My perspective is that of a decades long sailor but a first time charterer and visitor to the BVI. Everyone has to start somewhere right? And it seems near universally accepted that there is no better place for that than the BVI. I know that, after years of talking about it, we (my wife and kids and I) never would have considered this cruise if we would have had to hire a pro skipper for the duration. Just not our style (or budget).

The checkout sail seems like a reasonable way to vet first timers for who is stretching the truth on their experience. I was embarrassingly honest on my resume. In addition to my history of sailing skiffs, beach cats, and then pocket-cruiser trimarans, but no large boats, I put down that I had a marine claim last year. Bonehead mistake, one made out of being overly-familiar with a place and situation, eventually s*** happens sometimes. Well it did to me. Unfortunately it was the year before my first bareboat charter and I had to put it on my sailing resume! But there is a paper trail and these documents have legal force right? I.e. when charterers lie and something happens, the charter and/or insurance company have some recourse? Anyway, that probably sealed the deal on "it's a checkout cruise for you!" lol, but I have no problem with, and am actually looking forward to picking up a few pointers and proving we are up to it.

So "there but for the grace of god go I", but I can't imagine making some of these mistakes you hear about where bareboats end up on the reefs or tied to channel buoys. That sounds like total incompetence, or arrogance/disrespect for the situation, operating someone else's boat drunk being just one example of that. Seems like a charter company ought to be able to identify those types after a couple of hours on the water together. I know I'm paying an extra $225 plus gratuity to prove that I'm not in over my head AND I'm taking this very seriously.