I've just joined this site and see that you are in a similar position to myself. I have a boat (SY SKARDU) currently in Phuket, half-way around a circumnavigation from England to England. I am looking to sail across the Indian Ocean during '09, and am weighing up the options of heading down to South Africa and around the Cape, or up through the Red Sea to the Med.
I am also looking for the latest possible start date from Thailand to start heading West. From some geneal enquiries there, it seems that a lot of cruisers prepare themselves for the Westwards passage over the Christmas and New Year period, and then head off in Jan sometime, but it might be still ok to go as late as Feb. It you (or anyone else) has any further information to add to this, it would be really appreciated.
Another similarity!... is that the reason that I am trying to go as late as possible is that I also currently have to get some work (money!) under the belt before I go, and might be in the UAE from next week until about Christmas! Maybe we could meet up and discuss plans if you are also there?!
Good luck and best regards,