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Bosra
A Roman theatre wrapped in a medieval fortress, built of black basalt. The south of Syria in one afternoon.
Bosra was the capital of the Roman province of Arabia. Its theatre seats fifteen thousand and survived because the Ayyubids turned it into a fortress, wrapping the stage in walls and towers. You walk through a castle gate and come out in the second century.
The old town around it is built from the same black basalt, still lived in, with a mosque said to be among the oldest in Islam and the ruins of a cathedral.
Bosra is a day trip from Damascus, two hours each way, or a stop on the way south. Combine it with a lunch in Suweida and the Druze villages of the Hauran.