I have never played Elder Scrolls Daggerfall but the thought of being able to own huge ships and sail around the world sounds like it would be awesome and fun. The past three games have been landlocked and I would like to be able to explore more of the world between several continents. Is there anywhere in the game's lore where the places is like the carribean or something? lots of islands and settlements where you can sail between different places? how did owning ships work in daggerfall?

Probably Summerset Isles would be a good place for such a feature. Being able to sail around the islands to ports.

Or Yokuda far to the west of Tamriel, the origional home of the Redguards, though according to lore it sank into the ocean, so perhaps a game far in the past would be necessary to properly explore it.

There's references to people trading with Yokuda. All we know is that the Redguards had to leave; it may well still be there, in some condition or other.

As for the ship, that does sound like a nice idea. Daggerfall didn't do much with it (it basically just served to make ship travel free - for which it took a long time to be cost-effective and as a place to store things), you never got to see the thing sail around, and there weren't any physical ports for it. Better technology, though, means that Bethesda can do a bit more with it if they care to put the effort in, and I'd certainly like that.

When the Empire invaded Akavir (Ionith), they island hopped on their way to the eastern continent.

I agree. One of my favorite things to do in Oblivion was to sail around the entirety of Tamriel and Summerset Isles, using the Tamriel Heightmap Project and Side's Sailing Ships mods. I would literally spent hours doing nothing but sailing. It was a wonderfully relaxing break from the frenetic combat that Elder Scrolls games are crammed with. I would love it if Bethesda implemented something like that.