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“Did you ever think it would be this big?” says David Lester, a large man in a short-sleeved oxford, pointing at a 228-foot yacht that’s swarming with workers in a Miami shipyard. Lester, the founder of the Palm Beach International Fine Art and Antique Fair, is placing a $60 million bet that brokering high-end art on a high-end boat will become a lucrative new wave in the art market. “Up in Greenwich,” he says, perspiring in the 90-degree heat, “they don’t know what’s coming.”

Greenwich, Connecticut—headquarters to so many of the hedge fund managers who are pushing the art market to unprecedented heights—seems a fitting place to launch Lester’s SeaFair. On September 25, the vessel, christened the Grand Luxe, will host a fundraiser for Greenwich’s Bruce Museum before sailing to such upscale ports as Oyster Bay, New York; Hilton Head, South Carolina; and Palm Beach, Florida. Once aboard, invitation-only visitors will be able to browse the ship’s 28 galleries, dine in one of two restaurants, and relax at an open-air bar while contemplating how to spend their money.

The idea is to “take the gallery to the consumer rather than the consumer to the gallery,” says Lester, who with his wife, Lee Ann, started International Fine Art Expositions in 1990. Some of that firm’s events, like the Palm Beach show, were successful, while fairs in Houston and Hong Kong failed. The Lesters sold the company in 2001 for $18 million but stayed on as directors.

SeaFair, which Lester calls without irony “a Mark Twain riverboat for sexy people,” is an independent venture. The traveling expo arrives at a time when small and midsize art fairs are struggling to compete with big, thriving shows like Art Basel. To finance it, the Lesters put up an undisclosed amount of their own money and borrowed the rest. Lester says he has rented all 28 of the available gallery spaces for the ship’s maiden voyage. Many of these tenants are reputable second-tier dealers such as David Morris and Pelham Galleries, but there’s also one not-so-reputable outfit, Berry-Hill, which two years ago filed for bankruptcy protection after being sued in the wake of a bidding scandal at Christie’s. (The gallery later settled with the auction house.) Each dealer will pay $40,000 to $120,000 a month in rent, depending on shipboard location, which could eventually gross in excess of $20 million a year; Lester estimates his annual operating costs to be $12 million to $15 million.

“This is the smartest thing anyone is doing in art right now,” says Michael Goedhuis, owner of SeaFair exhibitor Goedhuis Contemporary, a New York-based gallery specializing in Asian art.

Not everyone is so buoyant. Top galleries like Matthew Marks and Gagosian, for example, will remain on terra firma. Sabrina Buell, a director at Matthew Marks, says her artists wouldn’t be able to produce enough work to sustain sales at a monthlong fair. There’s also the issue of protecting the art from the salt air. “There’s no rationale for putting a valuable work of art in that environment,” says Adam Lindemann, a New York collector and the author of Collecting Contemporary. “If you have to close it off and air-condition it, what’s the point of being on a boat?”

Lester is unfazed, saying the art-world elite is not his target audience. “The beginner is the best buyer; they’re easier sales than the Rubells,” he says, referring to Miami’s prominent collecting family. “For most people, art is an impulse buy.” The crowd at the top international fairs is the top 3 percent of collectors, he says. “I want the other 97 percent.”

Anyone who wants to visit SeaFair has to apply online and answer questions about his or her collection. But most of the art-related questions are merely a formality, Lester admits. “Their collection doesn’t really matter,” he says. “Preference goes to the person with the most money.” To get a sense of applicants’ buying power, Lester uses a range of market-research tools, including Zillow.com, a real estate site that lets users see satellite pictures of homes and get information on their value.

Will art lovers from places like Jacksonville, Florida, and Myrtle Beach, South Carolina, make SeaFair a success? Lester is about to get his answer. Meanwhile, he says his creditors have a contingency plan if the art barge sinks: Knock down the gallery walls and turn the Grand Luxe into a floating casino.