Ontario Canada, Niagara Falls Cruise from Toronto to Boston — 14 Days

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.

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.

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.

At Sea (At Sea)

Prince Edward Island, Canada

Charlottetown is a compact capital with a claim to Canadian history: delegates met here in 1864 to discuss Confederation. Brick storefronts, leafy streets and a working waterfront make its centre easy to explore on foot. See Province House, where the conference began, then browse Victoria Row’s boutiques and cafés. Beyond town, red-sand beaches and pastoral lanes reward a longer outing. Come for history; stay for Prince Edward Island’s pleasures.

Madeleine-Magdalen Islands, Canada

The Magdalen Islands rise from the Gulf of St. Lawrence, closer to Prince Edward Island than mainland Quebec. Red cliffs, long beaches and fishing villages keep the sea in view. Explore historic La Grave on Île du Havre-Aubert, where fishers’ cottages and galleries line the waterfront. Follow the coast for smoked herring, fresh lobster and views worth a slower day ashore.

Sydney NS, Canada

Sydney is the working harbour at the heart of Cape Breton Island, where Gaelic, Acadian and Mi’kmaq histories meet. Walk the waterfront to see the Big Fiddle, then browse downtown shops and cafés along Charlotte Street. Beyond town, the reconstructed Fortress of Louisbourg brings 18th-century French colonial life into striking focus. Use Sydney as a base for Cape Breton’s coastal roads, where ocean views and small communities invite an unhurried day.

Lunenburg NS, Canada

Few Canadian ports preserve their character as clearly as Lunenburg, a UNESCO-listed town on Nova Scotia’s South Shore. Painted wooden buildings climb steep streets above a working harbour, where fishing boats and schooners share the water. Visit the Fisheries Museum of the Atlantic, then look for Bluenose II, the celebrated schooner whose home port is Lunenburg. Explore the waterfront and its 18th- and 19th-century architecture on foot; the town rewards a slower pace.

Shelburne NS, Canada

Come ashore in Shelburne, where a broad natural harbour meets one of Nova Scotia’s best-preserved historic waterfronts. Founded in 1783 by Loyalists, the town still carries its early story along streets lined with heritage buildings. Visit the Shelburne County Museum, then explore the historic Dory Shop Museum. Its fishing boats tell a practical story of the region’s maritime heritage.

Eastport ME, USA

Eastport, on Maine’s Moose Island, faces Passamaquoddy Bay and the shores of New Brunswick. Here, powerful tides shape a working waterfront long tied to fishing and sardine canning. Explore the compact downtown’s galleries, historic buildings and Tides Institute & Museum of Art. Across the water, Campobello Island offers a striking reminder of how close Canada lies. Seasonal boat excursions may reveal seals, seabirds and whales.

Provincetown MA, USA

At Cape Cod’s outermost tip, Provincetown rewards a leisurely day ashore with sea air, history and a lively main street. Climb the Pilgrim Monument for a sweeping view, then explore Commercial Street’s galleries, cafés and independent shops. Whale-watching boats leave the harbor for waters frequented by humpbacks, while nearby dunes offer a quieter side of the Cape. Allow time for seafood and the town’s Portuguese-influenced culture; Provincetown is best enjoyed without rushing.

Boston, USA

Boston rewards visitors who like their history close at hand and their cities easy to explore. From the waterfront, follow the Freedom Trail to landmarks of the American Revolution, including Faneuil Hall. Beacon Hill’s brick streets, the Public Garden and North End cafés reveal distinct sides of the city. Make time for harbor views and New England seafood; Boston’s pleasures are as tangible as its past. Its museums and universities give the compact city a lively, modern edge.