Expeditions 1 - 3 Tips
For this discussion, the red treasure chests (TC) are numbered from the top. For example, in the Catalina Expedition (2nd expedition) the treasure chest in the top right of the island is #1, the treasure chest in the middle of the island is #2, and the treasure chest in the lower right of the island is #3.
There are 9 possible starts for each island. The navs can start in one of three possible locations. The pirates can also start in one of three possible locations.
Training Expedition (Expedition #1)
For this expedition only, the pirates use a simple attack strategy. Once you understand what the strategy is, you'll be able to at least get a Silver Cup.
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Catalina Expedition (Expedition #2)
Most of the time the main pirate attack will be around the #2 TC. Get most of your navs there quickly and then move the rest to the other nearby TC. That way, when the big fight around #2 TC starts you'll have a rested group.
Another approach is to get your runners quickly to #2 TC. There's a good chance you'll be able to do a fair amount of digging before the pirates get there, and if you get lucky you'll be off with the Treasure Chest before they can do anything.
Rosa Expedition (Expedition #3)
Since you only need 3 out of the 5 treasure chests to win, go for TC #2 and TC #3. As in the second expedition, move most of your team quickly into the area around these two. Send one nav (a digger) to the nearby TC to start digging. You'll probably have that TC all to yourself if the pirates don't start close by.