Im with fluffy, fonts 1 or 5 (1 is better to me).
Yeah, the routes suck. Make them clearer. I would suggest complete lines, but smaller gaps could work too.
More little things:
Some continents have many borders... mainly central america and greater antilles. Maybe you should remove the connection betwenn Jamaica and Honduras.
Do we really need that country called Mississipi? The name is big, so it doesnt fit well. You could change the name, or merge with another country (this would bring the number of countries to 42 again). If you want maintain the main structure the same, maybe you could split texas.
I still think the names to the little islands are not ok. The names dont need be exact. You can change some names, using names of the capitals or something alike. For example, how about Dominica instead of R. Dominicana? Or Trinidad instead of Trinidad & Tobago? So you could probably make the names clear, without confusion. For same purpose, you could remove the "DT" of México "DT".
The Bahamas country is confusing. Please delete the smallest non-necessary islands.
The continent bonuses could have an adjustment. If you realy delete the route Jamaica Honduras, bonuses could be:
Small Islands - 2
Bigger Islands - 3
South America and USA - 4
Central America - 5
Mexico 6 (or 7)
Are you planning some final art? Maybe a skull and crossed bones