The Port of Sheboygan has a modern and scenic riverfront on the Sheboygan River and a beautiful lakefront on Lake Michigan that make it a popular tourist destination. Known as the "Spirit on the Lake," The Port of Sheboygan Riverfront district is home to fishing shanty shops, and the South Pier is a one-acre indoor entertainment center with a huge waterpark. The John Michael Kohler Arts Center contains the original home of the industrialist as well as a performing arts venue that offers music, dance, and theater performances; an arts-based preschool; tours; demonstrations; and classes. There are frequent festivals that enliven summers in the Port of Sheboygan.

The Port of Sheboygan has a humid continental climate with warm humid summers that can get hot and cold winters that can be severe. Temperatures in the Port of Sheboygan range from an average high of 22°C (72°F) in July and August to an average low of -6°C (20°F) in January. Precipitation ranges from an average of ten centimeters (four inches) in August to about 3.8 centimeters (1.5 inches) in February. Snow comes to the Port of Sheboygan from mid-October through mid-May, peaking in January at about 37 centimeters (14.5 inches). Humidity levels are lower in winter (78% in January) and rise to about 88% in August and September.

The heart of the Port of Sheboygan is her harbor at the mouth of the Sheboygan River as it enters Lake Michigan. The Port of Sheboygan Lakefront offers many opportunities for relaxation and activity. Just north of the harbor, Deland Park has beautiful beaches, a popular yacht club, and boat launches. People enjoy taking walks along the beach and one of the Port of Sheboygan breakwaters, with a lighthouse at the end, that extends for half a mile into Lake Michigan. In the fall and winter, when the wind is blowing right, surfers paddle into Lake Michigan from the beach. There are also several trails along the lakeshore that offer great opportunities for long walks and bike rides.

The Riverfront in the Port of Sheboygan is the starting point for the city's popular boardwalk that extends along the River through downtown and into Lake Michigan. The boardwalk features coffee houses, fine dining, unique shops, an ice cream parlor, charter fishing, and mini-golf. The Port of Sheboygan Visitor Center is located on the Riverfront at The Map & Globe Exchange.

Harbor Centre offers many opportunities for recreation in the Port of Sheboygan. The Blue Harbor Resort and Spa is a 1.2-acre family entertainment center with luxurious accommodations and the Breaker Bay Waterpark, a year-round indoor waterpark that maintains a comfortable °C (84°F). Visitors can explore restored fishing shanties that now house shops and restaurants. The Port of Sheboygan's South Pier offers mini-golf and an ice cream shop where people can watch the fishing boats return with their catch. Harbor Centre Downtown has a wide range of shops, restaurants, services, accommodations, and entertainment.

The new Military Heritage Museum in the Port of Sheboygan honors veterans and educates the public about military history. The grand opening of the museum in the early summer of 2013 introduced the collection of military memorabilia and education programs. Groups can schedule day trips and overnight dock-side cruises from the Port of Sheboygan to learn what it was like to serve on-board a naval vessel.

Located in the downtown Port of Sheboygan, the John Michael Kohler Arts Center is a museum and performing arts center. Listed on the National Register of Historic Places, the original Kohler house is located in the museum. Some 160 thousand people visit the facility each year. It contains ten galleries, a theater, meeting and performance spaces, and studio-classrooms. The ARTery is a family-oriented activity space that enchants children. The Center's adjunct site is called ARTspace for exhibits and shopping in the village of Kohler. In addition to performances, art exhibits, and festivals, the Center offers arts-based classes, lectures, and tours. Well known for its artist-created bathrooms, the Port of Sheboygan's John Michael Kohler Arts Center hosts artists for two to six months when they can create works using industrial equipment and materials.

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