We're there from 10-10 (checkin) to 10-20 out of Horizons on Wavelength. We've found Oct to be nice and quiet, like we like it. However, we are scheduling our stops around the regatta's schedule. We like it when most things are closed We provision and cook on the boat more often than eating out.

Be sure to get trip insurance. We were scheduled to charter out of St. Martin in Oct 2017, which obviously didn't happen. Without insurance it would have been a very expensive non-vacation.

We've been somewhere in the Caribbean every Oct since 1990. Most of the time the weather is fine, with some showers. Once we had rain basically every day, all day. Three times we changed our trip because of hurricanes.