In early December, Miami’s glittering skyline was disrupted by a gleaming 466-foot vessel pulling into its harbor. Sergey Brin, a Google cofounder, had decided to make a stop in style for the city’s Art Basel fair, arriving in a superyacht called Dragonfly.
Miami and its nearby coastal enclaves are fast becoming the staging ground for Silicon Valley’s grandest displays of wealth, and the showmanship is extending from seaside mansions to hulking yacht berths.
Over the past few years, billionaires like Brin and Amazon founder Jeff Bezos have shown off increasingly extravagant multi-deck megayachts, some as big as small cruise ships. The Dragonfly—with its movie theater, beauty salon, and multiple helicopter pads—is rumored to be worth some $450 million. Bezos has a 417-foot skiff called Koru that reportedly cost more than $500 million. And the Breakthrough—which one commentator referred to as a “modern engine...

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