Aus_Snow said:
The situation is that I don't own much in the way of history books
Dear goodness! Are you ok? Was there a fire?

OK, ok, that was probably only to my self-consciously bibliomaniac and history-obsessive mind. Sorry.
What would be particularly great is if posters could recommend a good writer (or selection of good writers) whose works cover several cultures, eras and/or geographical locations. Writing style is of prime importance too (well, after factuality and comprehensiveness.) The thing is, I'll persist in reading most things, but some writing styles put me off to the extent that I won't necessarily digest all the information. I know it's largely a subjective thing, but if people could give a reason or two why such-and-such's writing style is so good, that'd be doubly useful and appreciated.
I can second Manchester's
World Lit Only By Fire for readability. I'm aware of there being controversy over some of its content, but I'm not familiar enough with the dispute to know much beyond that it exists. I have the vague sense that it has a bit to do with an uncharitable reading of the Middle Ages, but I could be totally wrong on that. I read it in high school, back before I was regularly reading history.
For a macro perspective on the generalities of geography and development, there's always Jared Diamond's
Guns, Germs, and Steel. The logical companion volume is his
Collapse which I haven't finished. I know very little about biology and ecology, but he came across very clearly to me despite that.
For Antiquity, (Greece, Rome, that particular set of dead people) I can recommend Norman Cantor's
Antiquity as both readable and funny, in a whirlwind tour kind of way. I recall it being more topical than strictly narrative, which could be off-putting. He'll have a chapter on the Greek intellectual tradition, then a chapter on the Jewish, etc. His
The Last Knight gives a very good picture of what great nobles actually did in the late Medieval period.
In the Wake of the Plague is good too. My general experience with Cantor has been very good. If you can handle one book by him then you're probably ok with the rest of his mass-market opus. He does tilt fairly strongly towards political, intellectual, and economic history. Not the guy to go to for much on how the average peasant lived, perhaps.
If you're a bit more ambitious and not afraid of some philosophy (which the author explains lucidly enough) then a great book on the transition from the classical world to what we know as the Middle Ages, then Freeman's
Closing of the Western Mind may be the thing for you. It's big enough in scope, but friendly and not afraid to name names. Cantor's
Civilization in the Middle Ages (which is as big as it sounds) covers some of the same material from a more closely political angle.
Or at least these are the things I find readable. But hey, it's aesthetics. Spend some time at a B&N reading the first few pages and see how well you like the style.