An accomplished racing sailor growing up in his native Germany, Philip had big plans for the family’s new sloop. Soon he was upgrading systems and, with the help of friends, making repairs in order to do a passage to Bermuda and back. Planning is second nature for Philip, who’s a software-implementation project leader by day. He drew up lists of tasks, tools, menus, and watch schedules. Over beers, potential crew gathered to go over details and look at charts, and they even practiced their suturing skills on sliced-open pigs feet, just in case. Then during the summer of 2008, Captain Philip and assorted friends sailed across the Stream, left the boat in Bermuda for a spell, then returned to bring the boat home. For several aboard, it was their first trip offshore, and, it turns out, it served as a training opportunity for the voyage to come because even then, the skipper was planning his next big escapade, a winter in the Caribbean. The model would be the same—captain and crew would share in preparations, sailing, and expenses—though this trip would be more complicated because of its four distinct legs and the time commitments required for each.