We have already got our plane tickets from Australia to NY and back and have booked our accommodation at WDW (which I think can all be changed) but we have not booked from NY to Orlando return and we have not got our NY accommodation yet. In Sept/Oct we are meeting up with friends for the last week in October and I am celebrating my 40th that is in November, so am planning on a cake and Grand 1 Yacht for my little 40th party. The thing is my son's school holidays are only two weeks long. So I will be taking him out of school for 4 days BEFORE school breaks up. Then when they go back, its the Tuesday 5th October and he won't go back to school until Friday 15th October, so 10 days later (but almost two school weeks), thats 10 school days late. So he will miss a total of 12 school days (which is 3/4s of the way through our school year) by going in Sept/Oct. Now the school frowns upon taking kids out of school outside of school holidays for holidays but many people do, but Im not sure for that long, but I am feeling a little guilty. He is in Year 5 now so they miss a lot more work than in the younger grades. In June/July they get 4 weeks holiday almost (June/July is mid school year for us in Australia. Our school year runs from end of January to beginning of December with Dec/Jan being our big summer holiday) So if we went in June/July he would only miss about 4 school days mid year. Now comes the poll. should we keep 3 weeks 9/21/10 to 10/12/10 where we take my son out of school for 12 school days, meet up with our friends and celebrate my 40th close to the birthday and maybe have lower crowd levels and Hallloween party or change to 3 weeks 06/22/10 to 07/13/10 where my son won't miss so much school, but our friends won't be there and it's a long way from my birthday (4 months) and not having friends won't really have a birthday party. Are the crowds just crazy in June/July????, and the weather, how is that? We live in the tropics so an average day for us is 86. Would love to hear opinions on the best time to go, I really don't know much about June/July what you would do, the crowds in June/July compared to Sept/Oct and from any parents about taking their child out of school for that long. What would you all do?