Just to note, maps are not random. A map in a specific location always will take you to a specific other island.
Which maps show up is a little random however, and generally exclusive. For instance, on Bolo there is a map to Rusty Anchor. It is either guarded by the stack right next to where you spawn, or near the house of the Barbarian's Wife. The second one is really easy to get without fighting, but the first one you must fight to get (or do really hokey 'kiting').
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