Aiken and his wife, author Zora, left Chicago for a one-year trip on a small sailboat, and the year became a way of lifeover twenty years of wandering by boat. During that time, both were able to devote time to writing and painting. They saw many of the water routes of the eastern third of the United States, and spent a number of winters in the Bahamas. He sold paintings through galleries and private showings at yacht clubs and resort hotels, while continuing to do editorial illustration and occasional commercial projects.

As they traveled, Zora wrote and David illustrated articles for magazines and newspapers, focusing on outdoor, travel, or lifestyle topics. Zora was a contributor to three magazines about boating. She also published a newsletter about small-boat travel. Together they wrote (and David illustrated) four books on outdoor subjects: two for recreational boaters, one for tent campers, and one describing the life of a Canadian outdoorsman.

David Aiken illustrated the Chadwick, the Crab books written by Priscilla Cummings. He also illustrated an ABC book by Ms. Cummings the sights, sounds, and feel of the Bay area for the youngest of readers. Most recently, David and Zora worked together on a children's book, Finding Birds in the Chesapeake Marsh: A Child's First Look. The book encourages children to spend time outdoors so they can see and appreciate all of nature.