Before you start the game, you can choose where to start.
The options are:
At sea,
Join a random krew,
Guinea,
Spain,
Brazil,
Labrador,
Or a random island.
You can not choose to start at Jamaica, but if you choose random, can you spawn there?
No, you can not
I don't think you could before but since the update that added new islands you can spawn at Jamaica if you choose to spawn at a random island.
What do you think?