Maritime Month: The island-hopping campaign

So, as I plan the maritime campaign, I need to find myself an at-sea setting. I've already decided that there is an island-rich part of the map, more or less analogous to our world's Caribbean or Polynesia, just off the existing map to the east, so it's time to map that. But I don't want to make it too defined.

The advantage of the island setup is that it's good for the kind of quasi-episodic structure my campaign basically follows -- any given island is good for a little self-contained session or three, and I can include the larger archipelago in the ongoing political development of the campaign.

I think I have three options:

• Make even the position of islands on the map random until they're discovered. I think this might be too random for me; I would not like the players to feel like they were wandering entirely at whim. 
• Plan the position of the islands, but determine what's on them randomly as players get within their rumour-radius. By rumour radius, I mean that each island shouldn't exist in some kind of fog -- if it has contact with neighbouring islands, the people there will have heard of it. Not that what they have heard will necessarily be very accurate. Consider this excerpt from a letter by Christopher Columbus (although of course Columbus might in turn be garbling what his people heard): 

Thus I have found no monsters, nor had a report of any, except in an island "Carib," which is the second at the coming into the Indies, and which is inhabited by people who are regarded in all the islands as very fierce and who eat human flesh. They have many canoes with which they range through all the islands of India and pillage and take whatever they can. They are no more malformed than are the others, except that they have the custom of wearing their hair long like women, and they use bows and arrows of the same cane stems, with a small piece of wood at end, owing to their lack of iron which they do not possess. They are ferocious among these other people who are cowardly to an excessive degree, but I make no more account of them than of the rest. These are they who have intercourse with the women of "Matini-no," which is the first island met on the way from Spain to the Indies, in which there is not a man. These women engage in no feminine occupation, but use bows and arrows of cane, like those already mentioned, and they arm and protect themselves with plates of copper, of which they have much.

In another island, which they assure me is larger than Espanola, the people have no hair. In it there is incalculable gold, and from it and from the other islands I bring with me Indians as evidence.

•  (In the above case, I suspect I will develop a tag system a la Stars Without Number and its related games and use that to generate basic island stuff. Should be no problem.)
• The final option is to generate everything in advance, and I'm way too lazy for that option. 

So I guess that comes down on the side of creating a tag system. I can almost certainly swipe the hell out of the combined Sine Nomine games to create the randomiser, because I'm that lazy.