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Never have and honestly I got goosebumps just reading the end of your comment!! I have just recently started to get more comfortable on my boat during launching and docking but as soon as I see the sky darken a bit I am headed to the dock before anyone else even budges to avoid this nightmare! I am so dreading a scenario like the one you depicted but I thought if something like that happened what would I do. I have no clue! Throw the anchor and swim for shore LOL!
Don't worry about the enevidable, as you become a more seasoned boater you will experience unfavorable weather, being prepared and safety concious are valuable qualities keep them. The same rule apply as discussed with the dock...DO NOT PANIC, be aware of your environment, take control of the situation and use healthy doses of the not so common, Common Sense. Remember many others have been in similar or worse situations but made solid timely decisions and arrived home with all passengers and equipment a little shaken but unhurt/undamaged. You do not need dark clouds for a sudden increase in wind on a clear day, the clouds don't make the waves the wind does(me too). You did mention anchoring the boat and swimming, if you had a mechanical failure along with the unfavorable weather this is definately an option, considering you have a mooring anchor or one heavy enough to stop your boat from washing up on the shore, and all of your passengers are capable of swimming back etc. The dark clouds carry a more unpredictable inherent danger called lightning...really hard to outrun when you are the best ground around truly and electrifying experience I have not had the displeasure of encountering(came close a few times). You cannot predict the weather, I have yet to see a weatherman do it consistantly (no offence) point is you can dock on lakes and go golfing, if you are on the 14th hole when the weather rolls in you are going to have you work cut out for you...even tougher if you eagled the last hole. Thinking outside the box is a good thing, if there is a cross wind and white caps pushing your trailer sideways, you may need your anchor more on your trailer than you do on your boat, and your approach will be faster but the resting place will be the same. Communication, and Control in extreme situations will help to guide you through don't fear the enevidable face it, and prepare for it... you will be fine !