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.
21 Night Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Soper's Hole, Tortola, B.V... Lisbon
SAIL DATE: Mar 28, 2026 - Apr 18, 2026
Interior
not available
Oceanview
$4099 $195/night
Balcony
not available
Suite
$5499 $261/night
7 Night Caribbean
PORTS
Oranjestad; Kralendijk; Pigeon Island, St. Lucia; The Pitons; Port Elizabeth, Bequia, Gren... Bridgetown
SAIL DATE: Mar 15, 2026 - Mar 22, 2026
Interior
not available
Oceanview
$1483 $211/night
Balcony
$2176 $310/night
Suite
$5199 $742/night
7 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 16, 2025 - Nov 23, 2025
Interior
not available
Oceanview
$1483 $211/night
Balcony
$2176 $310/night
Suite
$5199 $742/night
6 Night Caribbean
PORTS
Colon, Panama; Bocas Del Toro, Panama; San Blas Islands, Panama; Cartagena, Spain; Cartage... Oranjestad
SAIL DATE: Mar 09, 2026 - Mar 15, 2026
Interior
not available
Oceanview
$1374 $229/night
Balcony
$2067 $344/night
Suite
$4999 $833/night
14 Night Caribbean Eastern
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 16, 2025 - Nov 30, 2025
Interior
not available
Oceanview
$3739 $267/night
Balcony
$5621 $401/night
Suite
$9099 $649/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Roseau; Mayreau, Grenadines; Iles D... Philipsburg, Saint-Martin
SAIL DATE: Mar 21, 2026 - Apr 04, 2026
Interior
not available
Oceanview
$4099 $292/night
Balcony
not available
Suite
$5799 $414/night
25 Night Caribbean
PORTS
Lisbon; Bridgetown; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; St. George... Colon, Panama
SAIL DATE: Nov 04, 2025 - Nov 29, 2025
Interior
not available
Oceanview
$6399 $255/night
Balcony
not available
Suite
not available
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Roseau; Mayreau, Grenadines; Iles D... Philipsburg, Saint-Martin
SAIL DATE: Dec 07, 2025 - Dec 21, 2025
Interior
not available
Oceanview
$4199 $299/night
Balcony
not available
Suite
$5599 $399/night
20 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Mar... Puerto Caldera, Costa Rica
SAIL DATE: Nov 30, 2025 - Dec 20, 2025
Interior
not available
Oceanview
$5999 $299/night
Balcony
$9674 $483/night
Suite
$13399 $669/night
14 Night Caribbean Eastern
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Nov 09, 2025 - Nov 23, 2025
Interior
not available
Oceanview
$4199 $299/night
Balcony
$6614 $472/night
Suite
$9099 $649/night
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!