I don't have any personal experience with Trinidad & Tobago, but I've just got back from kiting in Peru. While I was there, I met a Venezuelan guy, Freddy Vargas, who will be running kite camps in Tobago in January and February. https://www.facebook.com/pages/Kite-Surf-Tobago/471808979545766
I can certainly vouch for Freddy - one of the coolest, most helpful guys you're ever likely to meet. I had some absolutely awesome experiences kiting with him. His passion is the waves, so if that is what you're looking for, you couldn't go wrong hooking up with him. But I believe there are plenty of flat water options, too.
Freddy certainly had some great things to say about Tobago and rates it pretty highly. I'm sure you'll have a great time.