Originally posted by Alji:

Build a workbench near your boat and use your hammer on it to repair it. Always carry at least 10 wood with you when sailing so you you can hop out at any patch of dry land for more repairs. It's really weird that you could take enough damage to 'not make it to the next island' ... unless mods something something.

I have no mods installed. I play just me and a friend. But it happens to us regardless of who drives the boat or if there is only one in the boat sailing.