The St. Lawrence, Maine & New England

North America's great bilingual city layers cobbled Old Montreal, its 17th-century stone buildings now home to some of the country's best restaurants, over a modern downtown built for a genuinely serious food and festival culture. The Lachine Canal's bike path and waterfront parks offer an easy afternoon on the water, while the Eastern Townships' vineyards, a short drive out, have quietly become a real source of Quebec ice wine and hybrid varietals. A round of golf on one of the island's historic courses and a stroll through a beach-lined riverfront park round out a city that rewards a slow wander as much as a fine meal.

The only walled city north of Mexico still standing in its entirety, Quebec City's Chateau Frontenac towers over a UNESCO old town of cobbled lanes and 17th-century stone houses that could pass, at a glance, for provincial France. Ile d'Orleans, a short drive across the bridge, supplies much of the region's cider, maple and cool-climate wine, while the city's own Nordic-style spas, built around riverside steam and plunge pools, draw on a wellness tradition as old as New France itself. A beach along the St Lawrence and a genuinely serious dining scene round out North America's most European city.

Widely considered the whale-watching capital of eastern Canada, Tadoussac sits exactly where the cold, deep Saguenay Fjord meets the St Lawrence, upwelling currents that draw belugas, minke, fin and the occasional blue whale within sight of the shore. The wooden Indian Chapel here, built in 1747, is the oldest wooden church still standing in North America, and the surrounding sand dunes and cliffs hold a genuinely rich variety of boreal birdlife. A round of golf on the town's small course rounds out one of Quebec's most naturally spectacular stops.

At the tip of the Gaspé Peninsula, where the St Lawrence finally gives way to open ocean, Gaspé is best known for what lies just offshore, the towering sea arch of Percé Rock and, beyond it, Bonaventure Island's colony of more than fifty thousand northern gannets, one of the largest and most accessible in the world. Forillon National Park's cliffs and forest trails ring the peninsula's tip, and the region's small fishing ports still turn out some of Quebec's best seafood. A dramatic, birdlife-rich edge of the province.

Canada's confederation was effectively born in this small Georgian capital, delegates met here in 1864 to first discuss uniting the colonies, a history the handsomely preserved Province House tells in full. Anne of Green Gables country lies a short drive across the island's red-soil farmland to Cavendish's dunes and beaches, while PEI's mussels and oysters, some of the best shellfish in Canada, anchor a genuinely excellent dining scene. Golf courses take full advantage of the island's rolling coastal terrain, and shorebirds crowd the red sandstone cliffs nearby. A small capital with an outsized role in Canadian history.

A narrow channel separates Cape Breton Island from mainland Nova Scotia here, spanned by a causeway that also, unusually, carries a lock to maintain water levels on either side. Fishing communities line both shores, their fortunes tied for generations to the strait's ice-free, deep-water access to the Atlantic. A short, characterful transit between two of Atlantic Canada's most storied coastlines.

A UNESCO World Heritage waterfront of saltbox houses painted in improbably bright colors, Lunenburg built and launched the Bluenose here in 1921, the racing schooner still pictured on the Canadian dime. Its shipbuilding heritage lives on in a working boatyard and a strong seafood scene built around the same scallop and haddock fleets that still work these waters. One of the best-preserved historic towns in Atlantic Canada, and one of the prettiest.

The easternmost city in the continental United States is the first place the country sees the sunrise each morning, a genuine point of local pride in a town built almost entirely around fishing and aquaculture. The Old Sow, the largest tidal whirlpool in the Western Hemisphere, churns in the bay just offshore, drawing porpoises and seabirds to the nutrient-rich water it stirs up. A small, salt-worn fishing town at the very edge of the map.

The gateway to Acadia National Park, where Cadillac Mountain's granite summit is, for part of the year, the first place in the United States to see the sunrise. Rockbound coastline and spruce forest ring a town built originally as a Gilded Age summer retreat, its grand "cottages" still visible along Frenchman Bay. A lobster dinner on the water, a round of golf at one of the region's classic courses, and some of the best birding on the Maine coast round out New England at its most dramatic.

The gateway to Acadia National Park, where Cadillac Mountain's granite summit is, for part of the year, the first place in the United States to see the sunrise. Rockbound coastline and spruce forest ring a town built originally as a Gilded Age summer retreat, its grand "cottages" still visible along Frenchman Bay. A lobster dinner on the water, a round of golf at one of the region's classic courses, and some of the best birding on the Maine coast round out New England at its most dramatic.

Maine's self-proclaimed lobster capital also holds the country's densest concentration of lighthouses, several visible from the harbor on a clear day. The Farnsworth Art Museum's collection of three generations of the Wyeth family, painters who made this coast their life's subject, is a genuine draw for art lovers well beyond Maine. A dining scene built almost entirely around the day's catch rounds out a small, working harbor town.

New England's unofficial food capital packs a genuinely serious dining and craft-brewing scene into a compact, cobblestoned Old Port, lobster rolls and oyster happy hours included. Portland Head Light, the oldest lighthouse in Maine, stands sentinel over a rocky shoreline that has changed remarkably little since it was built in 1791. A round of golf on the coastal links and some of the best birding on the Maine coast round out a small city that consistently punches above its weight.

America's most walkable big-city history lesson, the Freedom Trail's red brick line connects the sites of the Revolution in a couple of unhurried hours, from the Old North Church to the USS Constitution still afloat in the harbor. Boston Harbor's islands, a short ferry from downtown, hold surprisingly rich colonies of nesting seabirds for a major East Coast city. A round of golf at one of the region's historic clubs and a plate of the city's famous chowder round out a stop as dense with things to do as it is with history.