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 - 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. 

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.

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.

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