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Sailing Into History: Remembering Our Old Boat

25 Years of Excellence on the Water

25 Years of Excellence on the Water

The Beginning

Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.

First Fleet Expansion

Due to increasing demand, Sea Dog Sailing added a second vessel, allowing more guests to experience private charters and guided sailing tours.

Award-Winning Service

Recognized for outstanding customer experience, Sea Dog Sailing received its first Best Sailing Charter Award, solidifying its status as a top-tier sailing company.

Specialized Experiences
Introduced

To cater to a growing audience, the company launched sunset cruises, proposal sails, and team-building events, expanding beyond traditional charters.

Luxury Upgrades &
VIP Packages

Sea Dog Sailing was founded with a passion for providing unforgettable sailing experiences. Starting with a single sailboat, the company quickly gained a reputation for its exceptional service and expertise.

Adapting to Change

Despite global challenges, Sea Dog Sailing implemented private charters with enhanced safety protocols, ensuring continued operation while prioritizing guest health and comfort.

Eco-Friendly Initiative

The company introduced sustainable sailing practices, including responsible waste disposal and promoting ocean conservation awareness among guests.

National Recognition &
Media Features

Sea Dog Sailing was featured in travel magazines and TV segments, highlighting its unique and memorable sailing adventures.

25 Years of Sailing
Adventures

Now celebrating 25 years in business, Sea Dog Sailing remains a trusted name, offering expertly guided sailing trips with the same passion and commitment that started it all.

Testimonials

Stories from the Sea

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

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Steffanie Gerkin profile picture
Steffanie Gerkin
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Had an amazing time on this stunning sailboat, will definitely be back to do this again!
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john hall profile picture
john hall
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We had a fantastic time sailing with Captain Matt in Lake Michigan from the shore of Milwaukee, WI. Recommended!
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Sean Ryan profile picture
Sean Ryan
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Had a fantastic sunset cruise with Captain Matt. He was ready to go and we started on time and went a little bit long. Matt made sure we were safe, made the best of light wind and was engaging the entire time. I highly recommend!
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J Andrew Geary profile picture
J Andrew Geary
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Excellent! I booked a sunset sailing trip with my family for our Milwaukee vacation. The communication setting up the trip was clear and the captain was responsive. The directions on where to go and what to prepare for were clear and very useful. We had an amazing time on the sailing trip! It was a beautiful night and the crew was great. The captain and his crewmate treated us very well and were a lot of fun to chat with during the voyage. I would not hesitate to recommend or even book another trip with Sea Dog Sailing. Thank you for a wonderful experience!
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Rachel MacGregor profile picture
Rachel MacGregor
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This was the BEST experience, I could not recommend it enough! I came to visit my sister in Milwaukee after she moved here and decided to try this because it sounded fun but it was by far our favorite thing from my entire visit (and I work in the travel industry so I am great at finding lots of fun things to do). Captain Bob was fantastic, so knowledgable about sailing and the lake and city, plus we got to try steering some which was really cool!
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Joseph Fasi profile picture
Joseph Fasi
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Magical and fun. Captain Bob was the best host and made the day spectacular. I have lived in Milwaukee for many years and have never savored the view of the skyline as we did from 5 miles out in Lake Michigan on a beautiful sunny day. He answered my incessant questions with patience and knowledge. I look forward to another charter with Sea Dog Sailing. the one down side— Now I have what may be a burning desire for a sail boat of my own!
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Noah Hunter profile picture
Noah Hunter
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Capt. Robert and his crew were so welcoming as soon as you walk down to the boat. If you have never been sailing you absolutely have to book a trip with this crew. My wife and I have never been and they made an amazing trip for both of us, explaining what they were doing with lines and sails, telling us how things work with the lake and sailing, and overall making us feel as comfortable and safe as possible. The boat is a beautiful vessel, the only downside was we wished we could’ve stayed and sailed longer! So if you’re in Milwaukee and want to experience something fun and exciting with a expert captain and friendly crew, book a trip with sea dog sailing!
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Scott Hartman profile picture
Scott Hartman
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Had a great time sailing with Captain Bob and his crew. 5 stars, would recommend!
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