First, forget the notion that there are safe "hurricane holes" out there. After you and a couple of dozen other boats have set your gear and snuggle down to wait for the weather to deteriorate, all the local boats, cargo, fishing, tour, etc. will rush in at the last moment and drop some anchors
. The crew will often leave the boats and you will be looking for another anchorage pretty late in the game.
We spent this hurricane season in Grenada and it's a blast. Hundreds of boats, lots to do, planned events (like 1/2 price pizza nights) or not, hiking trails etc. and overall, it's pretty inexpensive.
Should a hurricane threaten Grenada (it happens a few times a century), Trinidad is only 80 miles away and they've never had a hurricane, I believe.
Both Grenada and Trinidad are considered to be hurricane safe by most insurance companies.
Dockside is not generally a safe place to be in any storm beyond low cat 1; many will give you the boot anyway.