New England, New France & Newfoundland : Corner Brook

Boston is America's revolutionary birthplace and intellectual capital, a supremely walkable city where the Freedom Trail connects sixteen historic sites past Italian North End bakeries and Beacon Hill's gaslit streets. Must-do experiences include walking the Freedom Trail, eating a lobster roll at the Union Oyster House, and exploring the Isabella Stewart Gardner Museum. September and October bring peak fall foliage; spring brings the Marathon and blooming gardens.

Eastport, Maine, United States is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Princess Cruises. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is May through September, when mild temperatures and long days favor unhurried exploration.

Halifax, the historic capital of Nova Scotia, is a refined Atlantic port where centuries of maritime heritage meet a flourishing culinary scene anchored by Digby scallops, donairs, and one of North America's oldest farmers' markets. Visitors should not miss the star-shaped Citadel Hill and the harbourfront boardwalk's constellation of galleries and tasting rooms. The ideal season stretches from late June through October, when autumn's blazing foliage transforms the entire province into a masterwork of colour and the cruise terminal welcomes the world's finest vessels.

St. John's is North America's oldest English-founded city, a colourful Newfoundland harbour capital where Jellybean Row houses climb steep hills, Marconi received the first transatlantic wireless signal, and icebergs drift past the harbour mouth each spring. Must-dos include climbing Signal Hill for Atlantic panoramas, the screech-in cod-kissing ceremony, and hiking to Cape Spear — the continent's easternmost point. Visit July or August for warm weather and iceberg season.

Saint-Anthony perches at Newfoundland's northern tip, where massive Greenland icebergs drift past headlands and humpback whales chase capelin through frigid waters. Must-dos include iceberg boat tours (May-July), visiting the Grenfell Historic Properties, and day-tripping to L'Anse aux Meadows — the Viking settlement predating Columbus by five centuries. The best season spans June through September, with May-July ideal for iceberg viewing and July-August for whale watching.

Corner Brook sits on Newfoundland's west coast at the head of the Bay of Islands, framed by the Long Range Mountains and steeped in maritime history dating to Captain Cook's 1767 survey. Must-dos include visiting nearby Gros Morne National Park, tasting pan-fried cod tongues, and taking in the bay panorama from Cook's monument. July through September offers the best weather, with autumn foliage adding dramatic color.

Havre-Saint-Pierre, Quebec, Canada is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Silversea. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is June through August, when summer months bring the warmest temperatures and longest days.

Baie-Comeau, Quebec, Canada is a distinctive port city where deep cultural heritage meets authentic local atmosphere, featured on itineraries by Seabourn. Must-do experiences include walking the historic center to experience the layered architectural heritage, and seeking out the regional culinary traditions at a locally favored establishment away from the port area. The optimal time to visit is May through September, when mild temperatures and long days favor unhurried exploration.

The Saguenay is a glacially carved fjord of Norwegian grandeur hidden in Quebec, where three-hundred-meter cliffs plunge into waters hosting the world's southernmost beluga whales alongside blue whales, fins, and humpbacks. Visit September through October via Cunard or Azamara for autumn-color fjord transits, world-class whale-watching at Tadoussac, and one of Canada's most spectacular and least-expected natural treasures.

Quebec City is North America's only walled city, a UNESCO treasure where 400 years of French colonial architecture crown a St. Lawrence promontory beneath the iconic Château Frontenac. Visit September through October via Cunard or Seabourn for autumn foliage transforming stone ramparts, elevated Québécois terroir cuisine, and the singular experience of genuine Old World atmosphere on a continent that rarely provides it.

Montreal is the world's second-largest francophone city, set on an island in the St. Lawrence River where French colonial heritage meets North American energy and one of the continent's most exciting food scenes. Must-dos include visiting the stunning Basilique Notre-Dame, eating smoked meat at Schwartz's and bagels at St-Viateur, and exploring the Plateau's bohemian streets. June through September offers peak festival season, including the world's largest jazz festival.