A chance comment by someone else on the interweb over a decade ago is what first got me into classical history. Since then, I’ve read a reasonable amount on it, and thought a short list of suggestions for people thinking of dipping their toe into it might be handy.
The list is in no particular order, and I’ve linked to articles/reviews I’ve done if one catches your eye [some books have no review link because I read them before I started blogging].
Alexander, Hannibal, Caesar by TA Dodge
Theodore Ayrault Dodge was an American historian who wrote biographies/military histories around the three greatest generals of antiquity (entitled Alexander, Hannibal or Caesar).
There is a lot of detail, but it’s not written in a way that’s difficult to understand (indeed, Hannibal was the first classical history book I ever read). There are also a great many maps and illustrations, which is helpful for someone getting their first taste of classical history and who has no idea where Ephesus, Miletus and Halicarnassus might be.
The focus is strongly on the military. Lots of battles, strategy, explanations of cunning marches and the like abound.
NB Be careful you order the right book. Some abridged versions, not marked as such, have appeared. The full version should be around 700 pages for the first two, and almost 800 for Caesar.
John Julius Norwich’s Byzantium Trilogy
Don’t be scared off by the word ‘Byzantium’. I knew almost nothing, beyond that name, of Byzantine/Eastern Roman history before reading this trilogy. Afterwards, I was staggered I had such a gaping void of knowledge.
Norwich’s history is compelling, easy to read, and has a strong focus on the political and social dimension of the Eastern Roman Empire. Naturally, battles/military matters feature, but they only take centre stage when essential.
Apart from the very start (Constantine rather unhelpfully called his children Constans, Constantius and Constantine), there were rarely any moments I found difficult to follow, despite my dearth of knowledge. You’ll marvel at the idiocy of the Fourth Crusade, the brutal skill of Basil II, and the epic tragedy of Constantine Dragases’ death.
[NB technically, this is more Middle Ages, as it covers 4th to 15th century history].
Livy’s The War With Hannibal
A very accessible book, The War With Hannibal is Livy’s history of the Second Punic War (which had Hannibal as Rome’s antagonist-in-chief). It’s extremely easy to read, and the strong leading characters (Hannibal, Quintus Fabius Maximus, Marcellus, Scipio Africanus) give a personal narrative which makes things simple to follow.
Unlike Polybius’ version (which I enjoyed but is both missing the end of the war and a little drier), Livy covers the war from start to finish. In addition to military aspects, he covers the human side of things, of adversity and hope, triumph and disaster. He is biased towards Rome, but if you go in knowing that it’s a very good read.
Suetonius’ Twelve Caesars
Another very easy to read book, this covers Julius Caesar and the first 11 emperors in varying detail (Augustus was ruler for decades, Titus just a couple of years). Suetonius has a lively, engaging style, almost like a modern day tabloid or magazine writer. Although today’s historians dispute some of his assertions (particularly those involving Caligula) his tales are never dull. Suetonius does a very good job of conveying the impression the early imperial Romans had of their first rulers.
Legionary/Gladiator Manuals, by Philip Matyszak
The Unofficial Legionary/Gladiator Manuals are something a bit different. Although light in tone, with humorous asides (a mosaic was captioned something like “Having a leopard eat your face is one of the alternatives that makes being a gladiator seem like a good idea”) there’s actually a lot of accessible detail.
Unlike the other histories I’ve mentioned, these two books (there are three other non-classical books in the series) focus on the professions of being a legionary around the time of Trajan (early 2nd century AD, a high point for Rome) and a gladiator. There’s more day-to-day detail than the general histories above, and those who prefer a closer type of history rather than a focus on leaders may well prefer one or both of these.