When Allen Ware, 62, a California-based Google executive, decided it was time to satisfy his vacation wish list goal of chartering a “big yacht” in Italy, he soon learned that the process was far more complicated than searching online and booking a boat. Ware was no stranger to sailing: He had previously booked sailing boats and catamarans in the British Virgin Islands, some of which he’d captained himself. But with superyachts, he felt over his head. Evaluating ships based on photos, then differentiating between charter companies and individual brokers, he said, made the whole concept feel impenetrable before it even began.

Like anything else, researching online and scouring reviews is the first step. But then, Ware advises, you have to trust the broker with everything else. “That trust is important,” he explains. “It’s nerve-wracking when you have to wire over $50,000.”

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