My vacation rules: try new things, take lots of naps, turn off my phone and computer, stay active—and capture moments on film.
I was a terrible packer for years until I started typing up an insanely detailed list. I separate it all into categories (like fashion, accessories, technology, miscellaneous, etc.), print it out and check things off as I pack them.
I always bring a tote to carry essentials. Inside: a silk scarf, a hat, sunglasses, Advanced Night Repair, magazines, my iPad, band-aids, lip gloss and a camera.
I try and put together outfits before I leave so that I can figure out the pieces that will be most versatile and those that I'll never reach for.