In "Love in the Time of iPhones," Captain Rusty Cutlass and his crew continue their fish-out-of-water adventure in modern-day New York City. As they grapple with the challenges of 21st-century life, from confusing plumbing to perplexing fashion, Rusty finds himself drawn to Kara, a kind-hearted local who takes the "historical reenactors" under her wing. But maintaining their cover proves increasingly difficult as they navigate the bustling metropolis.

With Time Square's bright lights, subway "sea serpents," and a chaotic shopping spree, the pirates' antics reach new heights of hilarity. As Rusty and Kara grow closer, will he reveal the truth about his time-traveling predicament?

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