Challenge: Super-fortified Aegean Sea, every single island is a fortress

What if there was a clash between empires in the pre-modern era that caused the Aegean Islands to be the most fortified places in the world at the time? Is it possible?

What would be most interesting or plausible: a classical version as a stagnated Greco-Persian Wars, an early medieval version as an ongoing Arab-Byzantine Wars, or a Renaissance version with Venetians and Crusaders battling the Ottomans?
 
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What if there was a clash between empires in the pre-modern era that caused the Aegean Islands to be the most fortified places in the world at the time? Is it possible?

What would be most interesting or plausible: a classical version as a stagnated Greco-Persian Wars, an early medieval version as an ongoing Arab-Byzantine Wars, or a Renaissance version with Venetians and Crusaders battling the Ottomans?

The lattermost is IMO the most plausible since the uppermost limit of architecture is highest. Also, the broader empires mean that someone has the ability to organize food for all those forts.
 
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