I'm a backpack carryon kind of traveler but I love to make packing list and I loved seeing yours (thank you for sharing), especially the medical kit. I get motion sickness, and I pack mostly everything you have on your list except a thermometer. The infirmary on the ship is very expensive so I like to make sure I have everything just in case. Nothing worse than allergies bringing me down on vacation. Also, even though people say you can just buy what you need when you get there, I like to have the brand of item I want - if that makes sense. example, I'm picky about my ingredients in my SPF, so it's easier for me to bring exactly what I want then settle for something at the closest CVS or something. Plus I want to spend my time exploring the destination rather than shopping for personal toiletries. Can I also add, I just added a travel size Poo-pourri to my packing list and I've very excited about it.
The category that always ruins my packing is the rain gear. I packed a rain jacket, rain boots, and umbrella on a cruise one time during hurricane season and of course, it didn't rain at all.
My sister and I travel a lot together and we love to plan early. And when you find someone who is just as excited about your vacation as you are, even if it's a year or a month away, it is just that much more fun. We like to use Travefy to plan our trips together.
Since you mentioned a Western Caribbean destination, you might to consider an underwater camera. I like to bring my husband's go pro and waterproof case for snorkeling. Also, maybe a small tripod if it's just you two? i guess it depends on your camera. I have an canon with a flip screen that I love.
also, what's a lock bag? my sister told me to pack a lock on our next trip. wondering if this is a good sub b/c a lock is super heavy.
i would be interested in knowing what's in the makeup cube too. care to share?