I actually started on this path after reading "The Ornament of the World - How Muslims, Jews and Christians created a culture of tolerance in Medieval Spain" by Maria Rosa Menocal, and then "Our place in al Andalus - Kabbalah, philosophy, literature in Arab Jewish Letters" by Gil Anidjar.
I wanted to know what had happened to the Jewish population once they left Spain, so I next read "Salonica - City of Ghosts - Christians, Muslims and Jews 1430-1950" by Mark Mazower, chronicling the history of Salonica from the arrival of the Spanish Jews to the Nazis sending over 50,000 Jews from Salonica by rail to their deaths in Auschwitz. From there I read a sweet little book, in Ladino and English, called "In Search of a Lost Ladino" by Marcel Cohen, and translated by Raphael Rubinstein. (Ladino being the language ofJudeo-Spanish - the language of the Jews of the Ottoman Empire)
Then, to read about another city, I read Orhan Pamuk's memoir of his native city - "Istanbul".
Both "Salonica" and "Istanbul" sent me next to the poetry of Nazim Hikmet, a poet banished from his homeland. I then read Orhan Pamuk's novel "Snow", with the central character being a poet who is returning to his homeland after a long period of banishment. To find out what the contemporary Turkish poets were writing I read Eda: An anthology of Contemporary Turkish Poetry.
at some point in all of this we rewatched the Costa Gavras movie Z, which is based on events taking place in Salonica (or Thessaloniki as it became)
A little lighter was The Janissary Tree, a mystery novel taking place in Istanbul in 1836, whose inspector, Yashim Togalu, is a eunuch of the court. The author, Jason Goodwin, also wrote thhistory "Lords of the Horizons: A History of the Ottoman Empire. and recently we have the new novel Birds Without Wings (set in the Ottoman Empire) by the author of Corelli's Mandolin.
We would welcome suggestions to add to this list, or comments on titles (or travel to Turkey). Thanks!