Don't have anything really much to add today, but I wanted to put something up. I've been starting to think about something to run for the upcoming Tomb of Annihilation release. We have talked about islands and sea-going adventures for some time, and this provides a stimulus to develop them.
I've started a quick encounter, just to introduce some of the aspects. I think that its important to look at trade between islands as similar to trade between towns on the mainland. The sea routes then become the roads connecting the island settlements. Finding reasons to stop at islands is similar to anything on the road - somewhere to spend the night, find fresh water, make repairs, trade with natives or a small village, etc.
Once you start having reasons to be on the sea, and putting in at the islands, it is easier to build an encounter from there.
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