Toronto - Boston

Toronto is Canada's most multicultural metropolis, where over 200 languages, the ROM's Libeskind crystal, Frank Gehry's AGO redesign, and neighborhoods spanning every cuisine on Earth create one of North America's most rewarding and underestimated cities. Visit September via Viking for the Toronto International Film Festival, waterfront island escapes, and the revelation that Canada's financial capital harbors cultural diversity rivaling any city on the continent.

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.

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.

Tadoussac is a historic village at the mouth of Canada's Saguenay Fjord, where cold river waters meeting the St. Lawrence create one of the world's premier whale-watching destinations with up to 13 species including belugas, fin whales, and occasional blue whales. Must-dos include a Zodiac whale-watching excursion, kayaking the dramatic Saguenay Fjord, and visiting North America's oldest wooden church. Visit August or September for peak whale diversity and autumn foliage.

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.

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.

Gaspe, Canada, offers an authentic North American experience where stunning natural landscapes meet communities of genuine character. Visitors should explore the surrounding wilderness and sample the honest, locally sourced cuisine that defines the region. The ideal visiting period is May through October, when the climate is at its most welcoming for outdoor exploration. Cruise lines including Seabourn feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

The Îles de la Madeleine are a windswept Acadian archipelago in the Gulf of St. Lawrence, defined by dramatic red sandstone cliffs, pristine beaches, and a lobster-fishing culture that shapes daily life. Must-dos include tasting fresh lobster and smoked herring, kayaking beneath the sculpted red cliffs, and visiting during harp seal pupping season. June–September offers the best weather, while late February–March brings the extraordinary harp seal pup encounter on the ice floes.

Charlottetown is the Birthplace of Canadian Confederation and Prince Edward Island's gracious Victorian capital, where Province House witnessed the nation's founding and the world's longest-running annual musical has played since 1965. Visit June through October via Cunard or Regent Seven Seas for legendary PEI oysters and lobster, red sand beaches, and the Green Gables landscape that inspired one of literature's most beloved heroines.

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.

Bar Harbor, United States, offers an authentic North American experience where stunning natural landscapes meet communities of genuine character. Visitors should explore the surrounding wilderness and sample the honest, locally sourced cuisine that defines the region. The ideal visiting period is May through October, when the climate is at its most welcoming for outdoor exploration. Cruise lines including Norwegian Cruise Line feature this port on their most compelling itineraries. Whether you have a few hours or a full day, the port rewards exploration at every pace and in every direction.

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.