Montreal, Quebec, Canada - Part French, part English, totally intriguing. Explore the cobblestone streets of lamp-lit Old Montreal; visit the tranquil Botanical Gardens; try your luck at the high-energy Casino de Montreal.

Quebec City, Quebec, Canada - Few places in North America are as steeped in history as Québec City, Canada. Older than Jamestown and founded before the Pilgrims landed at Plymouth Rock, it is the only city north of Mexico whose original fortifications remain intact. The Québec City historic district, a UNESCO World Heritage Site, is still home to religious orders and hospitals that date back to the 17th century. Its Place-Royale would look familiar to the explorer Samuel de Champlain, even with its modern attractions of gift shops and cafés. On the Plains of Abraham, you can walk the battlefield where, in 1759, the French forces under General Montcalm were decisively trounced by the British, led by General Wolfe.

Gulf Of St. Lawrence - A lighthouse on little St. Paul’s Island is a stark reminder of days gone by as you sail past this infamous old shipwreck site, known as the graveyard of the gulf, on your way through the Cabot Strait and into the Gulf of St. Lawrence. So huge is the gulf that half of Canada’s 10 provinces have a coastal connection to it. Perhaps that’s not surprising, considering that it’s the world’s largest estuary and fed all the way from the Great Lakes 1,200 kilometers (750 miles) away.

Charlottetown, Prince Edward Island - Despite its modest size, the city has an impressive number of Victorian buildings and great parks waiting to be explored. For Canadians, it is perhaps most famous as the Birthplace of Confederation. It was here, mostly at Province House, that an 1864 conference led to the creation of the Dominion of Canada. Prince Edward Island is linked to New Brunswick on the mainland of Canada by the 13-kilometer (eight-mile) Confederation Bridge that soars over the Northumberland Strait. A remarkable feat of engineering, the bridge opened in 1997 and is the longest in the world over icy waters.

Sites within downtown Charlottetown include the lovely Victoria Row, which becomes a pedestrian mall each summer, and other historic buildings, some of which are now museums. Nearby Prince Edward Island National Park is home to white-sand beaches and hiking and biking trails—plus fans can see the house and farm that inspired the beloved book Anne of Green Gables. During your visit, you can also learn about the daily lives, past and present, of residents on lighthouse and boat tours.

Sydney, Nova Scotia - So green and Gaelic is Cape Breton Island that Scotsman Alexander Graham Bell called it home for the last 37 years of his life. See why as you follow the scenic 184-mile-long Cabot Trail. Or tour to the Fortress of Louisbourg, meticulously restored to its 1744 mint condition.

Halifax, Nova Scotia - Located on a rocky inlet on the Atlantic Ocean, Halifax—Nova Scotia’s provincial capital—is defined by its maritime geography. It's a spirited mix of world-class history and nautical-themed museums alongside bunkers and fortresses that guarded the harbor, plus striking public art and sights, funky shops and excellent pubs serving up folk music (and good pints).

Bar Harbor, Maine, US - Located on Mount Desert Island in Maine, Bar Harbor is the quintessential New England coastal town. This picturesque and charming town is full of scenic and walkable streets lined with restaurants and boutiques. Dining on lobster is a must, as is a scoop or two at one of the town’s homemade ice cream shops. Boat tours explore the waters and islands that surround Bar Harbor, with seasonal opportunities to see wildlife—including whales—and lighthouses along the way.

Boston, Massachusetts - Before cruising out of Boston, take in the sights. Meander the streets to find historic wonders and modern neighborhoods; stores and restaurants with old-time character; and gracious green spaces as well as a beautiful waterfront. Take a trip back to the American Revolution—explore the Freedom Trail and see legendary figures come alive at buildings and attractions, including the Paul Revere House and Old South Meeting House, which are located in Lexington and Concord just outside Boston. Each Boston neighborhood has its own personality. Catch street performers in Cambridge’s Harvard Square, do a food tour of the North End’s Little Italy, and then admire the 19-century architecture of Beacon Hill.