I just finished Surface Detail by Iain M. Banks....I'm hooked and have a couple of questions on the Culture novels:
- Is there an order to the novels (preferred or otherwise) ?
- What is the timeline of the novels ?
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I think the internal chronology roughly matches the publication order. But there's not much canonical information about this, most books don't contain a date. The Iain Banks Culture FAQ has a (tentative, not up-to-date) timeline.
The novels are self-contained. You can read them in any order. You might want to read the first novel first (Consider Phlebas) as an introduction to the Culture, but it's not strictly necessary.
As Gilles has said, the order is not really important.
Personally, I would read "Consider Phlebas" before "Look to Windward".
In some respects Look to Windward serves as a loose sequel to the first Culture novel, Consider Phlebas : the GSV Lasting Damage fought in the Idiran-Culture War, and Ziller specially composes a work to commemorate the arrival of light from a supernova triggered during the war.
I found that it gave me a better feel of the "Culture universe" having been exposed to the Idiran conflict, and the subsequent timescale that had elapsed, along with the huge scope of events.
According to this wikipedia page http://en.wikipedia.org/wiki/The_Culture#Novels if you put them in chronological order you get (Earth dates shown):
However, i'd recommend reading them in order of publishing, as that way you explore the universe in the same order as Banks did, and see themes develop etc.