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The Peter and Paul Fortress
Designed to protect newly acquired lands from invading Swedes (it worked - the Swedes were kept at bay for almost three centuries and only now are able to realize their historic imperial ambitions through trendy restaurants, luxury hotels, and catering companies), the hexagonal shaped Peter and Paul Fortress lost its military significance before it was completed.
Its guns never saw any action and were put to use as a flood warning signal, and the fortress housed a political prison for two hundred years.
One of its first prisoners was Alexis, Peter the Great's own son, accused of subversion and treason and subsequently tortured to death under Peter's supervision.
Other famous prisoners interned here were the Decembrists (five hanged, over one hundred packed off to Siberia), Dostoevsky (subjected to a mock execution and exiled to Siberia), Lenin's brother (hanged), and the writer of revolutionary leaflets, Maxim Gorky (vilified as a hero of the socialist cause).