I skipper a Clipper yacht (not in the racing) and I often compare sailing and flying. Well, you know what they say about "Better to be down here, wishing you were up there, rather than up there and wishing you were down here"...well, that doesn't work for sailing. When you set out on any voyage by sea of any distance, the weather forecast only takes you so far and then you simply have to deal with whatever the weather throws at you because there isn't always the equivalent of a precautionary landing when things get bad. I've been much more uncomfortable at sea than I ever was in the air (although, to be fair, I have much more experience at sea). And if you embark on challenges of the type done in the Clippers, you're gonna face some pretty horrible conditions at some point. And, the kit you are using is going to get a right battering. And you can be stuck in those conditions for days or weeks if you start doing ocean crossings. And, when bits start breaking, which they will, you really do want the vessel to solider on and sustain whatever damage arises. And the Clippers do just that.
Many times I've been slogging my way across some 'orrible bit of water with waves breaking over the deck and I look up and see something like a Cessna merrily making its way overhead, knowing that he will be having tea and biscuits in the clubhouse while we are still bashing away doing 6 knots in the dark. In fact, anyone want to buy some secondhand sailing gear?