Choose a currency
Private tour in Milwaukee Don D
Milwaukee Sunset Sailing Tour
-
2 hours
1
Tour date
-
2 hours
1
Don D.
5.0
Guide rating
1
Reviews
Tours delivered
74 hrs
Avg. response time
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.
Sail Into the Sunset: Relaxing 2-Hour Cruise with Stunning Skyline Views and Lake Breezes
Overview of your Milwaukee tour
Set sail into the golden hour with our Milwaukee Sunset Sailing Tour, a private charter for up to 5 guests. Departing from the scenic South Shore Yacht Club, this relaxing 2-hour cruise offers breathtaking views of the Milwaukee skyline, Lake Michigan’s sparkling waters, and the sun dipping below the horizon. Whether you're celebrating a special occasion or just looking for a peaceful evening on the water, this tour offers the perfect mix of serenity and adventure. Complimentary water and light snacks are provided. Guests are welcome to bring their own beer or wine to enjoy onboard. Sit back, unwind, and take in the beauty of a Milwaukee sunset—your unforgettable lakefront escape awaits.
Your Milwaukee tour itinerary
Arrival (15 mins before): Meet at South Shore Yacht Club for boarding and a quick safety briefing. Stow your items and drinks. Hour 1: Depart the marina and cruise past Bay View Park, the Lake Express Ferry, and into Milwaukee’s scenic inner harbor. Enjoy skyline views and landmarks like the Hoan Bridge. Hour 2: Sail out toward the breakwater for wide Lake Michigan views. Turn back for a golden-hour sunset over downtown. Light snacks and bottled water included; BYOB welcome (cooler provided). Return: Dock at SSYC as city lights glow. Optional photo op on deck or pier. Includes: Private captain, sailboat, water/snacks, Bluetooth speaker, and cooler with cups. Bring: Jacket, hat, sunglasses, favorite drinks, and your camera!
Want to customize this tour?
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 me know!
- You can request a specific meeting location (for example, your hotel) during the checkout.
Other details
Tour categories
Tour reference number
Languages
EnglishActivity level
FAQs
Who is this private tour in Milwaukee best suited for?
Where does the tour start and end?
Is transportation included?
How much walking is involved, and is it suitable for kids, seniors, or travellers with mobility concerns?
What languages is this tour offered in?
What's included in this private tour, and what should I budget for separately?
AI-generated. Please confirm details with your guide
-
2 hours
1
Tour date
-
2 hours
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.