Are there ever two ships on a private island?

At Castaway or Lookout?

No. There's only room for one. Sometimes while one is in port, another will pass by and blow their horn.
 

This was May, 2013. We were on CC and I took this picture. This is why I thought two could fit.

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And the same day, a third DCL ship also came by to wish the Magic on a safe journey to Europe. It was May 21, 2013!


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Not on a Disney private island. They each only hold one at a time.

Some of the other cruise line’s islands are a different story though and are designed to hold more than one ship per day.
 


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