Our boat Is headed south for Hurricane season in August. My plan was to fly down to Grenada on October 2nd. Spend 11 days sailing it to St. Vincent where I'd hop off and fly home. Captain and crew would continue it back north to STT to meet a late October charter.
Anyone have any insight on this route? I see from minimal investigation that the preferred route is to go from North to south (the opposite of what I am talking about doing) but since the boat is going to be heading north, looking at doing this then.
Is that sail going to be a miserable one against the trade winds? Thoughts on benefits of doing south route vs. mine? or is it irrelevant?
Thanks!!!

In the winter, the prevailing wind is typically east to northeast. In the summer time is is east to southeast. I'd give it a try. You may be close hauled or have to motor a bit, especially in the lee of Grenada. With 11 days you have plenty of time to get to SVG. You could motor from St. George's to Blue Lagoon in a bit more than 12 hours. In the winter, this would be a slog..

You pretty much always have to sail up wind when you are in the lee of Grenada (no mater the time of year I think) as the winds whips around the top of the island. But don't imagine you will spend much time sailing up the cost of Grenada and want to spend more time on Cariacou and in the Grenadines. I have only made it as far as TBC but with 11 days and a one way trip you should have lots of options and can make your way leisurely north. The passage from George Town to Carriacou can be rough but after that you can sail in the lee of most islands - a stop at la ronde island is a nice break. Mystique may be a headache to get too and the passage to Bequia and then to St Vincent may not be fun either.

you will be fine and sounds like a great trip. .. sigh I miss sailing! I miss talking about sailing!