Day 1 Boston, Massachusetts, United States

There's history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone streets. But to Bostonians, living in a city that blends yesterday and today is just another day in beloved Beantown.

Day 3 Sydney, Nova Scotia, Canada

If you come directly to Cape Breton via plane, ferry, or cruise ship, Sydney is where you'll land. If you're seeking anything resembling an urban experience, it's also where you'll want to stay: after all, this is the island's sole city. Admittedly, it is not the booming center it was a century ago when the continent's largest steel plant was located here (that era is evoked in Fall on Your Knees, an Oprah Book Club pick penned by Cape Bretoner Anne-Marie MacDonald). However, Sydney has a revitalized waterfront and smattering of Loyalist-era buildings that appeal to visitors. Moreover, it offers convenient access to popular attractions in the region—like the Miner's Museum in nearby Glace Bay (named for the glace, or ice, that filled its harbor in winter), the Fortress at Louisbourg, and beautiful Bras d'Or Lake.

Day 4 Charlottetown, Prince Edward Island, Canada

Designated as the Island capital in 1765, Charlottetown is both PEI's oldest and largest urban center. However, since the whole "metropolitan" area only has a population of about 65,000, a pleasing small-town atmosphere remains. The city is a winner appearance-wise as well. Peppered with gingerbread-clad homes, converted warehouses, striking churches, and monumental government buildings, Charlottetown's core seems relatively unchanged from its 19th-century heyday when it hosted the conference that led to the formation of Canada. The city is understandably proud of its role as the "Birthplace of Confederation" and, in summer, downtown streets are dotted with people dressed as personages from the past who'll regale you with tales about the Confederation debate.

Day 5 Cap-aux-Meules, Magdalen Islands, Québec, Canada

Day 6 Corner Brook, Newfoundland and Labrador, Canada

Newfoundland's fourth-largest city, Corner Brook is the hub of the island's west coast. Hills fringe three sides of the city, which has dramatic views of the harbor and the Bay of Islands. The town is also home to a large paper mill and a branch of Memorial University. Captain James Cook, the British explorer, charted the coast in the 1760s, and a memorial to him overlooks the bay.The town enjoys more clearly defined seasons than most of the rest of the island, and in summer it has many pretty gardens. The nearby Humber River is the best-known salmon river in the province, and there are many kilometers of well-maintained walking trails in the community.

Day 7 Saint Pierre, Saint Pierre and Miquelon

By heading almost due east from Cap-aux-Meules in Canada, it is possible to reach France in about one day's worth of steaming! With barely 6,000 inhabitants living on tiny St. Pierre, it is the smallest French Overseas Collective. The residents of St. Pierre are predominantly descendants of Normans, Basque and Bretons and the French spoken is closer to Metropolitan French than to Canadian French. Although Basque is not spoken any longer, the influence is still felt through sport and a Basque Festival. Interestingly, this small island has two museums in part dedicated to the Prohibition. The Musée Heritage is St. Pierre's newest museum with a focus on medical artefacts from the 19th and 20th century. Another claim to fame is a guillotine, the only one ever used in North America. In this quirky village it is easy to find the Post Office; just look for the clock tower shaped like a praying monk.

Day 8 Saint-John's, Newfoundland and Labrador, Canada

Old meets new in the province's capital (metro-area population a little more than 200,000), with modern office buildings surrounded by heritage shops and colorful row houses. St. John's mixes English and Irish influences, Victorian architecture and modern convenience, and traditional music and rock and roll into a heady brew. The arts scene is lively, but overall the city moves at a relaxed pace.For centuries, Newfoundland was the largest supplier of salt cod in the world, and St. John's Harbour was the center of the trade. As early as 1627, the merchants of Water Street—then known as the Lower Path—were doing a thriving business buying fish, selling goods, and supplying alcohol to soldiers and sailors.

Day 10 Halifax, Nova Scotia, Canada

Surrounded by natural treasures and glorious seascapes, Halifax is an attractive and vibrant hub with noteworthy historic and modern architecture, great dining and shopping, and a lively nightlife and festival scene. The old city manages to feel both hip and historic. Previous generations had the foresight to preserve the cultural and architectural integrity of the city, yet students from five local universities keep it lively and current. It's a perfect starting point to any tour of the Atlantic provinces, but even if you don't venture beyond its boundaries, you will get a real taste of the region.It was Halifax's natural harbor—the second largest in the world after Sydney, Australia's—that first drew the British here in 1749, and today most major sites are conveniently located either along it or on the Citadel-crowned hill overlooking it. That's good news for visitors because this city actually covers quite a bit of ground.Since amalgamating with Dartmouth (directly across the harbor) and several suburbs in 1996, Halifax has been absorbed into the Halifax Regional Municipality, and the HRM, as it is known, has around 415,000 residents. That may not sound like a lot by U.S. standards, but it makes Nova Scotia's capital the most significant Canadian urban center east of Montréal.There's easy access to the water, and despite being the focal point of a busy commercial port, Halifax Harbour doubles as a playground, with one of the world's longest downtown boardwalks. It's a place where container ships, commuter ferries, cruise ships, and tour boats compete for space, and where workaday tugs and fishing vessels tie up beside glitzy yachts. Like Halifax as a whole, the harbor represents a blend of the traditional and the contemporary.

Day 12 Boston, Massachusetts, United States

There's history and culture around every bend in Boston—skyscrapers nestle next to historic hotels while modern marketplaces line the antique cobblestone streets. But to Bostonians, living in a city that blends yesterday and today is just another day in beloved Beantown.