Canada, New England & Iceland

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.

Portland, Maine, is America’s most exciting small food city, perched on a Casco Bay peninsula where the Old Port’s brick-and-granite streets house more restaurants per capita than nearly any U.S. city, fueled by legendary Maine lobster and Gulf oysters. Must-dos include a lobster roll on the working waterfront, browsing the Portland Museum of Art’s Winslow Homer collection, and a ferry ride to Casco Bay’s car-free islands. Visit September and October for New England’s spectacular fall foliage and the finest weather.

Sydney, on Cape Breton Island in Nova Scotia, is a charming harbour city where Scottish-Acadian heritage meets raw Atlantic beauty, serving as the gateway to the legendary Cabot Trail — one of the world's most spectacular coastal drives. Visitors should savour the island's renowned seafood chowder and traditional oatcakes while exploring the colourful waterfront boardwalk. The peak season stretches from late June through October, when autumn's fiery foliage transforms the highlands into a tapestry of crimson and gold.

Saint Pierre and Miquelon is France's last territory in North America, a fog-wrapped archipelago off Newfoundland where croissants, crêpes, and the euro coexist with cod fishing and Prohibition-era history. Must-dos include exploring the rum-running Heritage Museum, dining on fresh cod and French wines, and visiting the haunting cemetery on Île aux Marins. June through September offers the best weather for this improbable outpost of French culture.

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.

Ísafjörður is the cultural and historical capital of Iceland's remote Westfjords, a dramatic fjord-side settlement where centuries of fishing heritage meet stark Arctic grandeur. Visitors should not miss the communal seafood feast at Tjöruhúsið restaurant and a journey to the surreal red sands of Rauðasandur beach near Patreksfjörður. The optimal visiting window is June through August, when nearly perpetual daylight illuminates the encircling mountains and the town's vibrant cultural calendar reaches its peak.

Akureyri, the cultural capital of northern Iceland, sits at the head of the majestic Eyjafjörður and serves as a gateway to some of the island's most dramatic landscapes, including the thundering Goðafoss waterfall, the volcanic wonderland of Lake Mývatn, and Europe's most powerful cascade at Dettifoss. Visitors should not miss the excursion to Mývatn's geothermal pools and the tasting of traditional *hangikjöt* smoked lamb at a harbourside restaurant. The ideal season to visit is June through August, when the midnight sun bathes the fjord in endless golden light and the botanical gardens reach their luminous peak.

Seyðisfjörður is a remote artist colony and historic port tucked into a dramatic fjord on Iceland's eastern coast, renowned for its nineteenth-century painted timber houses, the iconic Blue Church, and a thriving creative scene anchored by the annual LungA festival. Visitors should not miss the fjord approach by sea and a day trip to Dettifoss, Europe's most powerful waterfall. The prime visiting season is June through August, when the midnight sun bathes the fjord in golden light and cruise lines including Viking, Celebrity, and Holland America call at this intimate harbour.

Djúpivogur is an intimate Icelandic fishing village on the eastern coast where thirty-four stone egg sculptures line the harbor, Vatnajökull glacier dominates the horizon, and puffin colonies nest on nearby Papey island. Visit June through August via Seabourn or Viking for reindeer sightings, glacier views, and the quiet eastern Iceland that rewards travelers who venture beyond the Golden Circle.

Heimaey is Iceland's volcanic island where the dramatic 1973 eruption story, the world's largest puffin colony of one million breeding pairs, and the children's annual puffling rescue create one of the North Atlantic's most extraordinary port experiences. Visit May through August via Lindblad or Windstar for Eldfell volcano hikes, the Eldheimar Museum's excavated homes, and the harbor approach through a channel literally reshaped by eruption.

Reykjavik, the world's northernmost capital, distils the entire improbable beauty of Iceland into one compact, creatively charged city. The soaring basalt columns of Hallgrímskirkja dominate a skyline of primary-coloured rooftops, while the Harpa Concert Hall shimmers beside the harbour like a captured aurora. Day trips from the city unlock the Golden Circle's geysers and Geysir hot spring, the black sand beaches of Vík, and the ethereal glacier lagoon at Jökulsárlón. Geothermal pools — from the legendary Blue Lagoon to intimate neighbourhood hot pots — offer warmth year-round. June and July bring the bewitching midnight sun.

Grundarfjörður is a tiny Icelandic fishing village dominated by the iconic Kirkjufell mountain on the Snæfellsnes Peninsula — Jules Verne's gateway to the Earth's center. Visit June through August via Seabourn or Windstar for the peninsula's compressed geological wonders including glacier volcanoes, black sand beaches, and seal colonies, or September through March for the chance to see Kirkjufell crowned by northern lights.

Qaqortoq is southern Greenland's largest town, where brightly painted houses climb above a fjord harbour amid open-air stone sculptures and Norse ruins. Must-do experiences include visiting the Hvalsey Norse church ruins, soaking in the Uunartoq hot springs surrounded by icebergs, and tasting Arctic char and musk ox. June through September offers the accessible season, with July and August warmest for fjord exploration.

Nanortalik, Greenland's southernmost town, sits amid fjords of staggering granite walls and drifting icebergs at the edge of the inhabitable Arctic. Must-dos include boat excursions to Tasermiut Fjord's 1,500-meter granite spires, visiting the open-air museum of Inuit heritage, and tasting traditional Greenlandic cuisine. July through September offers the only navigable window for visiting.

St. Anthony sits at Newfoundland's northern tip, serving as the gateway to Iceberg Alley, whale-watching waters, and the UNESCO-listed Viking settlement at L'Anse aux Meadows. Must-dos include watching thousand-year-old icebergs drift past and exploring North America's only authenticated Norse site. June and July offer peak iceberg and whale season.

Fiskardo is the only village on Kefalonia to survive the 1953 earthquake, preserving a stunning Venetian-era waterfront of pastel townhouses overlooking a harbor with views to Homer's Ithaca across the channel. Must-dos include dining on fresh fish at a harbor terrace, swimming at Emblisi Beach, and tasting local Robola wine. May through October offers ideal conditions, with September being especially pleasant.

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.

Cap aux Meules, 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 Scenic Ocean Cruises 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.

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.

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.