Most of the Carib that I have sailed was a snooze.
Getting there was a hassle 630nm+ and the stream to Bermuda, then about 900 easy miles.
From FL its a bore , running from island to island when the wind gets flat , the Thornless Path.
Once there its mostly a day trip between islands , eyeball navigation.
Sure between the islands , going N or S the wind started in Portugal and is 15K mostly to 25K , Christmas Winds , and on the beam , sail does better than power.
But with a bit of speed the waves can be taken partly ahead , so distance is traded for comfort.
Behind many of the islands , the wind is almost calm, although will become a tailwind , then a headwind as you progress.
Mostly the wind is sun driven so early AM will frequently be almost calm , power boat time!
For a gas boat the biggest hassle might be locating a dock pump with gasoline at most islands.