The olive grove was planted in the 1880s or 1890s and according to Gherini "...demonstrates Caire's intent to make maximum use of the island's resources."

"In 1885, the Santa Barbara Daily Independent reported that the olive industry was attracting attention and that California was the only state that had a suitable climate for olives. The newspaper article pointed out that olives did well in dry, rocky soil unusable for other crops or grazing animals. This helps explain why Caire planted olive trees on the island. The island company probably harvested and produced the fruit for both island consumption and occasional sales. The olive grove, which has been unattended for years, still remains at Smugglers."

The eucalyptus trees around Smugglers Ranch were planted in 1887 under the direction of Justinian Caire. In addition, he had his laborers plant fig, walnut, plum, chestnut, orange, and acacia trees.