Having lived and worked in the Caribbean (as a SAR pilot) for several decades I can tell you that the Caribbean Sea is no joke and most of the year there is a very small window in which you can cross. Other than that the seas are extremely rough. Along the coast of Venezuela you will find a very short, but high wave pattern most of the time. In the middle of the Caribbean Sea there is a long swell from one direction and on top of that a different wave pattern usually 70 to 90 degrees off and over that you have the wind pattern. Wind in the Caribbean usually is from the direction 80 - 120 degrees with 15 - 20 kts, gusting 25 kts. (weather forecast 99 % of the time).
That is roughly what you will encounter most of the year. In September we are in de doll drums and that means almost no wind and calmer seas, however...........that is also the middle of the hurricane season, a time when you don't want to be in the Caribbean unless you are in the area of Bonaire, Curacao and Aruba, which are outside of the hurricane belt.
Coming to the ABC islands via Trinidad is an option, however.........you will also need to go back one day and going East is absolutely not an option. That would mean you would have to go West, direction Colombia, Panama etc, but you will encounter extremely rough seas between Curacao / Aruba and Venezuela. Reason for this is that the waves, coming from the East, hit the Venezuealan coast and are being bounced back.
Behind the islands, the West side, the waters are usually calm, but you will have to stay within 1 or 2 miles off the coast. Venture out any further and you will be again in the strong winds and therefore rough seas. And of course, going from one island to another means you will need to expose yourself to the weather between the islands (lots of wind and rough seas).
Mexico on the other hand is also not free of hurricanes, so be aware of that.
To be honest, I don't think the Caribbean Sea is something for a 30' motor boat without stabilization. Even with my 49' stabilized boat it would not be fun. Passages are long and rough. Several spots are of course nice to go to, such as BVI's or Turks and Caicos islands, but in order to get there you will be experiencing very unpleasant seas.
And to top it off, almost all the islands are extremely criminal, which means don't be surprised if you get robbed or you find your boat looted, dinghy with outboard stolen etc.
It all sounds very negative, but it is better to know what reality is all about instead of expecting a fairy tale experience.