October will still let you see some winds, but you are in the high season for hurricanes (or TRSs if they don't grow up enough to get a real name) and you will need to keep an eye out for the weather
. I helped return a cat to Oyster
Pond yesterday and the entrance was pretty rough and becomes impassable in very heavy weather.
is great at your time of year, since the winds and swells that otherwise make that open anchorage uncomfortable might not be there.
St. Martin, Sint Maarten, Anguilla
and St. Barths have a lot of things for you to see. St. Kitts & Nevis
have some noteworthy sites (Brimstone Fort, for example) but the anchorages
that are comfortable have nothing ashore, and Basseterre is, in my opinion, usually untenable. So unless you really want the sailing miles, you might want to visit St. Kitts and Nevis some other trip and get more quality time in anchorages
such as Ile Fourchue, Ile Tintamarre and Anse Colombier.