by island511 » Dec 1, 2014 My girlfriend and I are going on vacation to a tropical-type destination in two weeks. I am considering proposing while we are vacation. My biggest reason for hesitation is the risks of traveling with a $60k ring. Naturally, I would keep the ring in my carry-on. Does anyone have a good story or a bad story about such a proposal? Should I be worried or am I making a big deal of nothing? Thanks!