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.

Montreal to New York City - 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.

Montreal to Boston - 11 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. 

Reykjavik to Montreal - 14 Days

Float past turquoise-tinged ice floes as you experience Greenland’s remote southern fjords and villages prior to visiting the scenic coasts of Newfoundland, Nova Scotia and New England during this 14-day cruise along the North Atlantic’s most pristine and picturesque shorelines. Survey towering icebergs and catch glimpses of fin, killer, and pilot whale pods, along with native seabirds like fulmars, great cormorants and black-legged kittiwakes during your Denmark Strait crossing and subsequent cruise past glacier-etched outcroppings throughout Prince Christian Sound. Embark on an iceberg safari beyond Narsaq. Drift close to towering, picture-perfect ice blocks and calving glaciers in Sermilik Fjord. Sample smoky onion soup, duck filets drenched in wild berry sauce and other authentic French cuisine on a St. Pierre and Miquelon foodie walking tour off the coast of Newfoundland. Ride in an open carriage along the storied Carriage Trails in Acadia National Park and experience the American wilderness the same way visitors did a century ago.

New York City to San Juan - 11 Days

Venture from the cosmopolitan Big Apple to warm Bermuda beaches and the picturesque Caribbean shorelines of Grenada, St. Barts, St. Kitts, and the British Virgin Islands during this 11-day cruise. Kayak amid gliding sea turtles and radiant tropical fish, explore pastel-hued Bermuda shops, and dine on traditional codfish dishes, spiny lobster and seared tuna steaks during an overnight stay in Hamilton. Sample aromatic nutmeg and rich chocolates on a flavorful Grenada spice factory tour. Measure your progress on a St. George’s foodie and history walking with frosty Piña Coladas, citrusy painkillers, and varied rum punches during your overnight port stay. Shop for one-of-a-kind jewelry or distinctly classic island casual wear at St. Bart boutiques in Gustavia. Sunbathe and snorkel near the golden sands and green hills defining iconic South Friars Bay near Basseterre. Dance, dine and savor the company of good friends and attentive crew at Windstar’s exclusive Signature beach party on Virgin Gorda.

Venture into the lesser-known coastlines and communities of Greenland, Canada and New England during this remarkable 25-day cruise crossing the North Atlantic. Admire fractured glaciers, ivory ice fields and drifting ice floes on a day of scenic cruising in Greenland’s remote and picturesque Prince Christian Sound. Sample grilled wolf fish, dried salted cod and tender musk ox meat amid stacked crab pots, fish-drying racks and brightly painted houses in Qaqortoq, Nanortalik and Narsaq in Greenland. Wander the grounds of a 1,000-year-old Norse settlement near St. Anthony, and tour sod buildings identical to those that sheltered early settlers from harsh Newfoundland winters centuries ago. Walk among weathered French and British artillery artifacts at National Battlefields Park, or sip your way through Quebec City’s outstanding microbreweries on a delicious walking tour in a thriving downtown community. Settle back in a horse-drawn carriage as you trace the famous Carriage Trails of Acadia near Bar Harbor, Maine.

Depart from New York and cruise along the East Coast prior to exploring Bermuda and the Caribbean’s Leeward Islands in detail during this 21-day escape. Snorkel above Bermuda’s most popular shipwrecks—a Confederate paddle wheeler and a four-masted sailing ship—near Hamilton, then dine on juicy swordfish, decadent lobster and seared tuna steaks prior to overnight stays there and in St. George’s. Sail a swift catamaran along the scenic leeward side of St. Barts near Gustavia. Roll past rural cane fields and rustic country farms during a guided ATV outing near Basseterre on St. Kitts. Dance, dine and celebrate at a Windstar Signature Beach Party with friends and crew at Virgin Gorda. Kayak from tangled mangroves to the vast expanse of open blue sea on a guided exploration of Puerto Rico’s Vieques coastline. Soar among colorful rainforest birds and verdant tropical trees during a canopy zipline adventure on Pigeon Island or take a leisurely-paced seaside painting class at St. Lucia’s picturesque Rodney Bay Village.

Thank You!

We'll send you the latest deals to your email.

Click here to view our current special offers.