To celebrate their first anniversary, in 1997, Mandi Leonard and her husband, Scott, sailed a schooner from their Southern California home to Catalina Island. The couple—both avid seafarers—needed the break. Mandi was working 80-hour weeks as a traveling software sales rep, which she continued to do after having a child ("I'd breast-pump during meeting breaks, then FedEx the milk home," she says). That weekend they dreamed of a different future: "We thought, 'Wouldn't it be great to live on a boat?'"

Fourteen years later, the Leonards and their children—Griffin, 11, Jake, 9, and Luke, 5—relocated from a 3,200-square-foot home in Los Angeles to a 50-foot catamaran, embarking last July on a three-year sailing voyage that took almost a decade to plan. They started in the Caribbean and aim to end up near Indonesia, passing through the Panama Canal, South Pacific, and Indian Ocean. When the school year begins this fall, Mandi will take on teaching duties, guiding the boys through textbook-based lessons and tests that will be sent to an educational service to be graded.

Turning that fantasy in Catalina into a real-life fantastic voyage hasn't been easy—Mandi had to wait for the right time (after Luke learned to swim; before Griffin reached high school), and be certain she could keep the family safe. In addition to the family's several practice trips in the Bahamas, she studied hurricane schedules, compiled medical supplies (everything from antibiotics to a defibrillator), and learned to use a Taser should they encounter pirates.

By the end of the adventure, Griffin, Jake, and Luke will have completed eighth, sixth, and second grades, respectively. "We'll only be sails-up for about 10 percent of the trip," says Mandi; they'll spend the rest of their time in various ports, exploring local culture. The kids will alternate as "tour guides" on the different stops—first studying up on, say, the wildlife of the Galápagos Islands or the ancient ruins in Belize, then walking the family through the sights. "When you experience the world firsthand," Mandi says, "you really start to understand it."

Another thing they'll learn firsthand: the joy of realizing your biggest pipe dream. Says Mandi, "For years we wanted to stop fitting our lives to our work and live the life we wanted. Once we decided to do this, we never looked back."

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