For most voyaging purposes . a sailboat in most any size has a better chance than most "trawlers".
If you are willing to take a modest RISK, most any fully found reasonable motor boat will cross the Atlantic . Single deck only , no 3 -4 stories tall with oxygen tent on top.
Range will be a problem , but 50G drums or a bladder will add the extra few hundred gal needed.
Sadly most "trawlers " do not have the scantlings , robustness , systems or gear aboard for true ocean passages.
The reason is a cruiser will have far less space than a roomaran coastal or dockside queen.
Costing usually 300% more for an ocean ready boat , price enough to assure that 99% of the boats are coasts and bays only.
That understood simply getting to the Carib can be done either of 2 ways. The along shore run past Hispanolia has only 150-180 miles of open ocean , the Mona Passage.
Many folks , sail and power , will wait for great weather and dash across. Once in PR
, its a lark to South America.
An Atlantic passage can be done by crossing in the Horse Lats, where the old sailing ships had trouble with 5K winds , the marine motorist will find nice but rolly conditions.
Carib ? no sweat , Passage to Euroland , courage and planning.