception of Thanksgiving week and the week between Christmas and new year).
Schools are back in session so the parks are less crowded, the summer humidity begins to fade and nobody decorates for any holiday like Disney does. Making it even more irrisistable is the free dining promotion Disney is offering for those traveling Sept. 27 through Dec. 17th. Disney has never extended free dining like this before! It's like getting the all inclusive free.
If you're going to be in Disney during the holidays - and by that I mean Halloween, Thanksgiving and Christmas - you'll want to consider one of Disney's special events such as Mickey's Not-So-Scary Halloween Party or Mickey's Very Merry Christmas Party. These events take place on specified nights after the Magic Kingdom closes around 7 p.m. It does cost an extra admission price but I believe it's worth it.
In 2007, I went to the Mickey's Very Merry Christmas Party in the Magic Kingdom. It was not crowded (they limit the amout of tickets they sell for this event). There were special parades and performances, they made it snow on Main Streetand they served free cider, hot cocoa and cookies throughout the park. It was very festive. Even the stores have special merchandise that they sell only during the party.
I definitely recommend spending time during the holidays seeing some of the amazing decorating Disney does.
One of my favorites is the Gingerbread House in the lobby of the Grand Floridian resort (pictured above). This amazing life-size structure is made completely of gingerbread and icing. It's been featured on the Travel Channel and is a must-see if you're in Disney during the holidays. You can even purchase miniature replicas of the ginger bread house to take home (though that might be challenging to take on a plane!).
Like everyone else, Disney no longer waits till after Thanksgiving to put up their Christmas decorations.
Disney uses 150 tractor trailer loads of decorations for Christmas throughout the property and usually begins putting them up in early November. You can be certain the Magic Kingdom will be decorated by November 10th, the first night of Mickey's Very Merry Christmas Party.

It's rumored that Disney is going to go back to allowing guests to make dining reservations 180 days prior to their arrival. It's currently 90 days. This is good except for those booking last minute trips. And there is a pretty big trend going on right now where people are booking just a few months out.
There are so many restaurant choices in Disney that you really have to research them and check out their menus. http://disneyworld.disney.go.com/restaurants
Some reservations are difficult to get even at 180 days out. LeCellier, Yachtsman Steakhouse, dining with the princesses in the castle and Victoria and Alberts are just a few.
If you've booked your trip and are making dining reservations either online or via the phone, make sure you have your Disney vacation reservation number because they will need this to book your dining.

When you begin vacation planning and see all the opportunities for various places you can book your travel, be careful and do your homework. I've noticed that some places you can book online are promoting free transportation to Disney resorts when you stay on-site in Walt Disney World. While it might seem a nice inclusion, this is something offered free by Disney to anyone who books a Disney vacation. It's not a promotion, it's a service that has been in effect for quite some time. But you may have to book this service on your own if you don't already have your flights booked.
I've also seen "no booking fees" and "no cancellation fees" being promoted. Be especially careful of this because when you book an airline ticket, there are cancellation fees! The airlines charge from $150 and up to change a reservation plus the cost difference in the ticket you want to change to. Most airlines now charge for luggage also. Except for Southwest Airlines, all other carriers charge from $15 to $25 per checked bag. And you have to pay that price each way for your luggage. Some airlines have a discount for pre-paying for your luggage online prior to departure.
Another caution about booking airline tickets online is to make sure when you enter your name, it is exactly how it appears on your driver's license or passport. If not, you may not get on that flight.
New TSA security measures also require you to provide your birth date and gender. This is so that regular passengers don't get confused with those on the government's "Do Not Fly" list.
While the Internet is a great resource for vacation planning, I've had quite a few people recently come in and tell me that it was too confusing to book their travel online.