If you know me, you know I am an extremely organized packer for vacations. I function best when I feel fully prepared, and when I'm not lugging around a bunch of excess things. I'm so not a throw-everything-in-the-bag-the-night-before-my-flight type of person. By special request, I'm sharing how I pack.
I went to Italy for two weeks in 2017, and I literally only took a carry-on suitcase and a purse. This involved very minimal outfit re-wearing. My secret to packing: packing cubes and a PowerPoint presentation. This is so not for everyone, and I get that, but it's what helps me. (At the very least, I recommend a hand-written list to help you sort your thoughts!)
A note about packing cubes: I prefer them to have more mesh because I feel like they have a little more stretch to them.
The main takeaway: plan your outfits in advance. There's no option for "what if I feel like wearing this instead" in this method, but honestly you're so well-prepared that you don't feel like you need all of those "what if" outfits. (Disclaimer: I do allow for one or two extra just-in-case outfits; I'm not a total monster.)
I make a slide for each day of my trip, and type what's on the itinerary for that day.
Then, I add pictures of my outfits that I intend to wear. This works especially well if you've ordered a new outfit online because you can just copy and paste pictures from the website from which you ordered. Otherwise, just Google "black tank top" or "jeans," whatever the item you plan on packing may be, and copy and paste the image.
I place the outfit on the slide with the day's activities that correspond best. Repeat for each day, and you're set. You know exactly what you're wearing, you know what you're doing, and your outfit fits your activities.
When it comes to the actual packing aspect, I roll everything and put it into packing cubes coordinated by outfit, not clothing category (i.e., shirts, pants, etc.) This means that pulling things out of my suitcase is organized too- I don't have to go into multiple cubes to get a complete outfit for the day.
I do the same when traveling for family trips. An added bonus to this: seeing everything visually also helps your family look coordinated in all of your vacation photos on any given day!
For Italy, I packed a flattened duffle bag in my suitcase so that I'd have room to bring back souvenirs (read: wine and luxury purses). Another tip: be sure to check your airline for the exact weight and dimensions of their carry-on requirements. The size differs from airline to airline and it would suck to go through all the trouble of cramming things into a small bag and end up having to check it anyway!
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