2 more Lake Michigan Wisconsin stops: Sheboygan and Milwaukee!

Thursday, August 20 through Monday, August 24, 2026

8/21/20263 min read

On Thursday, August 20, we left at 8:00 from Manitowoc on beautiful smooth waters. It was only about 25 miles to Sheboygan but we decided to go fast because we needed to watch a lifestream of daughter Carolyn's orientation to Law School called the Pinning Ceremony at 10:30. It was a great ride and my kind of pleasure boating which doesn't always happen on the Loop. We arrived at 9:30 and took on diesel fuel (280 gallons) and got plugged in just in time for the 10:30 ceremony at UK Law School. Harbor Center Marina has a nice facility and gave us great maps and tourist information for Sheboygan. Later in the afternoon we stopped by Sheboygan Yacht Club since we are reciprocol members and had an appetizer. It is a beautiful  club at the entrance to the harbor and the people were welcoming. We went to Sly's Midtown Saloon to have a brat since Sheboygan says it's the "bratwurst  capital of the world" and the food was quite good there. We had dessert and wine at Stefano Trattoria. It was the best tiramisu I had ever had! 

On day 2 in Sheboygan, Friday August 21, we rested and did chores since it was raining all morning. When the rain stopped we did some more exploring of Sheboygan by taking the $1 trolley ride around the city. The trolley stop was right by the Lottie Cooper shipwreck exhibit. From the trolley we saw the world's tallest flag pool (400 feet) at Acuity Insurance. We saw the John Michael Kohler Art Preserve building but did not go in this time. We may take a road trip there after we get home. We did some shopping at some local markets: Nature's Best and Stefano's Slo Food Market. We walked and saw the sights on Sheboygan's River Walk and had pizza at Harry's Prohibition Bistro located on the Sheboygan River.  Sheboygan has a lot to offer and we enjoyed our time there. 

On Saturday, August 22 we left early for Milwaukee since there was a window of favorable weather. It started out pretty calm and we saw many fishing boats and sail boats. When it was less calm we took it up on plane. On the way there I was looking at the map on my phone which I am in the habit of doing to see what towns we are near as the chart plotter has limited information. In doing so I noticed Concordia University on Lake Michigan. I knew our  great niece Taylor would be starting college soon at a Concordia University but didn't realize exactly where it was. I texted her mom, our niece Jennifer, and found out the whole family was there dropping her off for freshman year!!  Taylor said she would look for our boat as we went by so we got as close as we could and took a photo of her campus and she snapped a photo of our boat passing by. It's hard to see in the photos but she was at the bottom of the long stair case down to the water and the photo of us she took from the beach at the bottom. We didn't want to chance getting too close since there were shoals. Her parents and brothers were staying in Milwaukee.  After we got to Milwaukee they all  met us at the Milwaukee Yacht Club where we were docked. It was a serendipitous opportunity that we were there at the same time and hadn't realized it and a great time seeing the whole family: Jennifer, Ryan, Taylor, Alex and Carson. We had lunch there and visited on the boat. It rained a little but we were treated to a beautiful rainbow. After they left Tim and I enjoyed appetizers and desserts at the brand new patio at the Milwaukee Yacht Club. 

On Sunday, August 23, after worshiping with our church online, we took a walk over the pedestrian Brady Street Bridge and picked up some provisions from Walgreen's. In the afternoon we enjoyed some pool and hot tub time. We met a lot of nice people, including Dave and Karen who were very welcoming and we enjoyed discussing our military service with them. We had dinner inside the beautiful dining room at the Milwaukee Yacht Club.   Monday, August 24 was our last day in Milwaukee and we took a walk along Milwaukee Bay past several landmarks such as the beautiful Milwaukee Art Museum, Veteran's Park, and the paddleboats on the lagoon that are shaped like swans! We had breakfast at Colectivo  Coffee which is located in the old flushing station. We rested in the afternoon and also had the chance to look at a Regal 42 Sport Coupe, a type of boat  we would possibly like after the Loop. In the evening we took a walk on Lake Michigan to the north of McKinley Marina and had a brat and hot dog at the Roundhouse Beer Garden at the McKinley Marina. We are excited to head to Waukegan and Chicago, Illinois next!