Our boat scared us. In the late 1990s, when our family of four began our two-year cruise through the Caribbean, we had no experience with the Catana 40 catamaran we'd just bought in St. Martin. The 44- by 23-foot monstrosity felt huge and unwieldy. Our maiden voyage was a circumnavigation of the island with the boat's former captain, a Frenchman who was a bit nonchalant about big winds, waves, and other situations requiring caution. It was a brilliant blue day, and the four of us-my wife, Diane, our two daughters, and I-stood smiling and blinking into the sun. Le Capitaine was all smiles: "Bonjour! Comment allez vous? We go now, no?" I desperately wanted to learn everything he knew about the boat, so I paid close attention as we raised the monster mainsail at anchor. As we sailed clear of the north tip of the island, we were greeted by the winter trade winds and their roller-coaster waves. The Catana romped.