My boys are experienced travelers. They have flown to Disney World every year since my oldest was five and the little guy was 21 months old (they are now nine and six). We always fly to Orlando out of Providence, RI, so it is a short flight for us (about two and a half hours or so), but this is the second year in a row that we have flown across the country to San Diego (which is where I am right now). That is about a six hour flight from Boston, so it’s almost double the amount of time on an airplane than what they are used to.
They are generally really good about entertaining themselves, but you never know when one of them is going to get bored, so for long flights, I always bring a carry on bag filled with things to keep them busy.
As you can see it’s filled with puzzle books, Mad Libs, mazes, Where’s Waldo books and most importantly – snacks! I also make sure I have sharpened pencils and a pencil sharpener so that they can actually do the Mad Libs, puzzles and mazes. I make sure to charge their 3DS’s and Kindle Fires the night before so that they are fully charged before we leave and that way they should last for most of the time we are up in the air.