A. What age is the right age to go?
There isn't one right answer to this question. What it depends on is whether or not you will go again. If, like me, you're going multiple times, you can take any kid of any age there. My son was just over a year old the first time he went; he napped in the stroller while one parent took our older daughter on rides (and if both parents want to go on rides, check out rider switch). At that time she was three, and the look on her face when she saw her first princess....priceless. Nowadays, at age 8, she's a bit over it. The nice thing about going multiple times as the kids age is that you'll find yourself trying out different rides and shows as they get old enough to appreciate them (or tall enough) and the experience changes every time. Of course, I recognize that not everyone is as fortunate as I am to go multiple times, so this answer really depends on your family. You want your kids to remember it (but even after going at age 7, my sister doesn't remember her trip to Disney very much). Are your kids good travelers? Do they sleep well on vacation? How well do they deal with overstimulation? Disney is an incredible place but it's also busy, noisy and exciting. This can be a lot to deal with for some kids, and sometimes being a little older will make it easier. If it's a big deal for you to go out with diaper bags and strollers, it will definitely be worth it to wait until you're out of that phase. Sometimes even just a year can make a big difference between a fun trip and a journey to melt-down city.
B. What time of year is best to go?
Obviously, when the kids are in school. September, just after school starts, is probably one of the best times to go. Even Summer break isn't bad because not a lot of people want to deal with the Florida heat. Winter break (the two weeks around Christmas/New Years) is the absolute worst time to go - you couldn't pay me to go at that time. Spring break is hit and miss, because unlike Winter Break, not every single school in North America has the same Spring Break. The week of American Thanksgiving is almost as bad as Christmas. Your absolute best bet at figuring out the best time to go is Touring Plans. Getting a membership will not only be the cheapest thing you do when you visit Disney, but the smartest. Have a look at their crowd calendar, which is on a scale of 1-10. Obviously lower numbers are better, and beware that if you do decide to go on a day when it's a 10, you will need a park reservation early on or you might not get in at all (no more last minute trips at Christmas!). I prefer days that are 6 and under, but even an 8 is comfortable with enough planning. Sometimes, shifting your vacation by just a few days can make a big differences in crowds, so I always check the crowd calendar to see what days would be optimal in the time frame I'm thinking of. We'll talk more about why Touring Plans is so awesome when we talk about Genie+ and planning your day at Disney.
Once you have decided when you are going, you'll have to decide how many days your trip will be and how many of those days will be spent at the park. It makes sense to go for 4 days, one at every park. In an ideal world, you'd go for at least 5 (spending 2 days at Magic Kingdom), taking a break in between each park day. Having a longer trip is cheaper if you're staying off site, which is what the next post is about. I will finish this post by saying that in addition to deciding on the length of the trip, know which days you'll be visiting each specific park (the crowd calendar will help you figure out which day is better for which park), which will make the rest of your planning easier. There is a ticket called Park Hopper that lets you visit more than one park in a day, but I feel it's easier to stick with one park per day (not to mention cheaper!). I would also at this point make an account at DisneyWorld. Every adult in the party will need to have their own account -you will need one if you are staying on site, to make dining reservation and Genie+ selections. You can add people to your Family and Friends list so that one person can make all the reservations for everyone, but each adult will need to have their own account.
Here are the other posts on DisneyWorld planning:
1 - When to go to Disney: what age is a good age? What time of year is good to go?
2 - Where to stay at Disney: breaking down the pros and cons of off vs. onsite
3 - Advance Dining Reservations: because hour long waits for lunch/dinner are for non-planners
4 - Genie+: getting on the rides faster
5 - What to take to Disney: including discussions about strollers, magic bands and memory maker
Updated Nov 30 2021
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