Whether you have an emotional connection to the place or seek a firsthand look at the complex politics surrounding Cuba, you should go. If you're thirsting for a Caribbean experience that isn't overrun with private beaches or de facto segregated tourism (where tourists and a country's residents don’t interact), you should go.
For me, a first generation (non-Cuban) American, Cuba is an idiosyncratic, vibrant, cultured, and incredibly beautiful place. There are things about Cuba, for better or worse, that I likely will never see again in my lifetime. For example, there are no advertisements anywhere in Cuba, and in their theoretical places are colorful socialist slogans and images of Che Guevara painted on billboards and the sides of buildings. There are interracial couples as far as the eye can see. The streets are filled with makers who have used every kind of upcycled material to create art, jewelry, and furniture. There are few homeless people. It’s one of the only places that I, a woman, can walk alone at night and not worry about my safety. And then, of course, there’s a big aesthetic pull for many: Americana nostalgia for classic cars from the '50s and a colonial backdrop. If you decide to travel to Cuba, proceed with the awareness that you are neither entering a wonderland, nor a museum.
