What we do - we fly March/April from NY.
Wear our jeans to WDW (pack shorts in our carry ons).
Wear one pair of sneakers, pack one extra pair of sneakers per person in the suitcases.
Wear our sweat shirt /light jacket to WDW (planes can get chilly).
Pack 7 sets of shorts/t-shirts/undies/socks
Pack 2 bathing suits per person
DW & DD pack
Crocs. DH & DS wear their sneakers to the pool (it's a guy thing. I guess)
We pack an old set of sheets to use with the areo bed below.
We pack extra zip-locks & labels for the suitcases trip home. Plus we have our intinerary printed on paper which is placed in all our suitcases.
Pack some toiletries in plastic bags in the suitcase. We carry-on the plane hairbrushes, tooth brushes, glasses & sun glasses & contact lenses.
We also carry-on our camera's, iPods and thinkpad.
We take and areo bed (cheap one $17 from
Walmart) also as a carry-on.
Each person has one carry -on plus a 'purse'.
So DH has a very small bag (he get the hairbrushes & tooth brushes) and his thinkpad.
DW (me) gets her purse (money, tickets, ADR's, receipts, & all eyeglass wear)
and the areo-bed.
DS & DD get a small nylon back pack - Nike brand - found in shoe stores and sporting good shops. They are very light to carry around. They pack their own sunglasses, split up our shorts between them, camera's & iPods.
I also pack another Nike brand bag with the aero bed case (not large - will fit under the plane seat) to place our jeans if we change at WDW. Plus I pack a large plastic bag to store our jackets /sweat shirts.
We fly JetBlue and they have TV's at each seat to occupy us if we are not napping.
We mail down (UPS) in a box: disposable plates, cups, bowls, utensils, zip lock bags, dry snacks, gum (not sold in WDW), boxes of cereal, garbage bags, and what ever else we want to snack on in the room.
We order from the Disney Florist the fruit basket to have fruit in the room.
Sorry if I rambled. I hope the above was not to redundant and maybe was helpful.