>>2634783>Has anyone here ever managed to /out/ in Cuba?Short answer is you can't. It's a communist dictatorship.
Longer answer is that nothing is geared towards randos wandering around and living as they please. There are no open markets. There are very few stores. The locals know when food is delivered and show up to buy the supply within hours. You can't hitchhike. Gringos weren't even allowed to drive city to city in private cars when I was there. You can't just wander out into the forest and build your camp. You can be shot for wandering into the wrong bit of the forest or onto the wrong beach. The cops are known randomly arrest tourists to shake them down for money.
People aren't 3rd world poor - I've lived in Bolivia, so I know what that looks like - but they don't have luxury either. Everyone has an education and a job, even though some of the jobs suck. No open markets. No homeless and no beggars. Well I did meet one woman begging. I turned her down and then noticed a guy who nodded to me. I assume he was a political cadre following her to make sure she wasn't bothering the tourists to much.
Long story short - if you want /out/ in the Caribbean, go to Puerto Rico or Dominican Republic. If you want /out/ in the jungle, go to Costa Rica, Equador or Chile. If you want the best rum and cigars in the world, on the roof of a hotel where Che and Castro used to hang out, go to Cuba.