Been reading along for days, and while I'm not speaking from experience ('cause I don't have any!) I thought I would encapsulate for the benefit of others (and my future self).
Why is this a bad idea? Let me count the ways...
1. It's against the rules of the road.
2. If something goes wrong guess who gets hurt
3. As mentioned, big ships like this have escorts, in this case a tug and a pilot boat, strategically positioned such that one is always hidden - run into one of them and the results are the same.
4. Your in a fricken sailboat!
5. Big ships block wind – what if you lost wind as you were crossing the bow – even if the ship missed you there's always the pilot boat.
6. I'm guessing the big ship pilots look at us the same way we look at that those unyielding fools in motorboats – I really hate to get lumped in with those guys.
7. Stupid is as stupid does.
8. Did I mention your in a fricken sailboat!
9. Farewell and adieu to you, Spanish Ladies, Farewell and adieu to you, ladies of Spain.
10. Neither the old spice guy, the most interesting man in the world, nor Chuck Norris would even do something like that - well, Chuck might, but then, your no Chuck Norris.