Welcome, Boatwidow! As most will comment, the decision to enter a charter program is not generally a good or bad idea. It's a personal one. It will help the group to better understand why you think it's a great idea and too good to be true. How much time per year will you spend sailing? What are your longer term sailing plans 3-4+ years down the line. Why are you excited about the idea? Again welcome to TTOL!