It a long trip, but can be a lot of fun.
I think you have two possible routes: (1) through the Bahamas
(or along the eastern side), down the Windward Passage
, then on a broad reach to Colombia; or (2) along the western side of the Bahamas
(but outside the Gulf Stream), westward towards Mexico
, then south to Colombia on a beam reach.
There are pros and cons to each.
The virtue of (1) is that you avoid the Gulf Stream
but the negatives are crossing the Old Bahama Channel and winding your way down the Windward Passage and the problems of those countries and having little choice for repairs
, or crew change. You can hit Jamaica
(or maybe you could hit, imo, I'd stay far away from Kingston for a while) or further south to the ABCs.
The virtue of (2) is almost the opposite of (1) but you have to contend with the Gulf Stream until you turn South off the western end of Cuba
. You'll have the Gulf Stream for a considerable length of time. And there's that BP fiasco in the Gulf.
Distances are about the same but the slower speed due to the Gulf Stream may impact the time. Given the choices (and I've done it both ways), and a well found boat and crew, I'd opt for (1) despite the tension crossing the Old Bahama Channel and the Windward Passage.
Good luck on the trip. It can be a fantastic way to get some long distance offshore sailing, some fine fishing
chances, and a real taste and smell to the Caribbean