Honestly, the most complicated components of a self charter are getting out of the originating slip/marina, getting back in to your slip at end of trip, and anchoring at a crowded anchorage. The sailing is the easy part.

Below Deck has been mentioned already. I heard you can get a significant discount on the cost of the charter by agreeing to be filmed.

And when your trip airs, you can find out what the crew really thought of you and family :-)

Could make for an interesting thread - post daily reports here while on vacation... and we can compare reality vs. TV version that airs later.

We bought into a timeshare of a 44' sailboat out of Tortola - I had sailed quite a bit on the great lakes. We had use of the boat 2 weeks a year. It was an absolute joy - though we did eventually sell our share because the cost of flying was getting out of hand - and we had to start saving for kid's college.
Even as a seasoned sailor - getting on a boat is a bit of let's see 'what kind of trouble can we get into today?' - - so be prepared for adversity - though the adversity can be quite tasty.
In order to save a cruise I've had to replace an impeller, go over the sides and jury-rig a rudder at sea, and a host of other repairs.
If you charter you will either have to demonstrate you're capable OR hire a captain.
It was great.

Fill out the Moorings resume online and see what they say. It doesn’t obligate you to anything and they will tell you which boats in their fleet you are eligible to charter. And then you will know what, if anything, you need to do.