La Habana, Cuba
Get there before it's invaded by American tourists! La Habana Vieja is an UNESCO World Heritage Site and it needs a lot of restoration work but I hope they don't ruin it in the process. Everyone seems pretty laid back and aside from the few hawkers wanting money for photographs you can safely wander around Old Havana day or night, just be aware of the holes in the street. Similarly there seemed no problems heading into any of the back streets of the other neighbourhoods.