It might be a bit late to respond here, but, I've taken the same route even further in that I charter locally here in the SF bay rather than own any boat. This has afforded me the opportunity to bareboat in the Med - Croatia and Greece multiple times, the Seychelles, and Baja. I've also crashed with some cruiser friends in the Bahamas, Belize, Sardinia, and Corsica.
Now, I've finally got around to putting all this experience into a site/blog. check out my bareboating advice posts
for some of my insights and trip overviews. But, here's what comes to mind right now:
- decide the blend of sea vs land you'd like to experience. We happen to max our time at sea and don't mind cooking on board,
- take weather seriously like crusiers do. It's saved our butts a few times.
- and make sure that the water tanks are filled before leaving. There's nothing worse than finding out the first night that you have to go to port to refill even before the vacation begins.
OK, there's a lot more, but, generally, the boats are in great shape and the companies try hard to make sure you have a great time.