Great idea ! Like you I have long regretted the gaps in my reading . A few years ago I decided to go right back to the beginning with the Greeks and Romans and carry on from there. At first I was really strict with myself and read strictly one period at a time but after realising that It would probably take me a decade to reach Shakespeare (and that I was getting serious Greek Tragedy indigestion) I decided to hop about time a bit .
I am looking forward to following you on your project :-)