The key is to find someone who does training as a profession. That is, they have an established and organized lesson plan, a method of determining the amount of instruction you need, good communication skills and unlimited patience.
Down in Florida, Seasense and Chapman's come to mind. You could take one of their basic classes, then hire one of their instructors for advanced one on one training. My wife used SeaSense and it was great for her, and I have heard good things second hand about Chapman's. After learning the basics, you will want to go on an actual cruise with an instructor. Then do some bare boat chartering of different types and sizes of vessels. I can virtually guarantee all this will be the best money you ever spend on boating.
This process will also help you determine a) if cruising is really for you and yours (an SO should be involved somewhere along the way, especially the cruising segments) b)what you are really looking for in a boat (size, design, ergonomics, performance, cost to run, etc) c) or if you'd be better off chartering.