WEATHER
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Three ships out of Palos, west into the empty Atlantic, following the Sargasso and whatever hope you brought. Land is somewhere out there. Probably. The crew's opinion on this calcifies weekly.
Sail the actual route around the world: strait at the end of America, the vast Pacific, a quarrel you should not join, and home by the Cape of Good Hope. Most of the crew will not make it. Most of the crew is aware of this.
Around the stormy cape, trade down the Swahili coast, buy pepper for almost nothing in Calicut, and sail home pretending the return leg was always the plan.
A randomly chosen venture, randomly chosen misfortunes, and market prices that make sense approximately when it is too late. Ideal for learning which barrels are worth it.