Well lets see...
I'll make a few quick visual comments. The new boats and flags look ten-hundred times more appropriate for the map now, don't you think? Maybe consider continent unique ships (I.E. British ships don't look like those of the Spanish).
The skull and crossbones doesn't seem to quite have the same feel as the other images now. It looks almost a little too menacing. Perhaps try a different image, or create your own (if you created the boats and flags, kudos to you!)
Regarding the title, it looks alright, I'm not sure how you can improve it. There isn't a lot of room to work with. If you had more space, I'd consider making a parchment/treasure map background for the title, similar to the legend down below. And speaking of the legend background, I like the general idea of the scroll, but it may look a little too 'real' compared to the other visuals. But maybe not also!
And in the bonus legend, maybe consider a slightly different font than the one you have. It can be difficult to read sometimes. If you could find a font that was similar yet easier to read, I think that would be a plus. But if not, it really isn't that bad.
One last thing, consider making the attack routes a little more prominent, they are very pleasing to the eye, but they might blend in a little too much with the sea.
Anyways, lets take a closer look at gameplay:
I think I count 42 countries, correct?
Cuba -- 6 Countries, 4 Borders, Bonus of 4.
Bahamas -- 6 Countries, 3 Borders, Bonus of 3.
Espanola -- 4 Countries, 3 Borders, Bonus of 3.
Geeward -- 6 Countries, 4 Borders, Bonus of 4.
Mindward -- 4 Countries, 2 Borders, Bonus of 2.
Columbia -- 2 Countries, 2 Borders, Bonus of 2.
Venezuela -- 6 Countries, 3 Borders, Bonus of 3.
British -- 3 Countries, 2 Borders, Bonus of 2.
Spanish -- 5 Countries, 5 Borders, Bonus of 5.
Well lets see...a few maps have tossed around the idea of lots of little bonuses similar to this one, but this idea seems to work pretty well, though it'd be nice to see a few variations in number of countries. Adding a continent with 7 countries, and one with 5 is something to consider. I'm not sure where you would do this, as I am not too familiar with the area and the regions that make up every area.
I like the general flow of the map, maybe consider adding a few more attack routes (these won't increase the number of borders for any continent):
Holquin // Turks (Similar to the other triangle connection you have on the other side)
Or perhaps consider Holquin // Calicos (If you choose to implement more attack routes, I'd choose only one of the additional Holquin routes)
Melchor de Navarrete // Maracaibo (Unless you'd like the 'Colombia + Venezuela' continent (3 borders for bonus of 4) to be feasible)
La Vega // Melchor de Navarrete (Increases movement from southern part of the map to the middle and top)
Robert Jenkins // La Vega (If you moved the British boat closer to the island, otherwise it might just look weird )
Feel free not to implement any of these, they are just a few things I looked at while examining the map.
Good luck! You've got a nice start!
--Andy