Moxie Marlinspike, in association with the Anarchist Yacht Club, is the filmmaker behind this "hastily made on a computer with a 14-day return policy" documentary about the everyman sailor.
After a short black-and-white photo-based history lesson about how the advent of fiberglass boats allowed for people outside top tax brackets to become sailors, and some of history's most maniacal sailing feats, the film focuses in on the four fixtures of the film; Lisa, a perfectionist overachiever with an unmatched attention to detail, a dedicated navigation aficionado named Allie, a strong-willed but often discombobulated crew member with a penchant for dropping things into the ocean going by Kirsten, and lastly the hippy narrator and sole male in the crew, Moxie.
The story begins with Moxie answering an ad in the newspaper for a $1000 sailboat located near Ft. Lauderdale, Florida. John, the man who placed the ad, picked Moxie up from a nearby train station and shuttled him to the canal that ran through his back yard where a Pearson 30 model sailboat resided. The condition of the vessel was a disparaging one - no mast, no engine, no fittings, no bulkheads, no hatch cover, just the fiberglass shell - but John offered to let him work on the boat at the ramshackle dock where it was located for a while.
After sending pictures to the others and getting the thumbs up, he pulled the trigger and bought it. He would spend three days working sunup to sundown on his own before the others joined him, after which they lived as vagabonds in a multi-million dollar Ft. Lauderdale home while working to get the boat sea-ready.
They would quickly learn that much of sailing is made up of working on the boat itself, where they found something was always breaking - there are few environments that are worse for wood and metal than being at sea. The remainder of the film is comprised of their travels through the Caribbean and then up the Eastern seaboard, with a multitude of pseudo sailing tips for the layman peppered in, and back down to Haiti where Moxie takes his leave from sailing and goes his own way.