In the sailing world we use this term in the pursuit of the best winds and/or avoidance of issues derived from big gusts. My most memorable moment of "Cloud-Hopping" occurred on an afternoon when my wife and I were out on a borrowed Catalina 22. We had sailed about 5 miles from our yacht club and were enjoying a picnic and just sort of skipping around when I noticed the clouds on the horizon to the north were getting really big, really fast. So, we pulled the main/jib and were gliding along at 7-8 knots. My love of the quiet speed, high heel and cooler temperature (July Summer Heat), caused me to ignore the possible need for reefing. Also, my wife's rain-tolerance wasn't very high as we were just learning the art of sailing and I knew a bad experience would ruin my chances of getting her back out. As the wind increased, so did our speed and tilt and I was feeling like a massive hero! Then as the storm stepped up the intensity, our forward motion declined and I began to loose steerage. The boat was nearing knockdown when my wife's eyes began to display concern. I calmly told her to put on her PFD and I fell off (not literally; sailing vernacular for changing the boats direction and thus slow down). The boat began to move toward the shore so I released all of the lines, and cranked the keel up in an attempt to slow the chaos but it was too late....I grounded. Realizing we weren't going anywhere, I kedged an anchor just in case we needed and told my wife to move below where we had a cup of coffee and rode out the storm. Approximately 20 minutes passed and so did the storm. Shaken, wet, and now concerned with possible damage, I prepared to get back underway. We did so with no further issues.
There's more to the story but I'll close with this: Lack of awareness and preparation increases our chances for things going wrong....this is true whether you're sailing, singing, living and dying. Preparation for the life you will live after you die (and you will live....somewhere) is much more crucial than the life you and I have prepared to live here on Earth. I heard a great quote from a Hatian Missionary which I will leave you with: "You're immortal until God is finished with you."