DH and I recently took a 16-day trip to Australia, and I read packing tips/advice a few months in advance, as there were a few things we needed/used frequently on our trip and didn't have/had to go through the process of ordering online, waiting for delivery, trying on, and exchanging if they didn't fit. It was also summer weather there, and winter here, so I had to go through our summer stuff and order a few things like shorts for DH since he only had one pair that fit. We also packed for 16 days in two carry-on suitcases, and two backpacks---while leaving ample room to bring back souviners/gifts for family.
Because the majority of our stuff wasn't every day winter wear I packed the suitcases the weekend before we left, and we put toiletries etc in our backpacks. I made sure all our liquids were in two small ziploc bags in a specific backpack so it was easier to get through many security checkpoints. I used the 'bundle' packing system, which involved laying all similar clothing items (i.e. Shirts:put long sleeve in neat stack and short sleeve on top, with DH's shirts below mine bc they're larger), and then rolled the stack/pile up really tight like you do with a sleeping bag. We kept the clothes in their rolls during the trip, we'd unroll the shirts in the AM, each grab one, roll it back up, and stuck the dirty ones in our dirty laundry bag. The underwear roll got unrolled when we first needed it and only got re-rolled when we packed for home bc it was more convenient---we stayed in 9 different locations and didn't want to spend a lot of time unpacking and repacking.
We took a one-night trip last week and packed in 20 minutes, which only took so long bc I couldn't find a gift we had purchased months ago that we needed to take. I have prescriptions that are filled monthly, and if I know I'm traveling when I fill the RX I do the math to figure out if I need to refill in advance/if I'll run out while traveling.
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