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Perhaps the city of Umbar, some time during the latter parts of Gondorian rule?

I bet that would be an exiting city, a melting pot of different cultures and peoples; a place where goods and services from all around Middle Earth would be readily available for a price; a place where there's a little something for everybody, be they into history, art, partying, war or adventuring; a place where there's nice sunny weather, beaches, good food and drink, good women, and a bit edgy too, certainly not a quiet and safe old folks retreat.