I mentioned before about the History of Philosophy Without Any Gaps podcast as a great survey of the history of philosophy. One thing that stands out is that I do not think that either of the two popular stories we tell ourselves about the history of (especially Western) philosophy stand up all that well. There is the account that praises the classical Greek tradition, and then disparages tthe Middle Ages only to rejoice at the Renaissance and the Enlightenment. There is also the account that gives credit to the Middle Ages as a further enhancement of the classical tradition only to be wrecked by the Enlightenment.
The totality of Western philosophy seems much more continuous than that though. The themes that many associate with the Enlightenment are already in play in the medieval period, and these in turn were brought forward from the classical world (often via the Islamic world). There is no way that the Enlightenment could have sprung fully-formed out of the tail end of the classical period, and yet it also starts to appear to me to be so much the expected outcome of the medieval period too.