Grandpa Dachshund tells his seven grand puppies about the adventures of Tiller, the dachshund who loves to sail, and Turnbuckle, the calico cat who saves his life. Tiller sails his boat, Dogspeed, down the Chesapeake Bay to St. Simons Island, Georgia. That's when the accident happens, and Turnbuckle must swim to Tiller's rescue. She and Tiller become friends, but trouble follows when Dogspeed disappears. The two set out on a quest to find the missing boat, but Tiller gets lost and encounters a man-eating alligator and two wacky seagulls. Things go from bad to worse when Tiller is captured by a gang of parrot pirates. He must find a way to escape if he is ever going to find Dogspeed, but Tiller is in for a big surprise