Our Story
Sea Dog Sailing was born from the love of the water, the wind in the sails, and the rich history of Milwaukee’s shores.
Founded by Captain Bob, a teacher whose passion for sailing and people was as vast as the waters of Lake Michigan, Sea Dog has set a course for adventure since its inception. Bob’s boundless enthusiasm for both the city and the sea created a legacy that still sails strong today.
Founded by Captain Bob, a teacher whose passion for sailing and people was as vast as the waters of Lake Michigan, Sea Dog has set a course for adventure since its inception. Bob’s boundless enthusiasm for both the city and the sea created a legacy that still sails strong today.
Matthew Scott, the proud new owner and helmsman of Sea Dog. Together with my dedicated crew of sailors, we are always prepared to set sail and navigate the vast waters ahead. I grew up along the shores of Grand Traverse Bay, Lake Michigan, where my great-grandparents built a small cabin that became the heart of countless summers spent with my family. It was there, on these waters, that my father passed down the art of sailing—a craft he himself learned from his father, who made the courageous voyage to Normandy during World War II. In my younger years, I worked on fishing boats, honing my skills and learning the intricacies of the Great Lakes’ diverse waters. Over the years, I’ve had the honor of commanding three large sailboats here in Milwaukee, each journey enriching my understanding of the maritime world.
Captain Matthew Scott, proud helmsman and owner of Sea Dog, leads a seasoned crew, always ready to navigate new waters. Raised on the shores of Grand Traverse Bay, Lake Michigan, he learned the art of sailing from his father—a tradition passed down from his grandfather, a WWII veteran who sailed to Normandy. Early years spent on charter fishing boats and small sailboats sharpened his skills, and commanding three sailboats in Milwaukee deepened his maritime expertise.
Captain Matthew Scott, the proud new owner and helmsman of Sea Dog. Together with my dedicated crew of sailors, we are always prepared to set sail and navigate the vast waters ahead. I grew up along the shores of Grand Traverse Bay, Lake Michigan, where my great-grandparents built a small cabin that became the heart of countless summers spent with my family. It was there, on these waters, that my father passed down the art of sailing—a craft he himself learned from his father, who made the courageous voyage to Normandy during World War II. In my younger years, I worked on fishing boats, honing my skills and learning the intricacies of the Great Lakes’ diverse waters. Over the years, I’ve had the honor of commanding three large sailboats here in Milwaukee, each journey enriching my understanding of the maritime world. Book charter page
Captain Matthew Scott, proud helmsman and owner of Sea Dog, leads a seasoned crew, always ready to navigate new waters. Raised on the shores of Grand Traverse Bay, Lake Michigan, he learned the art of sailing from his father—a tradition passed down from his grandfather, a WWII veteran who sailed to Normandy. Early years spent on charter fishing boats and small sailboats sharpened his skills, and commanding three sailboats in Milwaukee deepened his maritime expertise. He holds a 50 ton USCG Masters license with a sailing endorsement and has owned 3 sailboats in Milwaukee.
