November/December is early in our season but you can usually score wind.
What islands are you thinking of? I can offer some advice on where to stay on a bunch of islands but take to long to list them all here.
*LIAT is a local airline that flies most of the islands up and down the chain ... not the cheapest option
*L'Xpress is a ferry service that connects guadeloupe/dominica/martinique and St Lucia.
*St Vincent has its own fast ferry service from the mainland to some of the larger grenadines islands
*Crewing on a yacht is another cool way to travel down island.
*you could join us for a trip and do it in luxury style.
4 to 5 weeks you could do all the islands from Dominican Republic to Tobago.
Top spots on my list would include,
Grenadines (Mayreau/Union/Tobago Cays)
On my website i have some cool pics/weather info for the islands and guide to spots in the Grenadines (the site will be updated by the end of the month with even more info!!)
We have been operating kite/surf charters in the islands since 2003.
http://web.mac.com/caribbeankitesurfari ... lcome.html
our blog is always updated with cool stuff too ... check our latest video on there.
If you want more info on places to stay / to go or spots just send me PM and i can probably help.