Tour guide in Milwaukee Don D.

I’m a lifelong Milwaukee native and certified sailing instructor with a passion for showing people the best of our city, from land and water. I’ve been sailing the Great Lakes for over 20 years and am certified by the American Sailing Association as both an instructor and a Master Mariner. Whether it’s exploring Milwaukee’s harbor by sailboat or walking through our historic neighborhoods, I love sharing the stories, culture, and beauty of this city I call home. When I’m not teaching sailing or leading flotillas in the Caribbean, I’m in Milwaukee helping visitors discover its charm. I specialize ins private, small-group sailing tours that offer an unforgettable view of the skyline, shoreline, and working harbor. I also offer on-land historical tours and harbor history experiences. My tours are hands-on, personalized, and always come with local insight. From Milwaukee’s industrial heritage and hidden beach towns to fish fries, sailboats, and shoreline sunsets—I’ll help you experience the real Milwaukee, not just the guidebook version. If you’re ready for a one-of-a-kind Milwaukee experience on land or at sea, let’s create your perfect tour together.