Sailing in Sheboygan

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For the past 29 years, John and Loie Laimon have proudly contributed to the tight-knit fishing community that surrounds them by running their own fishing-and-bait business. Whether they are selling U.S.-made, handcrafted baits or other handpicked products, renting pontoons for small groups, or winterizing boat motors by fastening Santa hats to them, the Laimons approach each service personably and attentively. This approach has helped them grow to two locations on Pewaukee Lake.

129 Park Ave.
Pewaukee,
WI
US

Passengers on the Iroquois, Vista King, and Voyageur cruise ships have passed under century-old raising bridges and laid eyes on history-rich chunks of Milwaukee skyline. However, they've also sat under squadrons of F-18s performing barrel rolls over Lake Michigan. Licensed by the U.S. Coast Guard to perform tours and charters on the lake, Jake Chianelli and his captains offer their passengers a unique perspective on the city's waterside events. They also partner with the nonprofit organization Historic Milwaukee by using their trained docents to lead history tours, which include facts and anecdotes from the arrival of the first fur traders up to modern day.

With kitchen facilities and a full bar on board, each of the three double-decked ships are equipped for tours as well as a range of corporate events, wedding-rehearsal dinners, and Moby Dick-themed improv shows. Climate-controlled lower decks give passengers shelter in all weather, and open upper decks house a stage space where local indie-rock bands play during a summer concert series.

101 W Michigan St
Milwaukee,
WI
US

In 1977, a group of Milwaukee’s sailors responded to its city’s lack of a public sailing institution by banding together with county officials to create a not-for-profit organization accessible to everyone. The Milwaukee Community Sailing Center has continued to uphold this original vision of granting everyone—regardless of age, physical ability, or financial means—a chance to develop sailing skills while exploring Lake Michigan’s aqueous expanses. Since its founding, it has imparted its knowledge upon upwards of 100,000 student via hands-on classes and private lessons.

Throughout the summer’s balmy months, Milwaukee Community Sailing Center’s experienced and certified staff can be found reviewing boat safety with students during on-shore lessons or calling out instructions to their trainees from within a sailboat cruising around the lake. As winter’s frigid winds rage across the city, a host of off-season winter sessions enables skippers to keep their sea legs toned until spring returns. Bobbing cheerfully in the onsite marina, the center’s seaworthy fleet is comprised of more than 80 meticulously maintained vessels, including sturdy dinghies, cruisers, and saddled-up krakens. The center’s dedication to bringing the community together on the water is further evidenced in its outreach programs, including one designed to help Milwaukee’s at-risk youth turn a new leaf by helping them uncover hidden talents, develop leadership skills, and conquer their fears.

1450 N Lincoln Memorial Dr
Milwaukee,
WI
US

Though its staffed by a crew of student volunteers from the University of Wisconsin-Milwaukee, the Sailing Club at UWM has spent decades helping both the student body and community enjoy all aspects of sailing. Every year, from the end of April through late October, the group navigates Lake Michigan's waters aboard a fleet of sailboats that all either meet or surpass Coast Guard safety regulations. There are cruise boats designed for mild meandering, as well as sturdy Ynglings and Solings equipped with heavy fixed keels reinforced to maintain stability in turbulent weather or emotional break-ups. In addition to simple trips on the lake, members of the club can learn hands-on techniques from experienced sailors and participate in activities such as races, bonfires, and weekend cookouts.

1450 N Lincoln Memorial Dr
Milwaukee,
WI
US

Throughout the summer, the paved paths of Frame Park welcome outdoor enthusiasts of all ages and interests, including riders seated on High Roller Fun Rentals's unique bikes and pedal carts. Two-, three-, and four-wheel vehicles transport groups down the 1.7-mile river walk?a path flanked by playground equipment, picnic areas, gardens, and volleyball courts.

For those looking to make a splash, High Roller Fun Rentals also maintains a floating fleet of creature boats, canoes, and kayaks. These inventive vessels allow groups of two, three, or four to navigate the Fox River with ease. And for added convenience, the rental center hands out maps to encourage exploration.

1128 E Baxter St
Waukesha,
WI
US

Over the past year, CamRock Cafe & Sport—in partnership with the Village of Cambridge and Capitol Water Trails—has transformed the Koshkonong Creek from a tricky maze of fallen trees into a clear and gentle waterway. Situated on the shore of the creek amid miles of meandering snowshoeing, mountain-biking, and cross-country-skiing trails, the café ensures that its clientele doesn't need to look far for something to do. The staff helps visitors take advantage of the terrain with bike, boat, gear, and Go-Go-Gadget 'copter rentals. Hosted events bring people together to explore the trails via bike and listen to live music back at the café, or take part in a yoga or spin class. After guests return from a sojourn, the café supplies them with more than 100 craft beers, toasted gourmet sandwiches, and Alterra coffee from the food and drink menus.

217 West Main Street
Cambridge,
WI
US