Wisconsin, Lake Michigan Cruise from Milwaukee to Kangerlussuaq — 25 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.

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.

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.

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.

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.

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.

Welland Canal, Canada

Few waterways make engineering feel so immediate as the Welland Canal. Here, ships rise and descend through eight locks to bypass Niagara Falls, linking Lake Ontario with Lake Erie. Watch freighters pass at close range, then explore the canal’s shoreline communities and maritime history. Welland and nearby St. Catharines offer a distinctly Canadian perspective on this vital Great Lakes shipping route. The experience is measured not in grand monuments, but in scale, movement and the patient choreography of water.

Toronto, Canada

Toronto rewards a day ashore with a skyline made for lingering and neighbourhoods best explored on foot. The CN Tower rises above a city whose residents trace roots to more than 200 ethnic origins. Take the ferry to the Toronto Islands for open lake views. Back downtown, choose the Art Gallery of Ontario or the Royal Ontario Museum. Save time for St. Lawrence Market, where local produce and prepared food make an easy, memorable lunch.

St Lawrence Seaway, Canada

Canada’s St. Lawrence Seaway is a working passage between the Atlantic and the Great Lakes. Its canals and locks lift ocean-going vessels past rapids and dams, revealing the scale of a remarkable feat of engineering. Along the route, Quebec’s riverside towns, Montréal’s historic waterfront and Lake Ontario offer distinct shore excursions. From deck, watch freighters negotiate locks at close range; shore visits reveal French-Canadian culture and maritime history.

Montreal, Canada

Montréal is a city of French character and North American energy, best explored on foot. From the Old Port, cobbled streets lead to Old Montréal’s grand squares, cafés and Notre-Dame Basilica. Climb or drive up Mount Royal for a broad view of the skyline and the St. Lawrence River. Then follow the city’s appetite, from market produce and bagels to inventive French-Canadian cooking. Allow time for the museums and lively terraces; Montréal’s pleasures are close together, but never feel hurried.

Quebec City, Canada

Québec City is best explored on foot, where French-speaking Canada feels unmistakably distinct. Within the UNESCO-listed Historic District, stone walls, steep lanes and 17th-century façades tell the story of New France. Ride the funicular between Upper and Lower Town, then browse Petit-Champlain’s boutiques beside the St. Lawrence River. Allow time for the Plains of Abraham, where a pivotal 1759 battle changed the course of Canadian history. Come ashore ready to climb; the finest views reward a little effort.

Tadoussac, Canada

At Tadoussac, the St. Lawrence meets the Saguenay in a dramatic seam of cold, whale-rich water. From shore or a small boat, look for belugas and minke whales; humpbacks visit in season. Follow headland trails for sweeping river views. In the village, the Petite Chapelle dates to 1747 and is often described as Canada’s oldest wooden church. Tadoussac’s fur-trading post, established in 1600, anchors its long history.

St Lawrence Seaway, Canada

Canada’s St. Lawrence Seaway is a working passage between the Atlantic and the Great Lakes. Its canals and locks lift ocean-going vessels past rapids and dams, revealing the scale of a remarkable feat of engineering. Along the route, Quebec’s riverside towns, Montréal’s historic waterfront and Lake Ontario offer distinct shore excursions. From deck, watch freighters negotiate locks at close range; shore visits reveal French-Canadian culture and maritime history.

Woody Point NL, Canada

Woody Point sits beside Bonne Bay, within Newfoundland’s Gros Morne National Park. From its harbour, roads lead to the Tablelands, where exposed mantle rock sets the landscape apart. Visit the Gros Morne Discovery Centre, stroll the waterfront, and look across the bay to its steep-sided shores. Historic buildings and local cafés make a welcome pause between outdoor excursions.

Red Bay NL, Canada

Red Bay sits on Labrador’s rugged coast, where the Atlantic still sets the pace. In the 1500s, Basque whalers crossed the ocean to hunt right and bowhead whales here. Their remains form one of North America’s most important early industrial sites. Visit the UNESCO-listed archaeological remains and interpretation centre, then look across the harbour toward Saddle Island. Come for the whaling history, sea air and striking sense of distance.

L'Anse aux Meadows, Canada

At Newfoundland’s northern tip, L’Anse aux Meadows offers a rare encounter with the Viking age in North America. Archaeologists uncovered evidence of a Norse settlement here dating to about 1,000 years ago. UNESCO recognizes L’Anse aux Meadows as the only confirmed Norse site in North America. Walk among reconstructed turf-walled buildings, then explore the visitor centre’s artefacts and archaeological evidence. Beyond the site, the wind-shaped coastline rewards a slower look.

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Ilulissat, Greenland

Ilulissat stands beside Disko Bay, where icebergs drift from the Ilulissat Icefjord, a UNESCO World Heritage site. Sermeq Kujalleq, one of the world’s fastest-flowing glaciers, sends vast blocks of ice into the fjord. Walk the paths above the water, visit the local museum, or join a boat trip among the icebergs. From shore, their scale can be difficult to grasp. Ilulissat pairs a working Greenlandic town with one of the Arctic’s most striking landscapes.

Sisimiut, Greenland

Set just north of the Arctic Circle, Sisimiut is Greenland’s second-largest town and a working fishing port. Brightly painted homes rise above the harbor. Boats and fishing vessels keep the waterfront firmly connected to daily life. At Sisimiut Museum, historic buildings and collections reveal Inuit heritage and the town’s colonial past. From town, trails open onto Arctic landscapes of mountains, lakes and broad tundra.

Kangerlussuaq, Greenland

Kangerlussuaq is Greenland’s unlikely gateway: a small settlement set 190 kilometres inland at the head of a long fjord. Once a U.S. air base, it offers access to the ice sheet and guided excursions onto its immense white surface. Beyond town, tundra supports musk oxen and reindeer; nearby Russell Glacier reveals Greenland’s moving ice. Weather and distance shape every outing, so plan for conditions.