It seems like the more I read, the more all roads lead to Dante, but many people are wary of paths through dark woods. A quick list of ways in.
In the beginner pile goes Charlie and the Chocolate Factory - Grandpa is Virgil and every child dives into their own circle when the hand of restraint is removed.
Read Stopping By Woods (Frost) for an exploration or English terza rima. He is playing with the style and has many thoughts himself on dark woods he can't explore yet.
The next three are my Inklings in Arms - Lewis, Tolkien, and Charles Williams with Descent Into Hell, Leaf by Niggle, and the Great Divorce. Each deserves its own post (or has one already)
Then comes the fun of plunging headlong into the comedy - Sayers translation recommended