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Grenada is great for the hurricane season, I have spent the last 3 here in Grenada. You can take a break and sail up to the Grenadines and still have time to run south if something threatens.
I have done Trinidad a dozen times and really like the place. But as mentioned you have to be "big city street wise" or you can get into trouble. There are tons of wonderful tours and hikes and things to do there. Tobago on the other hand is getting rather nasty about cruising sailboats and where you can go. Lots of restrictions and bureaucratic hassles. The only problem with Trinidad is you are "stuck" in the bay/marina/anchorage you choose and really cannot sail anywhere (there are exceptions, but not many).
In Grenada there are lots of bays along the south shore; west shore; and up into the Grenadines (Carriacou, Petite St. Martinique, PSV) where you can sail without having to check out of the country.
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