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Is quī viā Latīnā venit per portam Capēnam Rōmam intrat.

Since it's all Accusative, I'm having a hard time figuring out what it means.

I'm guessing it might mean something like

He who comes from the Latin path/road enters through the ** door ... Capena ... Rome? **

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Remember that intrō takes an accusative, and per also takes an accusative.

Since there are multiple accusatives next to each other, by default, I'd assign each one to the nearest "accusative-taker":

Is quī viā Latīnā venit [per portam Capēnam] [Rōmam intrat].
He who comes from the Via Latina [enters Rome] [through the Porta Capena].

And indeed, this default interpretation seems to make sense, since the porta Capēna is the name of an actual gate in the walls of Rome.

Another clue comes from the fact that prepositions tend to come before their nouns—hence the name—and verbs tend to come after. It's not a hard-and-fast law, especially in poetry, but it's a good rule of thumb to keep in mind.

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  • Also, the Via Latina was the name of an important Roman road leading (approximately) east for 200km from Rome. However the Porta Capena area of Rome had become run-down and was demolished and rebuilt in the 2nd century, and the location was renamed the Porta Appia, which was the starting point of a different road, the Appian Way, connecting Rome to the coast at what is now Naples
    – alephzero
    Aug 26 at 15:12

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