India, June 15 -- I have been on 27 cruises. After that many adventures, you would think that I would have the packing thing completely figured out, and for the most part, I do now. However, it took a lot of mistakes to get here. I have shivered through formal dinners in the wrong outfit, limped back to the ship on blistered feet, stood soaking wet at a port without a rain jacket, and sat on the pool deck squinting into the sun because the hat I packed got destroyed in my luggage before the ship even left port.

All my packing mistakes taught me a lot, and every single one of them could have been fixed with one simple clothing item I had left at home. These are real mistakes I made across 27 cruises, and for each one, I am sharing the exa...