Canada & New England in Yacht Style
It's a match made in heaven...
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 yacht like ours still ply these waters with a freedom denied to larger ships.
Which voyage will you embark on first?
Terms and Conditions Apply
*All prices listed on this website are in Australian Dollars (AUD). Prices shown are cruise only indicative per person, based on twin occupancy inclusive of taxes & port charges. Pricing and availability are dynamic and subject to change at any time. Cabin category & configuration, occupancy, promotional availability, and supplier conditions at the time of booking may impact pricing and availability.
All-In Package – Includes beverages, Wi-Fi, and service charges. Beverages: Includes all domestic and imported beer, up to 33 varieties of wine or sparkling wine by the glass, plus cordials, liqueurs, aperitifs, cocktails, and mini-bar items. Cocktails are based on house and select brands, with guests able to choose from a selection of more than 40 liquors. Wi-Fi: Available in most public areas, staterooms, and suites, depending on the yacht’s course and position. Connectivity may vary. Service Charges: All hotel and beverage service fees are included. If beverages are purchased à la carte, an 18% gratuity (subject to change) will be added to the purchase price. All-In may be included as part of the promotional offer or maybe be purchased at an additional cost. Please check at time of booking to discuss applicable promotions suitable for your cruise reservation.
Airfares from Australia, pre- and post-cruise accommodation or transfers, shore excursions can be added to your cruise booking at an additional cost by Windstar Australia.
Cruise itineraries are not guaranteed and may be changed or cancelled at any time by Windstar Cruises. Special offers apply to new bookings only. Change and cancellation conditions apply and will be advised at the time of booking.
Experience Your Next Getaway in Casual Elegance!
Windstar Cruises operates a fleet of small casually elegant yacht known for their intimate yacht style experience and unique voyages to the world’s best small ports and hidden harbours. Its seven yachts carry fewer than 350 privileged guests and cruise to 52 nations, calling at 155 ports throughout Europe, the South Pacific, the Caribbean, and Central America. In 2020, Windstar worked to expand and refurbish their three power yachts, adding additional dining, a range of new suites as well as a whole host of upgraded or additional amenities. Windstar Cruises is named World’s Best Small Ship Cruise Line by Condé Nast Traveler 2022.
Star Collector Voyages combine some of our most popular itineraries for a more in-depth exploration of each region. Featuring longer voyages of 14+ days and few repeated ports, take advantage of your time here and unpack only once. Travel the world spending more time sampling exotic cuisines, immersing yourself in new cultures, and discovering perspectives that open your heart and return home with a soul fulfilled.
All Star Collector Voyages feature FREE daily laundry, so you can travel light and come home with a well-travelled suitcase and one less chore.
See Even More of the world aboard a Casually Elegant Private Yacht
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Experience Your Next Getaway in Casual Elegance!
Call 1300 749 875 or talk to your Travel Agent to get onboard.
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11 NIGHTS - SOUTHEAST CANADIAN EXPLORATIONS
- Montreal to Boston (or vice versa) -
- Witness the vibrant beauty of the fall foliage along the East Coast of the United States & Canada
- Catch the attractions of Quebec City, a UNESCO site
- See how many of Charlottetown's 11 National Sites of Canada you find and understand the inspiration for Anne of Green Gables
- Plan extra time in historic Boston, one of America's oldest cities and home of the JFK Library
- Try the unique cuisine of Montreal - poutine, Arctic char and Kamouraska lamb
- Enjoy the New England charm and lovely Victorian-era architecture in Portland
- Learn the role vibrant Halifax played when the Titanic sank
From $6,486*pp
2026 Departures: 14 Sep, 9 Oct
2027 Departures: 16Sep, 11 Oct
14 NIGHTS - GREENLAND: NORTH ATLANTIC ODYSSEY
- Reykjavik to Montreal -
- See dramatic and rare landscapes of some of the northernmost ports of call
- Learn about Greenland’s native Inuit culture
- Soak in the 100⁰ natural hot springs at Uunartoq near Qaqortoq
- Appreciate the scenic cruising in impressive Prince Christian Sound, open only three months a year
- Stroll the streets of UNESCO site Lunenburg with its unique architecture
- Have your binoculars out to look for the seabirds, seals and other wildlife around St. Pierre & Miquelon
- With its reputation for great dining, Portland’s Old Port district offers a variety of warehouses converted to restaurants
From $8,793*pp
2026 Departures: 31 Aug
24 NIGHTS - STAR COLLECTOR: AUTUMN IN NEWFOUNDLAND AND NEW ENGLAND
- Boston to Montreal -
- - Pack light with complimentary daily laundry service.
-Soak up history as you walk the cobblestone streets of Old Quebec, Boston’s Freedom Trail, and the Fortress of Louisbourg. And add to your UNESCO life list as you tick off nearly half a dozen ranging from America’s first Viking outpost to unspeakably beautiful Gros Morne National Park.
- Fall in love with Gallic culture and Old World streets lined with bistros, boutiques, and boulangeries, and spend your old Euros in St. Pierre & Miquelon, the last remaining French territories in North America.
- Visiting St. John's in the fall offers a delightful blend of vibrant autumn colors and cultural experiences, from exploring Signal Hill to enjoying the local arts scene.
- In St. Anthony and Bonne Bay, a small ship exclusive port, you can immerse yourself in breathtaking landscapes, discover Viking history, and savour seasonal seafood while taking in the stunning coastal views.
From $13,873*pp
2026 Departures: 14, 25 Sep
2027 Departures: 16 Sep
21 NIGHTS - STAR COLLECTOR: NORTH ATLANTIC EXPLORER
- Reykjavik to Montreal -
- - Pack light with complimentary daily laundry service.
- Learn about Greenland’s native Inuit culture
- Sample the unique cuisine of Montreal which includes poutine
- Soak in the 100⁰ natural hot springs at Uunartoq near Qaqortoq
- Overnight in Seydisfjordur, with its colorful historic houses imported from Norway by wealthy merchants at the turn of the 20th century
- Have your binoculars out to look for the seabirds, seals and other wildlife around St. Pierre & Miquelon
- Sail past Surtsey Island, the youngest place on earth, created by an eruption in 1963
- Pack light with complimentary daily laundry service
From $14,124*pp
2026 Departures: 24 Aug
2027 Departures: 26 Aug
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25 NIGHTS - STAR COLLECTOR: GREENLAND FJORDS, CANADIAN MARITIMES
- Reykjavik to Montreal -
- See dramatic and rare landscapes of some of the northernmost ports of call and have your binoculars out to look for the wildlife
- Learn about Greenland’s native Inuit culture
- Walk around the brightly painted houses and fish drying racks of Narsaq
- An overnight in UNESCO site Quebec City affords plenty of time to see Fairmont Chateau Frontenac, Notre Dame Basilica, and Terrasse Dufferin
- Appreciate the scenic cruising in impressive Prince Christian Sound, open only three months a year and 43-mile long Tasermiut Fjord
- Stroll the streets of UNESCO site Lunenburg with its unique architecture and Cap aux Meules, gateway to the Magdalen Islands
- With its reputation for great dining, Portland’s Old Port district offers a variety of warehouses converted to restaurants
- Pack light with complimentary daily laundry service
From $15,101*pp
2026 Departures: 31 Aug
2027 Departures: 27 Sep
14 NIGHTS - QUEBEC AND NEWFOUNDLAND ADVENTURE
- Montreal to Montreal -
- - Pack light with complimentary daily laundry service.
-Enjoy a stop in the small ship exclusive port of Bonne Bay, and two new to Windstar ports – St. Pierre & Miquelon and Trois-Rivières.
- Experience the best jam in Quebec City on Île d'Orléans at Confiturerie Tigidou, a well-known jam factory.
- In Baie-Comeau, meet local wildlife aboard a Zodiac, or go lobster fishing in Cap-aux-Meules, Magdalen Island.
- Discover Newfoundland's geology and wander the New World's First City when you disembark in St. John.
- Visit the Red Bay Basque Whaling Station (UNESCO site) to learn about the history of the whaling capital of the world.
- In Havre-Saint-Pierre, get up close to the largest concentration of monoliths, a natural formation made up of a single large stone or rock, in Canada.
From $9,364*pp
2026 Departures: 25 Sep
2027 Departures: 27 Sep
7 NIGHTS - BERMUDA BLISS
- Boston to San Juan -
- Spend time on self-care, whether it’s reading a book or relaxing in the complimentary thermal suite.
- Overnight in UNESCO site St. George’s with its famous pink-sand beaches and 18th century Town Hall.
- Stretch out in your spacious suite and stay in for a private happy hour.
-Dropping by the Bridge for an impromptu navigation lesson.
- Spend relaxing days at sea with time for making new friends, lounging on deck, and attending onboard enrichment programs.
- Have your camera ready for the incredible views from El Morro, San Juan’s UNESCO site.
2026 Departures: 20 Oct
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19 NIGHTS – STAR COLLECTOR: FALL LEAVES & CARIBBEAN BREEZES
– Montreal to San Juan –
- Pack light with complimentary daily laundry service.
- Begin in vibrant Montreal, known as Canada’s creative capital, with historic Old Montreal, lively cafés, and French-influenced culture.
- Enjoy an overnight in Quebec City, a UNESCO-listed gem with cobblestone streets, fortified walls, and centuries of French heritage.
- Experience the rugged beauty of Gaspé Peninsula with dramatic cliffs, sea arches, and the famous Percé Rock.
- Visit the charming fishing communities of the Magdalen Islands and Cape - Breton, including Sydney, Nova Scotia.
- Explore the maritime charm of Halifax before sailing south to the historic ports of Portland, Maine and Boston in New England.
- Cruise through the scenic Cape Cod Canal before an overnight stay in iconic New York City.
- Enjoy a two-day stay in Hamilton, Bermuda with time to explore pink-sand beaches, historic forts, and colourful colonial streets.
- Discover the historic charm of St. George’s, Bermuda before sailing south to the Caribbean
- Conclude in vibrant San Juan, where colourful colonial streets and Spanish fortresses overlook the harbour.
From $14,456*pp
2026 Departures: 9 Oct
21 NIGHTS – STAR COLLECTOR: FALL LEAVES & CARIBBEAN BREEZES
– Montreal to San Juan –
Begin in Montreal, a vibrant French-influenced city known for its historic Old Town, lively cafés, and distinctive architecture.
Enjoy an overnight stay in Quebec City, a UNESCO-listed gem with cobblestone streets, fortified walls, and centuries of French heritage.
Cruise through the dramatic landscapes of the Gaspé Peninsula, where rugged cliffs, sea arches, and colourful autumn foliage line the coast.
Visit the Magdalen Islands and Cape Breton, including Sydney and Halifax, rich in maritime culture and scenic coastal beauty.
Explore classic New England ports such as Portland and Boston before cruising through the scenic Cape Cod Canal.
Experience an overnight stay in New York City, offering time to enjoy its iconic skyline, world-class dining, and famous landmarks.
Continue south to Bermuda with extended time to discover historic forts, pink-sand beaches, and the UNESCO-listed town of St. George’s.
Sail onwards to the Caribbean, visiting idyllic islands such as St. Barts and Virgin Gorda, home to stunning beaches and the famous Baths.
Conclude your journey in San Juan, Puerto Rico, where colourful colonial streets and historic Spanish fortresses overlook the harbour
2026 Departures: 11 Oct
From $11,173*pp
From $5,164*pp