A New York City family's remarkable story of how they gave up their urban life, packed up their family of seven, and braved the difficult conditions of the Atlantic Ocean as they sailed 5,000 miles from New York to and around the Caribbean. Working the night shift as a temp in a high-rise cubicle, Erik Orton knew something had to change. He felt the responsibility of providing for his wife and their five children—the youngest with Down syndrome—but craved a life that offered more than just surviving. Watching the sailboats on the Hudson River during his sunset dinner breaks, Erik dared to dream. What would it be like to leave the hustle of the city and instead spend a year on a sailboat, somewhere beautiful, as a family? Despite having no sailing experience, his wife Emily's phobia of deep water, and already stretching every dollar to pay rent and buy groceries, the family of seven turned their excuses into reasons and their fears into motivation. Sure, they would miss their friends, the could go broke, they could get injured or die. Worst of all, they could humiliate themselves by trying something audacious and failing. But the little time they still had together as a family, before their oldest daughter left for college, was drifting away. The Ortons cast off the life they knew to begin an uncertain journey of 5,000 miles between New York City and the Caribbean, ultimately arriving at a new place within themselves. A portrait of a captivating and resilient family and a celebration of the courage it takes to head for something over the horizon, this is a deeply compelling story—told alternately by Erik and Emily—for all those who dream of leaving routine in their wake.