Southeast Canadian Explorations
 
Boston to Montreal
Mon Sep 14, 2026 - Fri Sep 25, 2026,
 11 days
 on Star Pride
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Starting from $5,299 USD
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Boston to Montreal
Quebec’s French-flavored history, the fusion of Acadian and Scottish cultures in Nova Scotia—each province distills its own blend of Old World and New, bucolic and urbane. Overnight in Quebec City and browse the shops and boulangeries along picturesque Petit Champlain, the oldest street in North America. Fall under the spell of UNESCO site Lunenburg’s charming waterfront, and Halifax with its lively pub culture and majestic Citadel. Take in the brilliance of New England’s fall colors and the historic sites of Boston, one of America’s oldest cities.
 
voyage map
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Day 1: Boston
Founded in 1630 by Puritan settlers, Boston is one of the oldest cities in the U.S. It was a pivotal place during the American Revolution for the Boston Massacre, the Boston Tea Party, the Battle of Bunker Hill and the Siege of Boston. Tourists to Boston see the Faneuil Hall Marketplace, the JFK Library and Museum, the Museum of Fine Arts, the New England Aquarium, and the USS Constitution.
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Day 2: Rockland
Rockland is a classic Maine coastal town and the lobster capital of the world. It has been recognized by National Geographic Travel as the “Top Adventure Town in Maine,” and “Coolest Small Town in US” by Budget Travel. Downtown Rockland is full of historic homes, shops and restaurants serving fresh local seafood. An impressive collection of Maine art can be found at the Farnsworth Art Museum and Wyeth Center. Bordering Penobscot Bay, Rockland is also known internationally as one of the best recreational sailing areas of the world.
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Day 3: Portland
The New England charm of Portland is a delightful mix of stylish and sophisticated, modest and folksy, with a reputation for great dining. There is a plethora of local art and music, lovely parks and a pleasing array of 19th century architecture including beautiful Victorian-era homes. The cobblestone lanes of the Old Port district waterfront are alive with working fishing piers and warehouses converted into shops and restaurants.
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Day 5: Halifax
The capital of Nova Scotia was ranked the 4th best place to live in Canada back in 2012. It is a city with more pubs and clubs per capita than any other Canadian city and even one of the mayors was a brewmaster. The boardwalk on the waterfront follows the water’s edge and is lined with unique shops. Halifax is home to the longest running saltwater ferry and a 200-year-old restored fishing village. Be sure to find time to try fabled donair (pita, meat and sauce), the official food of Halifax.
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Day 6: Sydney, Nova Scotia, Canada
Sydney is the largest city on Cape Breton Island where the hub of activity can be found at the waterfront where you’ll find the world’s largest fiddle. A popular tourist destination, grab a Cape Breton Artisan Trail Map and immerse yourself in the lives of local artisans. Hit Casino Nova Scotia or take a mining tour with the help of a local miner. Check out the year-round indoor Cape Breton Farmers’ Market or discover the history of the Membertou people at their Heritage Park.
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Day 7: Cap aux Meules
With its village main street and many restaurants and bars, charming Cap aux Meules is the gateway to the Magdalen Islands Archipelago located in the middle of the Gulf of St. Lawrence. The port bustles with fishing boats, ferries, and a well-equipped marina offering a huge travel lift crane for dry dock. Sites to see include the church of St. Pierre, constructed from the wreckage of ships and the lighthouse which now warns of the offshore shoals.
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Day 8: Gaspe
Four hundred miles northeast of Quebec City lies Gaspe, one of National Geographic’s Canada’s 50 Places of a Lifetime. This wonderful wilderness area is home to four national parks; Perce Rock; North America’s largest gannet colony; lighthouses and remarkable historic sites. Visit the modern cathedral built almost entirely of wood and make sure to try some of the local specialties such as French-styled lobsters and game.
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Day 10: Quebec City
A focal point of French culture and one of North America’s oldest and most beautiful cities, Quebec City sits above the St. Lawrence River on a rocky spur with 328-foot cliffs. This French-speaking city was established in 1608 with the only fortified city walls remaining in America north of Mexico, and declared a UNESCO World Heritage City. The Old Town is packed with museums, cobblestone streets and mansard-roofed houses begging to be explored. Other historic attractions include the Fairmont Chateau Frontenac, Notre Dame Basilica, Battlefields Park and Terrasse Dufferin.
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Day 11: Quebec City
A focal point of French culture and one of North America’s oldest and most beautiful cities, Quebec City sits above the St. Lawrence River on a rocky spur with 328-foot cliffs. This French-speaking city was established in 1608 with the only fortified city walls remaining in America north of Mexico, and declared a UNESCO World Heritage City. The Old Town is packed with museums, cobblestone streets and mansard-roofed houses begging to be explored. Other historic attractions include the Fairmont Chateau Frontenac, Notre Dame Basilica, Battlefields Park and Terrasse Dufferin.
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Day 12: Montreal
Montreal is full of interesting architecture and is considered by many to be the creative capital of Canada. Named a UNESCO City of Design, Montreal attractions include Basilique Notre-Dame, Stade Olympique, Canal de Lachine, Old Montreal, and Habitat 67. Enjoy a meal at one of the terraced cafes of Plateau Mont-Royal and make sure you try Kamouraska lamb, Arctic char and poutine.
Popular Highlights
Boston
Plan extra time in historic Boston, one of America's oldest cities and home of the JFK Library.
Gaspe
See the majesty of Perce Rock near Gaspe
East Coast
Witness the vibrant beauty of the fall foliage along the East Coast of the United States & Canada.
Halifax
Learn the role vibrant Halifax played when the Titanic sank.
Montreal
Try the unique cuisine of Montreal - poutine, Arctic char and Kamouraska lamb.
Portland
Enjoy the New England charm and lovely Victorian-era architecture in Portland.
Quebec City
Catch the attractions of Quebec City, a UNESCO site when you overnight there
Itinerary at a Glance
Date
Port
Arrive
Depart
Watersports
PlatformWatersports Platform: 
Mon Sep 14
Boston
Arrive:  
Depart:  5:00 PM
Watersports Platform: 
Tue Sep 15
Rockland
Arrive:  8:00 AM
Depart:  6:00 PM
Watersports Platform: 
Wed Sep 16
Portland
Arrive:  8:00 AM
Depart:  11:00 PM
Watersports Platform: 
Thu Sep 17
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Fri Sep 18
Halifax
Arrive:  8:00 AM
Depart:  4:00 PM
Watersports Platform: 
Sat Sep 19
Sydney, Nova Scotia, Canada
Arrive:  1:00 PM
Depart:  7:00 PM
Watersports Platform: 
Sun Sep 20
Cap aux Meules
Arrive:  10:00 AM
Depart:  6:00 PM
Watersports Platform: 
Mon Sep 21
Gaspe
Arrive:  1:00 PM
Depart:  7:00 PM
Watersports Platform: 
Tue Sep 22
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Wed Sep 23
Quebec City
Arrive:  9:00 AM
Depart:  
Watersports Platform: 
Thu Sep 24
Quebec City
Arrive:  
Depart:  4:00 PM
Watersports Platform: 
Fri Sep 25
Montreal
Arrive:  8:00 AM
Depart:  
Watersports Platform: 
“There was just so much to see! Colorful little fishing harbors and lighthouses one day, old weatherworn stone forts the next, and scenes that were just awe-inspiring nature, like the light shining through the arch of Percé rock or the view from the top of Cadillac Mountain.”
The Story
Fresh water flows east from the Great Lakes, the Canadian Shield, and the St. Lawrence River, arriving at the shallow Gulf of St. Lawrence where it meets the salt water confluence of the cold Labrador current and the Gulf Stream. The conditions are perfect for an explosion of marine life, which in turn attracts indigenous communities and later, European settlers. This was the New World, and the Old World wanted it badly, drawn by resources the likes of which they’d never seen.

This area is still a prize, rich with architectural wonders, cultures, and spectacular scenery. In the course of a day, you might pass an 18th-century garrison, iconic lighthouses, and restored red brick warehouses brimming with galleries, microbreweries, and hip farmers’ markets. Watercolor fishing villages come to life under the squawk of seagulls. French conversations flow with the scent of fresh croissants from boulangeries. And colonial history is literally under your feet.
Insider Tips:
  • The Old Town part of Quebec is intoxicating in daylight, but in the evening it takes on a particular magic. With an overnight stay in Quebec City you can walk through this sleepy European village after other tourists have retired.
  • Few people know that Nova Scotia is one of the smallest, oldest, wine-growing regions in North America. Vines were planted here as early as the 17th century, and the climate is ideal for whites and acid-bright sparkling wines. Try some if you get the chance.
  • Bird watchers make a note when you’re in Gaspé. If you take the cruise around Bonaventure Island, you will probably spot northern gannets (the park is home to the world’s largest colony) as well as other seabirds, including Atlantic puffins.
  • Halifax is home to the Canadian version of Ellis Island, and you’ll find it at Pier 21. Nearly a million immigrants entered here at what is now the Canadian Museum of Immigration. Just a short walk away is the Halifax Farmers' Market, the oldest continuously running market in North America (dating to 1750).
  • As you walk around the UNESCO town of Lunenburg, “the best surviving example of a planned British colonial settlement in North America,” watch for the Lunenburg Bump on the colorful Victorian homes. The extended middle dormer is a trademark of the town, whose homes were crafted by shipwrights during their off season.
Accommodations & Pricing
Star Porthole Suite
Star Porthole Suite
These rooms represent a nod to the sailing tradition of porthole windows. And while sailors might have had cramped quarters, your 277 square foot stateroom is wonderfully spacious and furnished with all the modern amenities and comforts of home.
? Cruise only from $5,299 per guest
? All-inclusive price from $5,299 per guest
Ocean View Suite
Ocean View Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, and savor a treat from the fresh fruit bowl.
? Cruise only from $5,739 per guest
? All-inclusive price from $5,739 per guest
Ocean View Suite 1
Ocean View Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $5,899 per guest
? All-inclusive price from $5,899 per guest
Star Ocean View Suite 1
Star Ocean View Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $5,999 per guest
? All-inclusive price from $5,999 per guest
Ocean View Suite 2
Ocean View Suite 2
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $6,069 per guest
? All-inclusive price from $6,069 per guest
Ocean View Suite 3
Ocean View Suite 3
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $6,179 per guest
? All-inclusive price from $6,179 per guest
Balcony Suite
Balcony Suite
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $7,479 per guest
? All-inclusive price from $7,479 per guest
Star Balcony Suite
Star Balcony Suite
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $7,709 per guest
? All-inclusive price from $7,709 per guest
Balcony Suite 1
Balcony Suite 1
Stylish comfort and ocean views welcome you in 277 square feet. Your queen bed (which can be separated as twins if you prefer) features luxurious Egyptian cotton linens. Enjoy a luxurious soak in your full-size tub or an invigorating shower, then wrap up in your waffle-weave robe and slippers, savor a treat from the fresh fruit bowl, or simply stretch out and enjoy the fresh flowers.
? Cruise only from $7,939 per guest
? All-inclusive price from $7,939 per guest
Star Balcony Suite 1
Star Balcony Suite 1
As soon as you walk through the door, you’re greeted with an open living area for a more welcoming entrance. Drift off to sleep by the window in your queen bed as you watch the same stars that sailors used to navigate the seas hundreds of years ago.
? Cruise only from $8,269 per guest
? All-inclusive price from $8,269 per guest
Deluxe Suite
Deluxe Suite
Brand new Deluxe Suites welcome you with 468 square feet of casually elegant living space and an ocean viewing French balcony. All these suites feature 3rd berths, and a sleep-inducing queen bed easily converted to twins.
? Cruise only from $9,369 per guest
? All-inclusive price from $9,369 per guest
Classic Suite
Classic Suite
Relax in 400 to 530 spacious square feet. Your living area offers beautiful views from the forward-facing window and French doors onto your private veranda. Two spacious closets give you plenty of room to unpack.
? Cruise only from $10,689 per guest
? All-inclusive price from $10,689 per guest
Owner's Suite
Owner's Suite
With 575 square feet, your Owner’s Suite offers separate living room and dining areas. A veranda, Interactive TVs and a full master bath and separate powder room indulge you in spacious comfort. 
? Cruise only from $12,339 per guest
? All-inclusive price from $12,339 per guest
The Windstar Life
The Windstar staff-to-guest ratio is 1:1.5, and it shows.The moment you board you’ll feel it: an ever-attentive crew at your service, providing you with what you want and need, when you want and need it.
Friendly and Relaxed Atmosphere
Signature Onboard Barbecue
Cooking Demonstrations
Genuine and Thoughtful Crew
Crew Talent Show
Open Bridge
Local and Live Performances
Relax at the Pool or Hot Tub
Complimentary 24 Hour Room Service
Signature Sail Away
Shopping With The Chef
Take In The Sun
Watersports Platform
Enjoy regionally inspired treatments at World Spa by Windstar
Relax With A Morning Yoga Session
ALL DATES &
FARES
Early Booking Offer 2026 & 2027
Pick Your Perk
Great cruise-only fares or make it an all-inclusive voyage with Wi-Fi, unlimited beer, wine, and cocktails, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Mon, Sep 15 - Fri, Sep 26, 2025
STAR PRIDE
$7,188
$6,099
Fri, Sep 26 - Tue, Oct 7, 2025
STAR PRIDE
$6,988
$5,899
Mon, Sep 14 - Fri, Sep 25, 2026
STAR PRIDE
$5,299
$5,299
THIS
SAILING
Fri, Oct 9 - Tue, Oct 20, 2026
STAR PRIDE
$5,299
$5,299