Americans are welcome in Cuba like any other tourist.
But no matter where you leave from, it's illegal for an American citizen or resident to travel to Cuba unless you comply with one of the 12 exceptions of the OFCA.
It is quite possible and while it is still technically a violation, no one cares.
Not trying to be a smarta$$ , but why would you want to spend one day in Cuba , when your already in the sunny south ?
What could you hope to accomplish in 24 hrs, other than to scratch it off your "bucket list" ??
A 24-hour stop in (I assume) Havana, while not giving you the time to see or do a whole lot, should at least give you an idea if you want to commit to an extended trip.
I don't think that's a fair comparison, if on a cruise, it's a given that your only gonna get a day in port, no visa, airport issues.
If your taking a day /overnight excursion into the city, still no big probs.
Flying from another southern destination for an overniter in Cuba is a little diff. don't you think ?
I personally don't see the logic in it, a week, four days, yes, a possible, but not an overnite.
It definitely wouldn't be something I'd want to do either, but I try not to judge. And besides, it's anywhere from 2 to 4 times as long as a cruise stop (i.e. those are usually 6 to 12 hours unless you're on a super-luxury cruise), so if you look at it as a similar kind of stop those extra hours might somewhat justify the hassle and expense.
Anyway, if OP is going to be in Turks & Caicos it seems to be moot, a case of "can't get there from here."
Well, they did say"like T&C" but either way, still seems like a lot of aggravation for a night ?