Angra dos Reis: 114km (71 miles) SW of Rio de Janeiro, 246km (153 miles) NE of São Paulo
One man's paradise is another man's prison, quite literally in the case of Ilha Grande. During Brazil's long years of military dictatorship, the prison on the far side of the island was where the generals sequestered political prisoners, throwing them in the with the general population in the expectation that these effete intellectuals would get eaten alive. As it turned out, the political prisoners had solidarity and revolutionary theory on their side. Not only did they manage to dominate the general population, but they soon began to recruit among the other prisoners for the cause, imparting to these new cadres all their hard-won knowledge of revolutionary theory and urban guerilla warfare. With the return of democracy, the middle-class revolutionaries returned to politics, while the criminal cadres put their new skills to use revolutionizing the theory and practice of crime. The citywide drug syndicates that now control the favelas in Rio de Janeiro and São Paulo can be tracked back to lessons learned in the presidio of Ilha Grande. (A 2004 film version of this story, Quase Dois Irmãos [Almost Brothers] featured a screenplay by City of God author Paulo Lins.) The remains of the prison can still be seen on the island's windward shore, but that's not what draws people to Ilha Grande.
Instead, the reason most people sentence themselves to a stint on the Big Island has more to do with pristine beaches, turquoise ocean water, and green rainforest hills running from shoreline up to peaks over a thousand meters high. For the active, there's schooner tours and scuba diving, kayaking, rainforest hikes to hidden waterfalls, surfing and bodyboarding, and sailing. For the sedentary, there's quiet and calm and some of the prettiest beaches in Southern Brazil.
The main town on Ilha Grande -- and the spot where the ferries and boats from the mainland arrive -- is Vila do Abraão (often just Abraão), a not very big collection of pousadas and restaurants on the island's eastern end. Numerous other pousadas are tucked away on small bays and beaches around the rest of the island. Spend a few days here and you may find you've lost all will to escape.