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While exploring an Italian island, the Ross family's tour guide tells a story about Jessie's necklace, and how its curse brings anyone who wears it bad luck in love.
While on vacation, the Ross family finds a girl stranded in the middle of the ocean and invites her aboard their yacht. Meanwhile, Bertram stays home and babysits Mrs. Kipling, who has separation anxiety from Ravi.
In the final part of the "Rossed at Sea" three-parter, Jessie abruptly ends the Ross family vacation because the kids are constantly fighting. They wind up in a pickle when they find the yacht the next morning floating in the middle of the sea with no captain or crew in sight.