Imagine The Canterbury Tales meets The Matrix ... that's The Hyperion Cantos (by Dan Simmons).
At some point in the far future, a group of seven pilgrims travel to the plant Hyperion to meet with a monster named "The Shrike." Over the course of their journey, they agree to share the stories behind their pilgrimages. That's The Canterbury Tales connection.
The stories build on each other and each develop particular philosophical and science fictional themes. The decline of humanity, the nature of consciousness, eternal life, forgiveness, love, duty, vengeance, artistic inspiration, and artificial intelligence ... Simmons covers a lot of ground in this narrative frame.
Without giving away spoilers, the books also take a fascinating spin on the future of technology. Reading them, I'm reminded of The Matrix, but Simmons' books have far more complexity and nuance.
The most fascinating story - to me - was the story about an ethical philosopher whose daughter caught a disease that causes her to age backward. His search for a cure leads him to the Shrike and to a tough choice: will he offer his daughter to the Shrike? This launches the narrative thread into an exploration of the Akedah and the biblical choice Abraham faced in Genesis when God called him to sacrifice his son Isaac.
The first two books in the series are definitely worth reading if you're into science fiction. Click here to check them out: The Hyperion Cantos.