Originally Posted by Captainmeme
I'm sure glad the internet wasn't around when Columbus, Magellan, Shackleton or Cook was contemplating going sailing. We'd all still be living in Europe if Gore had invented it back then.
To the OP, I told my granddaughter, after she took a spill off her bike while racing downhill, "Lets go inside , lay down and stare at the ceiling. We will be safe and not get hurt." Her reply was between tears, "NO, thats boring." She got back on her bike and made it down the hill, screaming with joy the whole way.
Make sure your equipment is sound, weather is good, common sense on board and GO.
I don't think folks are saying, me included, to sell the boat and stay in your safe house and stare at the ceiling. The general consensus is to not do the first time on your "new" boat as a 100 mile + shakedown/get to know cruise alone.
Most folks are advocating a preliminary day cruise to understand the systems of the boat before making the 100+ mile trip. Most people are also advocating getting a partner or hiring a captain to do the trip with the OP.
The explorers that you mentioned all had seasoned crew for the journey and I doubt that any of them were "novice" captains and hadn't been on boat before prior to them setting off. Also, for your other example, I doubt that your granddaughter's first time on the bike was to get on and head straight down Deadman's Hill. My guess is that she went through the training wheel, then two wheel on flat stuff, before the hill attempt.