If we had to choose between early May, later May or early June, which would be best weather-wise for chartering a sailboat?

Early May.
**Jim

Thanks,and why would that be your choice.....?

The winds would be more reliable. Temperatures are just beginning to become warmer due to the onset of the rainy season. Later on the winds can be erratic or can die off suddenly. Later in June it is possible to get into very humid and hot weather especially if a depression is anywhere near.

**Jim