Let's try a radical, outside-the-box solution to our Cuba problem. The US should lift the embargo and negotiate a free trade agreement with Cuba. The immediate effect of such a deal would be a rush of American companies looking to offshore low-wage production to Cuba. The follow-on effect would be newly prosperous Cuban workers looking to spend money on material goodies. Access to modern goods helped ordinary Soviet citizens see what they were missing in a system of central planning. A little middle class spending in Cuba would go a long way toward breaking Communism's psychological grip on the island.
The US can declare victory in the last Cold War front in the Western Hemisphere. The Castro boys have one foot in the grave anyway. Opening up trade relations now would undermine any plans they may have for a familial transfer of power in the style of North Korea's Kim dynasty. The Cuban-American lobby may not like this approach but they are much less influential now than in the 1960s. If Richard Nixon could go to China, then modern American leaders can go to Cuba. Economic influence is an element of national power. We should use it to invite Cuba into the capitalist world.
Nota bene: I have never smoked a Havana cigar.