I'm debating whether to pay for checked luggage or to ship a box to myself at the hotel. Any comments on the pros and cons? I've never shipped a box to a hotel before. The first leg of my trip will be a flight to Miami, where my traveling companion and I will be for three nights before driving (small rental car) to WDW. (4 nights at the Dolphin.) After WDW we will fly home via Southwest, but the airline that's taking us to Miami (American) will charge $25 per checked piece of luggage. So I am thinking that for $25 or less I could ship a box to the Miami hotel and not have to hassle with checked (and possible lost) luggage at the airport. Then on the way back I would just have luggage for Southwest. (I would be including a large duffle-bag in the box, for the return luggage.) Does this seem like a good idea? What is the most economical and safe way to ship things to hotels? (Note that I would be shipping to a "business class" hotel in Miami not a WDW resort.) Any tips as to size of box, weight, carrier (UPS or USP?) etc? Thanks.