For the first two trips I took to Europe, I only took one carry-on bag and another bag that I carried my computer and other travel essential items in, I didn't worry about losing any luggage because nothing was checked. For this trip, because I would be going to school for two weeks in Rome and I wasn't sure exactly what text books I would need, I packed two bags and checked them. I did not follow my own rule and pack extra clothes and toiletry items in each bag and as a result, had to buy some extra stuff I really didn't need for that first night. Lesson--Always pack at least one change of clothes and a toothbrush in your second bag in case your main bag gets lost.
I could have packed less. It's so hard to really predict the weather for the area you'll be traveling to and I thought I packed as light as I possibly could at the time but I probably could have left some of my long sleeved shirts out of the mix and lightened my load a bit. I did use my warmer clothes later while I was in Rome. I was glad I packed my light jacket because I used it quite a bit in Rome also, but I never once had to pull out the jacket or long-sleeves in Madrid. I could have purchased a cheap hoodie in Rome that would have doubled as a souvenir and worked as another layer to keep me warm if the weather turned colder. Lesson--Pack less and consider purchasing a less expensive equivalent to some of the clothing you might need, such as a hooded jacket or long-sleeved t-shirts.
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