1. C2C then Caribbean , you have this situation

No broken roads, no connection to Ft Lauderdale and Miami/KeyWest by Mantrid from C2C
2. Caribbean then C2C, you have this situation

Broken road left of Miami (no big deal - just avoid it), connection to Ft Lauderdale and Miami/KeyWest by Pilot from TerraMaps (much better than Mantrid's)
So it is player's choice. I myself choose option 2 because Key West is much better.