In the last 5 years, many insurance companies have relaxed their policies and allowed boats to be inside the "hurricane box" during hurricane season with only an increased deductible (double) and no increase in rates. So many cruisers have opted to stay in the northern part of the islands (St. Lucia all the way up to Puerto Rico). I would guess the numbers are at least 50% (and probably more) of the cruising boats that are in the "hurricane box" during hurricane season.

Trinidad is outside the "hurricane box" as is the southern part of Grenada. Venezuela is not an option for obvious reasons (safety and security). The ABC islands are also fine during hurricane season as is Panama and parts of Colombia, if you wish to exit the Eastern Caribbean.

I would expect all of this may change with the massive destruction caused by Irma this season. It may not be possible to stay inside the "hurricane box" and still be insured post Irma for many years.