Canada & New England Cruises

Canada & New England in Windstar Style

Long before Columbus, Vikings crossed the Labrador Sea from Greenland to settle in L’Anse Aux Meadows. Centuries later, Portuguese fishermen, Basque whalers, French trappers, and English pilgrims would follow and discover a Promised Land where nature nurtures both body and soul. Here, where the sun first kisses North America, explorer Jacques Cartier found a place where “the scenery is indeed worth seeing and can’t be properly described in words.” The ravishing lighthouse-studded coast still inspires awe. Manna from the sea still delights palates. And small cruise ships like ours still ply these waters with a freedom denied to larger cruise ships.

New York City to Montreal - 12 Days

Head north from New York City to charming New England towns and coastal scenery that will take your breath away. Step into the living rooms of the Vanderbilts, Astors, and Morgans in Newport’s restored Gilded Age mansions. Witness the autumn spectacle of Acadia National Park from Bar Harbor. Discover the quaint, yesteryear charm of Charlottetown — inspiration for Anne of Green Gables. And watch for rare Blue and Beluga whales as you cruise the beautiful waters off the Gaspé Peninsula.

New York City to San Juan - 11 Days

This 11-day, southbound journey crosses 23 degrees of latitude to tropical islands where the average temperature difference between winter and summer can be less than 10 Fahrenheit degrees. Not long after Manhattan’s glowing skyline slips beyond the horizon, you turn south for Philadelphia, a city full of rich history. The elegant antebellum charm of Charleston greets you on your way to warmer breezes as you approach Bimini’s blue waters, a favorite fishing haunt and drinking destination for writer Ernest Hemingway. Swim along a quiet beach near Samana in the Dominican Republic, or search for rare birds and animals along the mangroves in Los Haitises National Park. Your final destination is just a day away among San Juan’s vibrantly painted buildings and the brooding, weathered walls of Castillo San Felipe del Morro. Nearby you’ll find sandy beaches and lively cantinas to help you completely forget about the encroaching winter months ahead.

Montreal to Boston - 10 Days

Quebec’s French-flavored history, Prince Edward Island’s anachronistic charm, the fusion of Acadian and Scottish cultures in Nova Scotia—each province distills its own blend of Old World and New, bucolic and urbane. Browse the shops and boulangeries along Quebec City’s picturesque Petit Champlain, the oldest street in North America. Fall under the spell of Charlottetown and Gaspe with their bright red covered bridges and Anne of Green Gables vibe, and Halifax with its lively pub culture and majestic Citadel. 

Combine an Inside Passage cruise stretching from Vancouver, British Columbia to Alaskan scenic fiords with a train and coach tour across British Columbia to the Canadian Rocky Mountains. Float among turquoise-tinged Alaskan ice floes in kayaks or Zodiacs with Windstar’s Signature Expedition guides, a team of highly skilled naturalists and wildness experts who assist and answer questions throughout the entire cruise. Sample Ketchikan’s tangy smoked salmon, rich Dungeness crab and frothy Alaska microbrews or wander among the largest collection of standing totem poles in the world. Shop for unique gifts and keepsakes in one-of-a-kind boutiques and modern galleries in Vancouver’s Gastown. Board the Rocky Mountaineer for a railway journey along the rushing Fraser River, verdant ranchlands, forgotten homesteads and precipitous canyons leading up and across North American’s Great Continental Divide. Soar skyward to the Sulphur Mountain summit and take in the panoramic splendors of Banff, sloping Mount Rundle, and distant jagged peaks. Strap in for a close-up tour of wilderness mountain peaks on a breathtaking helicopter tour. The journey eventually concludes after an overnight stay in Calgary, where you’ll find time to shop and ride to the top of Calgary Tower with countless sparkling city lights stretching from Alberta’s flat eastern prairies to rolling western foothills and peaks traced in sunset afterglow.

Reykjavik to New York City - 15 Days

Cross the North Atlantic from Iceland’s dramatic landscapes to the rocky shores of Southeast Canada and New England. Along the way, visit places beyond the reach of larger ships like the UNESCO sites of Red Bay and L’Anse Aux Meadows with their whaling and Viking pasts, and tiny Acadian villages like Bonne Bay in the midst of Gros Morne National Park’s beauty. Fill your camera’s memory cards in scenic Acadia National Park and picturesque Peggy’s Cove. Watch for whales in the wildlife-rich Cape Cod Canal (another place inaccessible to larger ships). Take in Norse ruins, lobster bakes and fiddle music that speaks to the soul.

Embark on your Atlantic adventure in Copenhagen, a fairytale city filled with palaces, parliament, and the palate-pleasing tastes of Tivoli Gardens before cruising to breathtaking fjords in Geiranger, Norway. Bergen brings an opportunity to overnight and visit colorful Bryggen, the old Hanseatic wharf and UNESCO site. In Hellesylt, a waterfall divides the UNESCO town in two, Sunnylvsfjorden boasts restored hillside farmhouses and incredible hiking. Enjoy the Art Nouveau city of Alesund and explore Lerwick, the Shetland Islands’ only town with abundant marine life, tiny ponies and windswept cliffs. Kirkwall, in Scotland’s Orkney Islands, takes you back to a 5,000-year-old village, offers a chance to sample peat-distilled whisky, and visit the UNESCO site of the Ring of Brodgar, dating back to 2700 B.C. Visit the traditional turf roof villages of Torshavn and shop for distinctive knit wool sweaters in Denmark’s Faroe Islands. Iceland brings the eclectic architecture and vibrant art scene of Reykjavik, the glaciers and calderas of Snæfellsjokull National Park, and Heimaey Island’s modern-day Pompeii. Cross the Labrador Sea to discover Newfoundland, Canada with one of North America’s oldest settlements in St. John’s, an 11th century Viking settlement in L’Anse Aux Meadows, and the 10,000 year old glacier-carved Bonne Bay teaming with moose, caribou, Arctic hare and ptarmigan. Grab a donair (meat-filled pita) in Halifax. Then set sail for New England, visiting Acadia National Park, near Bar Harbor, Maine, the marine life rich Cape Cod Canal, and finally New York City with its iconic sites from the Empire State Building and Times Square to Central Park and the Statue of Liberty.

Montreal to San Juan - 23 Days

The sugary, cinnamon sweetness of a doughy beavertail pastry overwhelms your taste buds as you stroll along the cobblestones throughout Old Montreal’s Parisian-themed shops, cafes and brasseries. Relax on a scenic horse-drawn carriage ride or savor buttery-rich lobster among Bar Harbor’s brightly painted boutiques and galleries. Amble along New York’s Central Park serpentine paths, or take in the skyline from a departing Staten Island Ferry bound for the Statue of Liberty. Sample regional wines from Long Island, Finger Lakes, and Hudson River Valley in a Manhattan wine shop. Brush the gray armor plating of USS Wisconsin’s imposing 16-inch guns on Virginia’s Elizabeth River, or admire more than 450 fragrant rose flowers at the Norfolk Botanical Garden. Then relax and break out your shorts and light cotton shirts for the sea days leading up to the warm beaches and mangrove mysteries in Bimini and Samaná. Your journey culminates in San Juan’s Old City, within walking distance of El Morro’s scarred fortress walls. Wander the storied streets where traders plied their wares or made idle chatter about the tobacco trade and worrisome pirates. Order a potent rum drink at a raucous neighborhood pub or request a fruit cocktail from a quiet, sundrenched table overlooking the harbor. It’s a perfect way to cap the unforgettable experiences on this extensive Atlantic Seaboard odyssey.

Start your journey in Reykjavik, the world's most northerly capital, where 24-hours of summer sunlight extend your chance to explore the city’s eclectic architecture and soak in the Blue Lagoon. Grundarfjordur offers the glaciers and calderas of Snæfellsjokull National Park and Heimaey Island is the site of an eruption that is considered a modern-day Pompeii. Cross the Labrador Sea to discover Newfoundland, home to some of North America’s oldest settlements and the 10,000-year-old glacier-carved Bonne Bay home of plentiful moose and caribou. Shop the boardwalk in Halifax, then, set sail for New England, visiting Acadia National Park, near Bar Harbor, Maine, the Cape Cod Canal, and bustling New York City. Explore the Vanderbilt mansions and sample fresh seafood in Newport, Rhode Island and embark on the same shores as the Mayflower in Provincetown, Massachusetts. Transit the Canso Canal and head to picturesque Charlottetown, the inspiration for Anne of Green Gables on Prince Edward Island. In Quebec, enjoy remote wilderness and North America’s largest gannet colony near Perce Rock in Gaspé, overnight in beautiful and historic Quebec City, and finish your voyage in Montreal, the creative capital of Canada with lovely terraced cafés.

Begin your 30-day, 3,000+-mile journey from Canada to the Caribbean in Montreal, the creative capital of Canada. An overnight in Quebec City allows time in one of North America’s oldest and most beautiful cities. Explore Gaspé’s wilderness area and Charlottetown’s waterside boardwalks. Transit the Canso Canal to Halifax with its 200-year-old fishing village. Bar Harbor brings the beauty of Acadia National Park and Provincetown is the proud home to the Mayflower landing. Watch for wildlife in Cape Cod Canal before sailing into Newport, the host city of America’s Cup. New York City is next with its 5 famous boroughs and iconic attractions. Overnight in Philadelphia and visit Charleston’s celebrated City Market. Then it’s off to the Caribbean for Bimini’s beaches (Hemingway’s favorite escape), Samana’s untamed Los Haitises National Park, San Juan’s Spanish El Morro fortress and Vieques’ 20+ beaches. Discover Roseau’s bubbly waters of Champagne Beach and Morne Trios Pitons National Park. Take in St. Lucia’s majestic volcanoes, and the “Isle of Spice” in the gorgeous city of St. George’s. End your magical adventure in Bridgetown’s Harrison’s Cave.

Copenhagen to Montreal - 37 Days

Your Atlantic adventure begins in Copenhagen, a fairytale city and home of delightful Tivoli Gardens, on to overnight in Bergen and visit UNESCO site Bryggen, the old Hanseatic wharf. Cruise to the breathtaking fjords in Geiranger, Norway and to the UNESCO town of Hellesylt. Tour the Art Nouveau city of Alesund and Lerwick, the only town in the Shetland Islands. From Kirkwall, you will have a chance to visit the UNESCO site of the Ring of Brodgar, dating back to 2700 B.C. Have your camera ready to capture the traditional turf roof villages of Torshavn and see the impressive glaciers and calderas of Snæfellsjokull National Park, and Heimaey Island’s modern-day Pompeii. Cross the Labrador Sea to Newfoundland, home to some of North America’s oldest settlements, 10,000 year-old glacier-carved Bonne Bay and a large population of moose and caribou. Visit Acadia National Park, near Bar Harbor, Maine, transit the marine life rich Cape Cod Canal, and explore the famous Vanderbilt mansions in Newport. Sample fresh seafood in Newport, Rhode Island and embark on the same shores as the Mayflower in Provincetown. Transit the Canso Canal and head to the picturesque Prince Edward Island town of Charlottetown. In Quebec, enjoy the remote wilderness and French-styled lobster of Gaspé, savor an overnight in the beautiful and historic Quebec City, and finish your voyage in Montreal, a UNESCO City of Design with terraced cafés serving Kamouraska lamb, Arctic char and signature poutine.

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