Hottest time of the year out here is usually September / October.
This year has been relatively 'cool' - it was not tooo hot in August. This might help to explain why the hurricanes were very quiet this summer, despite fairly dire warnings at the beginning of the season that we could expect to see a few humdingers in the offing.
The probability of hurricanes happening increases as the sea temps increase - summer 2004 was noticeably scorchio from early on, and the sea temps were (I think) 2 degrees above average (similarly summer 1995) - and 2004 was the year when they ran out of letters for hurricane names.......
Hurricane Ivan hit Grenada in 2004 (here is a wiki link to him -
http://en.wikipedia.org/wiki/Hurricane_Ivan ) - he was forecast to go over Barbados, and then clobber Bequia / St Vincent, but he persisted on staying south, with no veering northwards as predicted.
We were lucky - if we had winds gusting to 150 knots we would have been properly flattened.
But looking on the bright side, the previous hurricane to affect Grenada was Janet in 1955. The odds of encountering a hurricane increase as you go northwards up the island chain.
If you go sailing from (say) St Vincent in August you can expect a rain squall (or 2) every day, and maybe one day a week where it might rain all day if a tropical wave is passing through. The winds are not as steady as during the winter, but still a lot more reliable re strength and direction than around Britain.
Summer temperatures are generally cooler than the Med - its a very hot day here if the temp is 32*C.
And you might even have some anchorages to yourself - even the Tobago Cays will be looking rather sparsely populated, whereas during the winter season the Cays are a bit like a larger, tropical version of Newtown Creek re traffic.
This website about the Cays does not really do them justice -
http://www.tobagocays.com/