Is it good idea to visit every Caribbean island?

I am trying to see all that I can.  I have been to Curacao, Aruba, Greneda, and Bonaire.  I want to see as many of them as I can.  Very interesting.

NO, you will more than likely be killed or captured by pirates 

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DONT GO TO THE FRENCH VIRGIN ISLANDS YOU WILL GET KILLED 

The Caribbean archipelago encompasses more than 7,000 individual islands in a region of approximately 1 million square miles. There are 13 sovereign island nations and 12 dependent territories, with close political ties throughout the region to Europe and the United States. Another 10 Latin American countries include coastlines along the Caribbean.

So it might be a bit difficult to visit them all.  

ln your idea, l suggest you see perhaps Cuba, Jamaica, St Vincent and Grenadines. After those, decide if the variety of those three (or any 3 you choose) is diverse enough to see others; or very similar, too similar to continue visiting the islands.

Only visit during the season without hurricanes

And enjoy seeing all of them. Good luck

Watch out for pirates. 

its not like its a pair of breasts