By any seasoned traveler's standards, I suck at packing. There simply isn't any other way to say it. It doesn't matter if I plan for weeks or shove things into a bag the night before. I will inevitably over-pack and have an absurd abundance of clothing, shoes, accessories, and underwear in proportion to the length of my stay.
My boyfriend goes by the rule, "pack as much as you can carry"-
which is great since all my luggage has wheels or he ends up carrying it
for me [Editor's note: Josh, if you are reading this I totally appreciate it and thank you]. I on the other hand justify my packing "skillz" by proclaiming "it's better to have too many options than not enough." Except now that it costs a million dollars to check a bag, my motto is proving to be a bit flawed.
I spent last week in Key West, Florida. Before I left, I made an honest attempt at narrowing down a practical list of necessities and accessories for someone taking a similar vacation. As expected, I failed miserably and wore maybe 25% of the items I actually brought. So it goes without saying, this is simply a guide intended to help streamline others that subscribe to my theory of bringing everything but the kitchen sink (keeping under 50 lbs of course). And hoping your boyfriend will carry it.