"We would certainly like to cruise the Bahamas. However, we would really like to visit a Spanish speaking country since both our children are taking Spanish in school. Since they're also taking French, it would also be great to visit a French country but that doesn't seem possible."
You might also get some difference of opinion about "Spanish" being spoken in the Caribbean. Hispanic, Latino...many names but it won't be Castillian or Andalusian. As an Argentine-born friend of mine said on hearing "east coast spanish", "I know what espanish is, and that is not espanish." Of course, what your kids are learning in school may not be "real" Spanish either.
The USCG and US policies on Cuba would make it unwise to cross directly from the US into Cuba or vice versa, but I'm told that the US essentially ignores traffic coming/going via a third country, so that your course is not *directly* between the US and Cuba. Especially if there are no Cuban goods to be found on your boat when you do return to US waters.
The USCG sometimes is in a hard place between what the authorities require them to do, and the missions they would prefer to concentrate on, like SAR. So they've become fairly adept at walking a fine line and doing what they are required to do--and ignoring what they are allowed to ignore. (Like where you came or went to from Mexico, rather than the US.)