Meet the Captains

Welcome aboard! Endless Summer is led by a team of highly seasoned maritime professionals, each holding a USCG 50-ton Master’s license and years of experience navigating these waters. They hold National Safe Power Boating and U.S. Power Boating certifications and are able to teach private and group boating lessons. Their background in training and instruction always brings safety to the forefront of any day on the water. Beyond their technical expertise and unwavering commitment to your safety, our captains are passionate storytellers and local experts dedicated to providing a seamless, world-class experience on the water.

Captain Rob was born and raised at the head of the Chesapeake Bay near Perryville, Maryland. This area where the Susquehanna River flows into the bay is where it all begins. The bay offered year-round recreation, from fishing and relaxing in warm months to chasing waterfowl on the iconic Susquehanna flats during the winter. Captain Rob moved to the Annapolis area in his 20s, looking for new adventures and starting his beautiful family. With the South River as his new base, he began exploring the surrounding areas around the middle bay from Annapolis, Kent Island, West River, and local rivers. He spent evenings fishing and early mornings crabbing the South River, eventually getting his captain's license so he could share his passion for the bay and its beauty with anyone looking for an adventure. Rob has traveled the Chesapeake from top to bottom, with frequent trips to Washington DC, Norfolk, Chesapeake City, and everywhere in between. In 2025, Captain Rob decided to start Endless Summer Charters to share the beauty and mystique of the Chesapeake.

Captain Bill, older brother to Captain Rob, also grew up on the Susquehanna River. Captain Bill remains in Perryville, but is on the go moving boats up and down the east coast. Bill enjoys both sailing and power boats, and has taken several trips sailing the Caribbean with family and friends. Bill has spent countless days with a boat in tow running to every river on the eastern shore of Maryland looking for crabs and fish. Bill’s passion for the outdoors keeps him involved with several community groups teaching boys to fish, hunt and respect the outdoors.