Unlike Fred, Bob Auwood and Bonnie Handel didn't have to juggle jobs and sailing. They met in 1997 while cruising in the Bahamas. Bob was on his previous boat, Anaconda, and Bonnie was with some friends. Toward the second week of buddy-boating, Bonnie moved from her friend's boat to Bob's. Deciding it was time to turn her life around, she went back to Florida, quit her three demanding jobs, and flew back to the Bahamas to join Bob, who'd been sailing since 1990, when he took an early retirement from an investment bank on Wall Street.
For five years, they sailed Anaconda as far north as Canada, south to Trinidad, and west to Bonaire, until, back on the Chesapeake Bay, they saw the beautiful, round-bilged custom-built steel cutter Spray, and fell in love with her. In 2002, after they sold Anaconda, they set off aboard Spray, first to the Bahamas, where they adopted Abigail, a playful Bahamian pup, and then on to the Caribbean.