Wisconsin, Lake Michigan Cruise from Milwaukee — 13 Days

Milwaukee WI, USA

Milwaukee sits on Lake Michigan, where a waterfront, lively markets and celebrated brewing heritage make a rewarding first impression. The Milwaukee Art Museum, with its striking wings designed by Santiago Calatrava, anchors the lakefront. Inland, the Historic Third Ward pairs restored warehouses with galleries, boutiques and restaurants. Follow the RiverWalk for public art and views of the city’s bridges. Then choose a brewery tour or a meal featuring Wisconsin cheese and local beer.

Sault Ste Marie, Canada

At the eastern tip of Michigan’s Upper Peninsula, Sault Ste. Marie offers a close-up view of a vital Great Lakes passage. Watch freighters enter the Soo Locks and rise or fall between Lake Superior and the lower lakes. Visit the Museum Ship Valley Camp for Great Lakes maritime history, or explore downtown’s shops and local landmarks. Along the St. Marys River, industry and northern scenery share the view.

Tobermory ON, Canada

Tobermory sits at the tip of Ontario’s Bruce Peninsula, where Lake Huron meets Georgian Bay. Here, clear water reveals historic shipwrecks in Fathom Five National Marine Park. Take a glass-bottom boat to Flowerpot Island, named for its distinctive rock pillars, or follow trails above the shoreline. In town, browse the harbour, then try locally caught fish as evening light settles over the bay.

Windsor ON, Canada

Windsor sits on the south bank of the Detroit River, directly across from Detroit, yet feels distinctly Canadian. Along the riverfront, landscaped paths and public art frame broad views of the American skyline. Downtown, explore Windsor’s French roots and its place in the Underground Railroad story. Make time for Windsor-style pizza, a local specialty with a loyal following.

Killarney ON, Canada

At the north end of Georgian Bay, Killarney is a small harbour with a remarkably wild hinterland. Killarney Provincial Park protects clear lakes and white quartzite ridges, the La Cloche range that inspired generations of artists. Paddle or hike beneath these pale peaks, or explore the shoreline by boat. Back in the village, watch fishing boats in the harbour and sample fresh whitefish. Quiet waters and expansive landscapes reward travellers who prefer discovery at their own pace.

Parry Sound ON, Canada

Parry Sound puts you on the doorstep of Georgian Bay’s rugged coastline, where pine-covered islands meet clear blue water. Boat tours thread the Thirty Thousand Islands, within a UNESCO-designated biosphere reserve. In town, the waterfront and Bobby Orr Hall of Fame offer a closer look at local life. Then linger over a meal beside the harbour.

Sault Ste Marie, Canada

At the eastern tip of Michigan’s Upper Peninsula, Sault Ste. Marie offers a close-up view of a vital Great Lakes passage. Watch freighters enter the Soo Locks and rise or fall between Lake Superior and the lower lakes. Visit the Museum Ship Valley Camp for Great Lakes maritime history, or explore downtown’s shops and local landmarks. Along the St. Marys River, industry and northern scenery share the view.

Great Lakes, USA

The five Great Lakes form an inland sea, holding about one-fifth of the world’s surface fresh water. From Chicago’s architectural skyline to Mackinac Island’s car-free lanes, each stop has a distinct character. Explore maritime museums, Indigenous history and working waterfronts shaped by trade and industry. Between ports, watch freighters cross open water as forests give way to dunes, lighthouses and limestone cliffs.

• Slate Islands ON (Scenic Stop)

Silver Islet ON, Canada

At Silver Islet, Lake Superior’s immense scale meets a mining story with an unlikely setting. In the 1870s, workers mined silver on a tiny island just offshore, home to one of Canada’s richest silver mines. The workings flooded and closed in 1884, but the settlement endures on the Sibley Peninsula, near Sleeping Giant Provincial Park. Come for the stark northern shoreline, then explore the traces of a remarkable boomtown.

• Terrace Bay ON (Scenic Area)

Sault Ste Marie, Canada

At the eastern tip of Michigan’s Upper Peninsula, Sault Ste. Marie offers a close-up view of a vital Great Lakes passage. Watch freighters enter the Soo Locks and rise or fall between Lake Superior and the lower lakes. Visit the Museum Ship Valley Camp for Great Lakes maritime history, or explore downtown’s shops and local landmarks. Along the St. Marys River, industry and northern scenery share the view.

Mackinac Island, USA

Mackinac Island makes an immediate impression: motor vehicles are prohibited, leaving streets to bicycles and horse-drawn carriages. Its harbor lies in the Straits of Mackinac, between Lakes Huron and Michigan. Walk up to Fort Mackinac for broad water views and a close look at the island’s strategic past. Then explore Victorian cottages, wooded trails and celebrated fudge shops along Main Street. Allow time to leave the waterfront and discover quieter lanes and the island’s natural side.

Milwaukee WI, USA

Milwaukee sits on Lake Michigan, where a waterfront, lively markets and celebrated brewing heritage make a rewarding first impression. The Milwaukee Art Museum, with its striking wings designed by Santiago Calatrava, anchors the lakefront. Inland, the Historic Third Ward pairs restored warehouses with galleries, boutiques and restaurants. Follow the RiverWalk for public art and views of the city’s bridges. Then choose a brewery tour or a meal featuring Wisconsin cheese and local beer.