Bucket List # 2 - Sailing the Caribbean

Call it echoes of Captain Ron, or just the simple predilection of a beach bum, being able to spend some serious time aboard a sailboat has long been a desire of mine.  Actually, restricting it to sail boating is probably a little too much - just spending time on the ocean is great by me, but the added benefit of being able to sail around and dock wherever you like has more appeal.  I'm not picky though - I'd be happy to be aboard a power yacht, if that is what it took to make it happen.

The crazy thing is, as expensive as this sounds, this is actually well within reach.  The Moorings (www.moorings.com) offers a variety of yachting experiences, ranging from "learning to sail" trips to the fully staffed yacht charters.  While I haven't exactly figured out what the appropriate level of charter would be for me and my family, my initial take was that I could get a week long powerboat yacht charter with staff for only around $5,000.  That's total, mind you, so significantly less than my first pick (the Orient Express) which ran around $4,000 per person.

Yeah, this is pretty close to what I'm imagining.

While I probably still have to do a little research on this one, it does seem surprisingly affordable, especially for a family of four, although destination and craft type may create some different pricing points.  That said, I might have to look into this as an option in the nearer future than I had originally thought.

What I would like to know is other people's experience with this sort of thing.  If anyone out there has chartered a boat or spent any time sailing (or learning to sail), I'd be curious to hear your thoughts.