The best cruising guide i have ever read for the area is "A Cruising Guide to The Caribbean and the Bahamas" by Jerrems Hart and William Stone in 1979. They used both sail and trawlers. The Venezuelan and Columbian coast can be very unforgiving once you are out of the lee of the ABC Islands and the Margarita group. 12-20' seas are not unusual. I have gone to Aruba every April for the last 30 years and generally will charter for a few days. the wind blows at a steady 20 kts so it can be a wet ride. The trip through the Bahamas is great but the run from the Turks and Caicos to Puerto Rico is a long open water ( 450 miles) run. Once you make the Virgins you will never be out of sight of land all the way to Trinidad. Then you have a 500 mile open water run to Bonnaire. you don't want to go anywhere near Venezuela. Very unsafe for gringos.
I've done a lot of pieces of this trip over the years but never the whole thing. Have never been to the Central American coast.
John