Small Ship CANADA & NEW ENGLAND CRUISES

 
Canada & New England in Windstar Style

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.

WINDSTAR VOYAGES TO CANADA & NEW ENGLAND
SPECIAL AVAILABLE Mind, Body and Spirit Collection: Bermuda Bliss

Mind, Body and Spirit Collection: Bermuda Bliss

Port to port
New York City to San Juan
Duration
7 Days
All-Inclusive From?
$2,499
Cruise Only From?
$2,499

Bermuda Bliss

Port to port
Boston to San Juan
Duration
8 Days
All-Inclusive From?
$3,191
Cruise Only From?
$2,399
SPECIAL AVAILABLE Greenland: North Atlantic Odyssey

Greenland: North Atlantic Odyssey

Port to port
Reykjavik to Boston
Duration
14 Days
All-Inclusive From?
$5,899
Cruise Only From?
$5,899
SPECIAL AVAILABLE James Beard Foundation & Wine Cruise: Southeast Canadian Explorations

James Beard Foundation & Wine Cruise: Southeast Canadian Explorations

Port to port
Montreal to New York City
Duration
12 Days
All-Inclusive From?
$7,599
Cruise Only From?
$7,599

Quebec and Newfoundland Adventure

Port to port
Montreal to Montreal
Duration
14 Days
All-Inclusive From?
$8,585
Cruise Only From?
$7,199
SPECIAL AVAILABLE Southeast Canadian Explorations

Southeast Canadian Explorations

Port to port
Boston to Montreal
Duration
11 Days
All-Inclusive From?
$6,988
Cruise Only From?
$5,899

Star Collector: Autumn in Newfoundland and New England

Port to port
Boston to Montreal
Duration
25 Days
All-Inclusive From?
$13,474
Cruise Only From?
$10,999
SPECIAL AVAILABLE Star Collector: Fall Leaves & Caribbean Breezes

Star Collector: Fall Leaves & Caribbean Breezes

Port to port
Montreal to San Juan
Duration
19 Days
All-Inclusive From?
$7,980
Cruise Only From?
$6,099
SPECIAL AVAILABLE Star Collector: Greenland Fjords, Canadian Maritimes

Star Collector: Greenland Fjords, Canadian Maritimes

Port to port
Reykjavik to Boston
Duration
25 Days
All-Inclusive From?
$9,399
Cruise Only From?
$9,399
SPECIAL AVAILABLE Star Collector: North Atlantic Explorer

Star Collector: North Atlantic Explorer

Port to port
Reykjavik to Montreal
Duration
21 Days
All-Inclusive From?
$21,719
Cruise Only From?
$21,719
Star Collector: Autumn in Newfoundland and New England
Port to port
Montreal to Boston
Duration
25 days
Day
Port
Day 1
Montreal
Day 2
Quebec City
Day 3
Baie-Comeau, Quebec, Canada
Day 4
AT SEA
Day 5
Cap aux Meules
Day 6
St. Pierre & Miquelon
Day 7
St. John’s
Day 8
St. John’s
Day 9
St. Anthony
Day 10
Red Bay
Day 11
Bonne Bay / Woody Point
Day 12
Havre St. Pierre
Day 13
AT SEA
Day 14
Trois-Rivières, Canada
Day 15
Montreal
Day 16
Quebec City
Day 17
Quebec City
Day 18
AT SEA
Day 19
Gaspe
Day 20
Cap aux Meules
Day 21
Sydney, Nova Scotia, Canada
Day 22
Halifax
Day 23
AT SEA
Day 24
Portland
Day 25
Rockland
Day 26
Boston
ALL DATES &
FARES
Great cruise-only fares or make it an all-inclusive voyage with unlimited select beer, wine, and cocktails, Wi-Fi, and gratuities. From $99 per guest per day.
Date
Ship
All-Inclusive
From
Cruise Only
From
Mon
Sep 14
2026
STAR PRIDE
$13,474
$10,999
Fri
Sep 25
2026
STAR PRIDE
$13,474
$10,999
Click on the date to view the map and itinerary by date