Private tour in Milwaukee Don D
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Don D.
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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.
Have a question or want to customize this tour? Message Don D.
Escape the city and experience Wisconsin’s small-town charm on this private shore excursion from Milwaukee. I’ll meet you at your cruise ship and we’ll travel north through the Wisconsin countryside to historic Cedarburg, a beautifully preserved 19th-century mill town along Cedar Creek. Explore limestone buildings, historic mills and charming Washington Avenue, with time to stroll the shops and Cedar Creek Settlement. From Cedarburg, we’ll continue through the countryside to Port Washington, a picturesque Lake Michigan harbor town with a working marina, historic downtown and beautiful waterfront. Along the way, I’ll share stories of Wisconsin’s immigrants, farming communities, Lake Michigan, local industry and the people who shaped the region. Private, relaxed and customized to your interests.
Milwaukee Cruise Port Pickup Meet at your ship and begin our scenic drive north. Wisconsin Countryside Travel through Milwaukee’s North Shore and Ozaukee County while hearing stories of Wisconsin history, German immigration, farming and Lake Michigan. Historic Cedarburg Explore Washington Avenue, limestone buildings, Cedar Creek, the historic mill district and Cedar Creek Settlement. Enjoy time for photos, shopping or a local treat. Covered Bridge Stop at Cedarburg’s historic covered bridge for photos. Port Washington Visit this picturesque Lake Michigan harbor town, including the marina, lighthouse, historic downtown and waterfront. Return to Milwaukee Enjoy the drive back with ample time built in for your ship’s departure. Approx. 5 hours total, including Cedarburg, Port Washington and return-to-ship buffer time.
Tell your guide which places matter to you, skip what doesn't, and tailor the experience for your group's needs. Not finding what you want? Message your guide to build something unique.
Travel in comfort in my beautiful Tuxedo Black Ford F-150, a spacious, clean and comfortable vehicle that’s ideal for exploring southeastern Wisconsin. The elevated seating provides excellent views of the countryside and Lake Michigan, while the roomy interior offers plenty of space for a relaxed private tour. Your tour includes door-to-door transportation from the Milwaukee cruise port, with plenty of room for personal items and anything you might pick up along the way.
2320 South Lincoln Memorial Drive, Milwaukee, WI, USA
I will meet you at your cruise ship's designated passenger pickup area in Milwaukee holding a sign with your name. Exact pickup details will be confirmed before your tour based on your ship's docking location. This is a private shore excursion, and our schedule will be planned around your ship's arrival and departure times.
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If your tour is valued over $200 USD and booked at least 45 days before the tour date, you can book with a deposit!
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