1. If possible try to plan what you are doing each day. i.e. do I need to bring more casual or more dressy outfits? Do I need a bathing suit? If I'm dancing the night away (which I hope to be doing) I need to bring more swing dresses and less pencil skirts etc.
2. This sounds crazy but try to stick with outfits in three or four colors. Choose a base color like black and go from there. My choices this year are black, white, pink and grey. This limits the amount of shoes you have to bring along and enables you to mix and match if necessary.
3. Bring 'multi taskers'. i.e. Pack a black and white sun dress. You can wear it with sandals, a hat and tote-bag during the day but dress it up at night with fancy heels, a clutch, matching hair flower, patent belt and rhinestone jewelry. One less outfit to bring!
4. As far as packing goes, open your suitcase and lay down your outfits flat over it-- one on top of the other. Don't fold them. Once they are all laid down flat you'll have pant legs and sleeves hanging out over your suitcase, don't tuck them in yet. Push the flat items down to the bottom, then fold and roll your PJs, T shirts and anything else that you don't have to worry about wrinkling. Place the rolled items on top of the flat ones, THEN fold your pant legs and sleeves that are sticking out from the flat clothes on top of the rolled clothes.
5. When traveling always wear the heaviest clothes or the ones that take up the most room so you don't have to carry them. If you bring jeans, it's better to wear them. Last year I wore my crinoline through the airport and on the plane, (under the appropriate skirt of course.)