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You do have to be careful when you're rolling them because if you roll carelessly, you'll get huge wrinkles that won't budge! I roll everything and then I shove the smaller things like underwear and socks into shoes to free up even more space in the suitcase. I've really had to get creative since having Maddie because we didn't want to have to pack an extra suitcase for her. It really made me re-evaluate what I could and could not live without of mine on vacation since about 1/2 of my normal suitcase contents are no longer able to go!
When we go on a cruise in a couple of months, I'm trying to challenge myself into taking just 1 big garment bag for our evening attire and our small suitcase for daily attire. The lighter we can travel the better because I'm too paranoid about giving our luggage to the porters to deliver to our room, so we'll have to lug it around the ship with us for 2 hours before our rooms are available.
My goal when I go to Chicago is to take my one big rolling suitcase, and that's it (well, other than my bag I'm taking on the train). I'm already stressing out about trying to fit everything in there. Maybe I should practice rolling some clothes so I can get it down before my trip!
Allison, wife to Aaron (9.28.02), and mommy to Aaden (6.17.08)