It's all in the clothes you have. I buy clothes that "fold small" and I really don't care too much about wrinkling as you can always iron or spray the wrinkles out with wrinkle releaser (Downey makes it) Limit your shoes to this - beach shoes, walking shoes (sneakers) I usually wear the sneakers cause they take up the most show room - and 2 pairs dress shoes one black one neutral. I wear a designer track suit on the flilght, which solves the light jacket dilemma and does not need to be packed. I pack 3 pairs of shorts, 3 bathing suits, 2 tank tops, 1 pair dressy black pants, 2 dresses etc...I pick all clothes to mix and match and bring extra shirts - sleeveless or short sleeves take up very little roon and fold into a small square. Put the shoes in the bottom and fill around them tieh small items such as bathingsuits, underwear etc till you have a flst foundation then fold the clothes and layer them so there is not a bulge in the middle. and voila....your done. i do pack my husbands shirts in a spacesaver bag. and use ziplocks for toiletries ofr wet things. I pack all this in 4 carry ons 2 each for DH and myself. It can be done!