So, Italy will have to wait...we've decided to find a compromise and we're going to do a self-catering trip to Turks and Caicos instead.  This way, we get a little of the beach relaxation I so badly want and a bit of exploring too. (And hopefully loads of fresh seafood!)
My (first world) problem is this:  because of scheduling and costs, we're booked to go only 3 days after getting back from 5 days in Maryland, and I'm not sure what to do about packing?  Should I pack for both trips in advance of leaving for Maryland (as a fall trip to the eastern US coast will be very different than a trip to the Carribbean!), or come home, unpack and re-pack?
What have you done when doing back to back trips?