Weathers is a gamble, any time. It seems to me (and this is completely my uneducated observation) that the tender problems in Grand Cayman seem more prevalent during the spring time, but I could be nuts. Rain is a possibility any day in the caribbean. I have sailed in April once, but usually prefer the fall for the better prices. Plus the fall weather has always been great (Aprils weather was great too, for that matter). I think I've just been lucky in the weather department. My suggestion would be, and this is more based on price than weather, would be fall... Sept-Nov (cant say yet for Dec, have my first Dec sailing coming up later this year). Kids are in school, hurricane season is winding down, temps are great (not too hot), etc.
