We're looking into the plausibility of cruising on our motor yacht from Columbia to Trinidad and Tobago. Our two major concerns are pirates and security off the coast of Venezuela, and the head on pounding of wind and waves traveling west to east. Is there member who has done this route and can share their adventure?
Not sure where your eventual destination is or your cruising plans, but the trip east sounds hateful and that is without the possibility of pirates. And, unless you are the quite adventurous type, there is limited opportunity for safe, comfortable and leisurely cruising until you get to T&T.
I would suggest considering, if looking for great cruising in interesting areas going N to Honduras (the Bay Islands) and (perhaps) Guatemala (the Rio Dulce), then Belize and on to Mexico and then around to Cuba. Lots of possibilities from there.
This route would have you with the wind and seas generally on the beam and in predictable countries that welcome cruisers and in wonderful cruising grounds: to me, far more interesting than the eastern Carib with all its boats, tourists, etc. Belize and Honduras have superb Maya ruins that rival anything seen in Egypt for spectacular-ness, atolls for diving. Belize has jungle and all have interesting history.
You would also start to pick up the Gulf Stream which helps as you go N and get around the corner above Cuba.
Write if you have questions and want more information on this route.
My best, Dick Stevenson, s/v Alchemy