The long tradition of barter trade between peasants, fishermen, and other inhabitants of Estonia and Finland established encounters over the Gulf of Finland. The petty trade was mutually beneficial as the parties could switch-trade their surplus means, exporting mainly salted herring from Finland and receiving grain products, mainly rye, from Estonia. The trade depended strongly on developing personal acquaintanceship with traders from the other side of the gulf. These formed a sort of partnership called sepra that could last for a season or even for years and decades. This chapter concentrates on the actual practices described during the trading encounters in this Finnish-Estonian arena, through writings, answers to questionnaires in archives, and literature.