We have always chartered in early June. What can I expect to be different if we chartered in late Oct or early Nov?
June charters were SE winds 12-20 scattered rain, everything open, not too crowded (mooring balls available), temps in the 80's.

We've chartered twice around the 2-3rd week of November. Weather was great, mooring fields not crowded, everything open. I think it's a great time to go.

I would agree with CottageGirl. We are chartering the last week of Oct. This will be our third charter out of ten during Oct/Nov. and have really enjoyed the experience. Activity levels grow as your progress into Nov.

Only thing I can say is that it can be very buggy - have been down for the last three Cat Fights and the bugs were BAD all three times. Going down second week of November but land-based for a few days.

We've been nearly every year in either Oct or Nov. Always had great trips.

Is one island more "buggy" than the others?

Bugs, especially mosquitos, are more prevalent when it's rainy and in low-lying areas without a breeze. You will tend to get a lot of bugs a couple weeks after heavy rains, and Oct./Nov. statistically is the rainiest time of year in the BVI.

Mosquitos don't fly well against the wind, so an elevated property with good breezes is less likely to be buggy. Conversely, a low-lying property with a lot of brush around will be buggy. So no island is buggier, per se, but avoid a damp, low-lying area protected from prevailing wind.

We have generally gone in late March or early April but last year we left home on Thanksgiving Day. For all the reasons other folks have noted, we are going again this year on Thanksgiving. We did not however encounter any bugs but we do tend to anchor or moor away from shore and/or in a spot where there is a breeze. Many times the mooring balls further from shore are the last to go which works well for us. Keep in mind you are looking at the tail end of hurricane season.

We had several rainy trips in October including an encounter with Hurricane Omar in 2008. We have since moved our trips to late November/early December. Weather is great, water is warm and not crowded.

We usually go starting Halloween/Cat Fight weekend....and have had a few rainy days each trip...but some beauties as well.

We have been down for at least 5 or 6 Novembers. Generally very pleasant weather with 1 exception where we had a solid week of heavy rain.

Our preferred dates are in May but we've done September and October and early November. We managed to catch a hurricane that passed about 75 miles to the south in September, our October (our first time) seemed to be the rainiest time and a little hotter and muggy. December was great except we did have to deal with some northern swell. Except for May all of these are an N of 1 - so YMMV - but if we can we'll take the spring months for fewer crowds, better rates and the best chance of great weather. But we'll take it anytime we can get it.