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Private tour in Milwaukee Don D
Sails & Shoreline Private Sailing Tour
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2 hours
30 minutes
1
Tour date
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2 hours
30 minutes
1
Don D.
5.0
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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.
A Scenic Coastal Escape Along Milwaukee’s Hidden Shoreline Gems
Overview of your Milwaukee tour
Experience the charm of Milwaukee’s lakefront like never before on this private 2.5-hour sailing tour. Departing from South Shore Yacht Club, we’ll sail past the beautiful Bay View shoreline—one of the city’s best-kept secrets. Enjoy the serenity of open water, pause near a quiet beach for a floating picnic, and take in stunning skyline views. Light snacks and water are provided. Whether you're celebrating a special occasion or just craving time on the water, this relaxing sail offers the perfect blend of adventure and tranquillity.
Your Milwaukee tour itinerary
Board 15 minutes early for a safety briefing and intro to the sailboat. Then we’re off! Enjoy a scenic sail along Milwaukee’s Bay View coastline, passing parks, beaches, and skyline views. After about an hour, we’ll anchor near a peaceful beach for a floating picnic. Light snacks and water are provided—BYOB or bring a meal to enjoy onboard. We’ll sail back to South Shore just in time for golden hour. Included: Private sailboat with USCG captain, bottled water, light snacks, BYOB-friendly setup with cooler and cups, Bluetooth speaker, and blankets for comfort. What to Bring: Drinks, picnic basket, light jacket, sunglasses, and good vibes.
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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.
Transport details
Type: Private Transportation / Category: Boat
The Hunter 216 is a sleek, modern 21-foot daysailer known for its speed, stability, and comfortable layout. Designed with a large open cockpit and responsive tiller steering, it's perfect for relaxed coastal cruising or an exciting sailing experience. With room for up to 5 guests, this lightweight yet sturdy boat offers a fun and smooth ride ideal for harbor tours, sunset sails, and beginners alike.
What's included
What's not included
Meeting location
2300 East Nock Street, Milwaukee, Wisconsin, 53207, United States
Please meet in the parking lot of South Shore Yacht Club at 2300 E Nock St, Milwaukee, WI 53207. Once you arrive, contact your guide, who will escort you through the secure gate and down to the boat. Need a Ride? Private transportation to and from the marina is also available upon request—just let us know!
- You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
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AI-generated. Please confirm details with your guide
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2 hours
30 minutes
1
Tour date
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2 hours
30 minutes
1
Tour date
Book with a deposit
If your tour is valued over $200 USD and booked at least 45 days before the tour date, you can book with a deposit!
How it works
- Your credit card will be authorized only for the deposit amount.
- Funds will not be withdrawn until your tour booking is fully processed.
- 30 days before your tour date, the remaining balance is automatically charged.