My sister is planning her first ever Disney vacation, so I have extra motivation for really getting into the nitty-gritty of talking out how I do my planning. I'm going to focus on Disney World planning first, and then after our trip in April (taking you through all the steps) I'll elaborate more on general vacation planning on the cheap.
First thing's first - deciding when to go and where to stay. There are some great resources out there that give some insight as to when is the best time to visit. Of course, personal vacation days and school schedules may dictate exactly when you can go. However, if you have any sort of decision to make (say, 2 or 3 weeks to decide between) then it's good to do a little research.
There are three major components to deciding on the best time to go.
Cost - Most hotels/resorts charge different prices based on the busy season or slow season. Holidays are typically more expensive as is summer vacation.
Crowds - This sort of coincides with the cost section. Most vacation destinations are going to be more crowded around holidays because people have more time off work, and kids have more time off school. Of course any place, not just Disney, is going to capitalize on it and raise prices then. Because Disney is a very heavy family-friendly destination, any school holidays are going to be pretty busy. (However, realize that it's not only for kids - my husband and I have had an amazing adults-only time at Disney... we'll touch on that later). Christmastime (last two weeks of December, 1st week of January), Spring break (Mid March into the week after Easter) and Summertime are very busy at Disney. Smaller holidays like Memorial Day, Presidents Day, etc. are more popular with the locals for a quick weekend trip and very often you see a 10 out of 10 crowd levels on those days. More crowds makes for less comfortable touring... longer waits and lines, harder to get meal reservations, etc.
Weather - I'm a primadonna, so this is really important to me. More laid back people might be able to handle the extreme heat and humidity of Florida summers (over 100*F), but it's just not worth it to me. Florida summers are H-O-T.
Here are some great links to read up on to help you with your decision:
Easy Walt Disney World - Best Dates (scroll down to where it says Introduction)
MouseSavers.com - Guide to Best Value (a great read if you're priority is saving money)
Based on all of the factors above, we have personnaly decided that the last week of April into the 1st week of May is our most favorite time to visit. About 2 weeks after Easter, the crowds go back to work and school and drop of dramatically. We look at 4's and 5's (on a scale of 1-10, 10 being the most crowded). It's "Regular" season as far as pricing - not value, which is a bummer, but it's also not Summer or Holiday pricing which is higher. The weather is one word - A-MAZ-ING. This is what seals the deal for us. We trade the fact that prices are a bit higher than "value" season, because we get the low-moderate crowds and the great weather.
*I am told the same variables come into play for October in Orlando - except for Columbus day weekend which is huge for the locals - it's nice weather and low to moderate crowds.
Also, Disney runs various promotions throughout the year that will affect your price. The best way to find these available promotions are through the Walt Disney Website. Also, for your reference when planning - here are some historical discounts that Disney has set out.
So it's best to take all these variables into account before making your decision.
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