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.
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.
Stories from the Sea
Real adventures, real smiles — hear from those who made waves with us.
