Southeast Canadian Explorations
 
Montreal to Boston
Fri Oct 9, 2026 - Tue Oct 20, 2026,
 11 days
 on Star Pride
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Starting from $5,299 USD
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Montreal to Boston
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
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.
Itinerary at a Glance
Date
Port
Arrive
Depart
MarinaWatersports Platform: 
Fri Oct 9
Montreal
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Sat Oct 10
Quebec City
Arrive:  9:00 AM
Depart:  
Watersports Platform: 
Sun Oct 11
Quebec City
Arrive:  
Depart:  6:00 PM
Watersports Platform: 
Mon Oct 12
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Tue Oct 13
Gaspe
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Wed Oct 14
Cap aux Meules
Arrive:  11:00 AM
Depart:  6:00 PM
Watersports Platform: 
Thu Oct 15
Sydney, Nova Scotia, Canada
Arrive:  7:00 AM
Depart:  2:00 PM
Watersports Platform: 
Fri Oct 16
Halifax
Arrive:  11:00 AM
Depart:  11:00 PM
Watersports Platform: 
Sat Oct 17
AT SEA
Arrive:  
Depart:  
Watersports Platform: 
Sun Oct 18
Portland
Arrive:  8:00 AM
Depart:  10:00 PM
Watersports Platform: 
Mon Oct 19
Rockland
Arrive:  8:00 AM
Depart:  5:00 PM
Watersports Platform: 
Tue Oct 20
Boston
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
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
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 select 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
Fri, Oct 9 - Tue, Oct 20, 2026
STAR PRIDE
$5,299
$5,299
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