Miss Penny is owned by one of DirtyBoat’s most loyal, long-standing customers and is expertly operated by Captain Chad Pruitt. With over 35 years of experience as a captain, Captain Pruitt has been an indispensable part of the DirtyBoat team for nearly a decade. He serves as our relief captain for the DB 2.0 and steps in as first mate whenever needed. With Captain Pruitt at the helm, you’re in capable hands and guaranteed to have an unforgettable experience.
Captain Mike, born and raised in the Florida Keys, has been exploring these waters since he was a child, giving him an unmatched familiarity with the area. Fluent in both English and Spanish, he brings a welcoming and inclusive vibe to every trip. Captain Mike’s passion for his work shines through in everything he does. When he’s not booked, you can often find him managing the pitt on DB 2.0 or Miss Penny. Known for his patience and enthusiasm, he’s fantastic with kids of all ages, making him a favorite among families!
Just Cuz is owned and operated by a true local of Islamorada, Captain Conan Yates. Born and raised in the Florida Keys, Captain Yates has an intimate knowledge of the waters and a passion for ensuring you have an incredible time. He’s joined by First Mate Captain Mike McDowell, who expertly manages the pitt. Captain Mike brings a wealth of experience, having run DirtyBoat’s pitt for nearly a decade before joining the Just Cuz team. With this exceptional crew aboard a stunning yacht, you’re in great hands and guaranteed to create unforgettable memories.