Island Living Tours Founder Leslie Diver Dishes Palm Beach Secrets

Leslie Diver’s wedged sandals she bought at a boutique inside The Breakers slip off her feet on the passenger side of an air-conditioned van in the middle of summer. They fall because she is turned around in her seat and propped up by her knees to face a group of six people during her 90-minute “Best of Palm Beach Tour.” The tour is put on by Island Living Tours, of which Diver is the founder. The lean, brunette 63-year-old’s hands, decorated in silver bands, become animated as she prefaces the attraction we’re about to pass on South Ocean Boulevard.

She calls it the “ham-and-cheese house” because of its sandwich aesthetic created through layers of red brick and coral keystone. Though, more interesting than the home’s design is who was its owner during the 1980s. James V. Sullivan was living in the house when he hired a hit man to deliver pink roses to his wife and murder her just hours before the couple’s divorce hearing.

Stories like these are a dime a dozen in Palm Beach island, which ranks as the country’s third wealthiest zip code. And Diver puts them all on the table like she’s dumping out her childhood piggy bank.

“The Breakers calls it the gossip tour, which isn’t exactly fair because it’s all factual,” Diver says with a laugh. But the sleuth-like nature of her information delivered with a touch of humor doesn’t stop the resort—and many others—from sending their guests on Diver’s tours. That’s because she is the best source on the island for history lessons, scandalous tales, picturesque views and insider knowledge.

Tours begin outside of Henry Flagler’s stately home (now the Henry Morrison Flagler Museum), which he built for his third wife, Mary Lily Kenan. Diver doesn’t live too far away—in an apartment on a quiet street near Publix with her Haitian-born adopted son, Gaby, and her mini dachshunds, Bobo and Bullet. When she first moved to the island in 1986 for a job as a stockbroker, Diver says she “bought the cheapest house in town on the crappiest street in town.” As she fixed up the Key West-style, 1,200-square-foot residence, she had to go in front of the architectural commission twice for approvals.

“One of the townspeople suggested I apply to be on the architectural commission,” she recalls. She did, and she served for eight years as the first and only female on the board.

As Diver was familiarizing herself with the town and its exquisite homes, she called the hotels on the island to ask if they could suggest a tour. Their popular response was: We have a good cab driver who really knows his way around. “I realized there was no tour business here, and so I started a tour business 14 years ago,” Diver recalls from the inception of Island Living Tours.

Now, Diver gives five to seven tours per week during season; some by van, some by bike and some by motor coach. With what’s left of her time she also works as a personal assistant and the special events coordinator for the Palm Beach Zoo and Hanley Foundation.

“[Island Living Tours] is definitely my happy business,” she says. “I tour normal people, I tour famous people, and everybody is wowed. I’ve never had anybody who is under-wowed by Palm Beach.”

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