Best Windstar Cruises
Find the Best Windstar Cruises for you. Easily compare prices and find out when to book your Windstar Cruises dream vacation with our cruise search.
7 Night North America
PORTS
New York City; St Georges; St Georges; San Juan
SAIL DATE: Oct 19, 2025 - Oct 26, 2025
Interior
not available
Oceanview
$2499 $357/night
Balcony
$3499 $499/night
Suite
$5499 $785/night
14 Night Canada - New England
PORTS
Reykjavik, Iceland; Prince Christian Sound East; Qaqortoq, Greenland; Narsaq; Nanortalik, Gree... Boston
SAIL DATE: Aug 31, 2026 - Sep 14, 2026
Interior
not available
Oceanview
$5899 $421/night
Balcony
$8319 $594/night
Suite
$11899 $849/night
25 Night Canada - New England
PORTS
Boston; Rockland, Maine; Portland; Halifax; Sydney; Cap Aux Meules; Gaspe, Quebec; Quebec Ci... Montreal
SAIL DATE: Sep 14, 2026 - Oct 09, 2026
Interior
not available
Oceanview
$10999 $439/night
Balcony
$15499 $619/night
Suite
$25779 $1031/night
25 Night Canada - New England
PORTS
Montreal; Quebec City, Quebec; Baie-Comeau, Quebec; Cap Aux Meules; St Pierre & Miquelon;... Boston
SAIL DATE: Sep 25, 2026 - Oct 20, 2026
Interior
not available
Oceanview
$10999 $439/night
Balcony
$15499 $619/night
Suite
$25779 $1031/night
14 Night Canada - New England
PORTS
Montreal; Quebec City, Quebec; Baie-Comeau, Quebec; Cap Aux Meules; St. Pierre & Miquel... Montreal
SAIL DATE: Sep 25, 2026 - Oct 09, 2026
Interior
not available
Oceanview
$7199 $514/night
Balcony
$9619 $687/night
Suite
$15039 $1074/night
14 Night Canada - New England
PORTS
Reykjavik, Iceland; Prince Christian Sound East; Qaqortoq, Greenland; Narsaq; Nanortalik, Gr... Montreal
SAIL DATE: Sep 01, 2025 - Sep 15, 2025
Interior
not available
Oceanview
$5718 $408/night
Balcony
$8919 $637/night
Suite
$11579 $827/night
11 Night Canada - New England
PORTS
Boston; Rockland, Maine; Portland; Halifax; Sydney; Cap Aux Meules; Gaspe, Quebec; Quebec Ci... Montreal
SAIL DATE: Sep 14, 2026 - Sep 25, 2026
Interior
not available
Oceanview
$5899 $536/night
Balcony
$8079 $734/night
Suite
$9969 $906/night
11 Night Canada - New England
PORTS
Montreal; Quebec City, Quebec; Quebec City, Quebec; Gaspe, Quebec; Cap Aux Meules; Sydney; Hal... Boston
SAIL DATE: Oct 09, 2026 - Oct 20, 2026
Interior
not available
Oceanview
$5899 $536/night
Balcony
$8079 $734/night
Suite
$9969 $906/night
11 Night Canada - New England
PORTS
Boston; Portland; Lunenburg, Nova Scotia; Halifax; Sydney; Cap Aux Meules; Gaspe, Quebec; Qu... Montreal
SAIL DATE: Sep 26, 2025 - Oct 07, 2025
Interior
not available
Oceanview
$5999 $545/night
Balcony
$8179 $743/night
Suite
$5999 $545/night
11 Night Canada - New England
PORTS
Montreal; Quebec City, Quebec; Quebec City, Quebec; Gaspe, Quebec; Cap Aux Meules; Sydney; Hal... Boston
SAIL DATE: Sep 15, 2025 - Sep 26, 2025
Interior
not available
Oceanview
$6199 $563/night
Balcony
not available
Suite
not available
The best Windstar cruises combine excellent service, onboard amenities, and an exciting itinerary - and you can find the perfect sailing for you with cruisewatch.com. Plus, our innovative price prediction (which you won’t find anywhere else) combined with free automatic price alerts ensure we can offer our customers up to 70% off on Windstar cruises. Don’t miss out on this free service and wind up paying too much for your dream vacation on Windstar Cruises. Let us do the heavy lifting so you can focus on what matters most: making the most out of your unforgettable Windstar Cruises cruise!