Wade and Hodges are downsizing to simplify their lives, but are going tiny in an unusual way -- on a sailboat! Their plan is to live and work on the boat while splitting time between Charleston, South Carolina, and the Caribbean. Wade's all about the sailing experience and wants a classic monohull, while Hodges is more concerned with the creature comforts of living aboard and prefers a catamaran. Can they compromise on a sailboat that fits both their needs?