For those familiar with the writing and sailing accomplishments of Webb Chiles and his many voyages in small boats, a new short film about him is worth watching. The film follows the arch of Chiles’ sailing exploits on various craft, including his Moore 24 GANNET, which he completed his sixth circumnavigation on. Read more about Webb’s small boat sailing adventures in his article for Good Old Boat, “Little Wings” and watch the film below.

Webb Chiles was awarded the Cruising Club of America’s Blue Water Medal and the Ocean Cruising Club’s Jester Medal, and he’s published seven books and a multitude of magazine articles about his journeys. He bases his Moore 24, GANNET, at South Carolina’s Hilton Head Island. You can follow his online journal at

Editor’s Note: About the film, Webb Chiles says, “The film is nine minutes long. Naturally there are omissions in reducing 81 years, six circumnavigations, seven books, six marriages, another million or so words, and some other relationships, to nine minutes. However I like the film and do not believe that I could be portrayed better in that length of time. There are a few errors, as I did not have the opportunity to fact check it. Only one of the errors is of much significance and that is where in the opening title sequence it is written of me: ‘Six time solo circumnavigator.’  While I have circumnavigated six times, only three of those voyages were completely solo — the first, fifth, and sixth. I have always tried to avoid exaggeration or hyperbole believing that if you do it right, the plain truth is enough. The minor errors occur when a photo of THE HAWKE OF TUONELA is said to be RESURGAM, which is spelled incorrectly RESERGAM.  I hope you will view the film and if you find it worthwhile.”