Okay. I am planning on bringing two bags to Disney. One full of clothes and another full of food for the week. Out of the two bags, the smaller one fits inside the bigger one. Im flying Delta after May 1 and I would be charged $25 for a second bag. I have thought about shipping a box down to our resort but if this works I won't have to. Here's My question; If I check two bags (1 free, 1 for $25) on the way down, can I put my smaller bag inside my bigger bag and check only one bag on the way back? I figure shipping 1 or 2 boxes to FL from MA is going to be more expensive than the $25 second checked bag fee. Anyone know if this is allowed? thanks so much!