Planning Disney vacations have always been a lot of fun in my family. It usually begins with plotting when to go. Most of our trips have been during the summer months because we didn't want to take our teenage daughters out of school. Summers are hot in Disney, so if you can't take the heat and humidity, go during months when it's cooler in Florida, (typically November through April). We often go in August because the crowds are a little smaller since many schools in the south begin in early August. It's also a value season in Disney which means you can get a better rate staying at a Disney resort. If you have AAA, you can get an even better rate. Some people can't decide whether to stay in a resort hotel on Disney property or to stay off-site. I stay on-site which allows me to take advantage of Disney's Magical Express service. The free service to guests staying in a Disney resort, shuttles you from the airport to your resort and then back to the airport at the end of your trip. This saves you the expense of a rental car. Another great service provided by Disney is the ability (through participating airlines) to drop your luggage at your home airport and when it arrives in Orlando, is shuttled to your Disney resort and brought right to your room! So when you arrive in Orlando, you just bypass baggage claim and head to the lower level where Disney Magical Express cast members greet you and get you on the bus to your resort. The buses stop at several resorts so yours may not be the first stop, but it gives you a glimpse of other Disney resorts you may want to visit in the future.