Yes packing for vacation is such a chore. Sometimes just doing it for yourself can drive crazy, but do it for my three kids and I gets to be such a hassle. Seven days away for four people with limited luggage is not easy. Secrets to packing I have is to roll your clothes tight and this can actually save lots of space. Of course it doesn't work well for items that need to be ironed, but then I won't wear a shirt that needs to be ironed on vacation.
The other fit on vacation I seem to have is trying to find a nice shirt to come back with to represent the trip or even give as a gift. How come most just look thrown together by the cheapest possible method and then attached to a $50 price tag? No thank you. My memories will do. However, I still search in vain. Wish me luck.