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.
6 Night Panama Canal
PORTS
Balboa/Panama; Bocas Del Toro, Panama; San Blas Islands, Panama; Cartagena, Spain; Oranjestad
SAIL DATE: Jan 11, 2026 - Jan 17, 2026
Interior
not available
Oceanview
$1404 $234/night
Balcony
$2160 $360/night
Suite
$4904 $817/night
3 Night Western Mediterranean
PORTS
Civitavecchia; Portovenere, Italy; Bonifacio, Corsica; Civitavecchia
SAIL DATE: May 31, 2026 - Jun 03, 2026
Interior
not available
Oceanview
$1111 $370/night
Balcony
not available
Suite
$1331 $443/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Soper's... Philipsburg, Saint-Martin
SAIL DATE: Mar 28, 2026 - Apr 03, 2026
Interior
not available
Oceanview
$2399 $399/night
Balcony
not available
Suite
$3299 $549/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Dec 14, 2025 - Dec 20, 2025
Interior
not available
Oceanview
$2599 $433/night
Balcony
not available
Suite
$3299 $549/night
6 Night Caribbean
PORTS
San Juan; Santo Domingo, Dominican Republic; Cartagena, Spain; Cartagena, Spain; San Bl... Colon, Panama
SAIL DATE: Dec 07, 2025 - Dec 13, 2025
Interior
not available
Oceanview
$2599 $433/night
Balcony
$3859 $643/night
Suite
$5099 $849/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Soper's... Philipsburg, Saint-Martin
SAIL DATE: Jan 31, 2026 - Feb 06, 2026
Interior
not available
Oceanview
$2499 $416/night
Balcony
not available
Suite
$5999 $999/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Mar 07, 2026 - Mar 13, 2026
Interior
not available
Oceanview
$2699 $449/night
Balcony
not available
Suite
$3599 $599/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Prickly... Philipsburg, Saint-Martin
SAIL DATE: Feb 21, 2026 - Feb 27, 2026
Interior
not available
Oceanview
$2599 $433/night
Balcony
not available
Suite
$6099 $1016/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Mar 14, 2026 - Mar 20, 2026
Interior
not available
Oceanview
$2799 $466/night
Balcony
not available
Suite
$3699 $616/night
6 Night Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Prickly... Philipsburg, Saint-Martin
SAIL DATE: Jan 24, 2026 - Jan 30, 2026
Interior
not available
Oceanview
$2699 $449/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!