As for the sailing resume, look up ed-hamilton.com, a charter broker company. I have seen many recommendations for them and am starting to use them as I set up my first charter. They have an option to complete a sailing resume and they get back to you with the biggest they would recommend. They responded to me.
Another option to consider is to charter the boat but get a captain for at least a few days. It sounds like you will have little trouble getting a boat but including a captain is at the very least a safety factor. Can also consider it a week long sailing lesson.