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If you're not familiar with Greek myths, I'd start with those. Greek gods and characters are everywhere in the great books. Here's a good (and short) overview: https://www.amazon.com/Heroes-Gods-Monsters-Greek-Myths-eboo...).

Reading the books chronologically also helps. You'll understand more of the references and see how the books build on each other (https://en.wikipedia.org/wiki/Great_Conversation) e.g. Homer (Ilad) -> Virgil (Aeneid) -> Dante (Divine Comedy).

Modern translations are great too. You can always go back and read more "faithful" ones. Some good examples are: The Divine Comedy (https://www.amazon.com/Divine-Comedy-Dante-Alighieri/dp/0871...) and The Canterbury Tales (https://www.amazon.com/Canterbury-Tales-Retelling-Ackroyd-Cl...).

That said, the best approach may be: don't worry about it. Sure you'll miss things, but you'll get valuable insights too.

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