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.
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Iles Des Saintes (West Indies); May... Philipsburg, Saint-Martin
SAIL DATE: Jan 09, 2027 - Jan 23, 2027
Interior
not available
Oceanview
$3999 $285/night
Balcony
not available
Suite
$5699 $407/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Jan 02, 2027 - Jan 16, 2027
Interior
not available
Oceanview
$3999 $285/night
Balcony
not available
Suite
$5699 $407/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Road Bay, Anguilla; Soper's Hole, Tortola, B.V.I... Philipsburg, Saint-Martin
SAIL DATE: Jan 16, 2027 - Jan 30, 2027
Interior
not available
Oceanview
$3999 $285/night
Balcony
not available
Suite
$5699 $407/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Road Bay, Anguilla; Soper's Hole, Tortola, B.V.I... Philipsburg, Saint-Martin
SAIL DATE: Jan 30, 2027 - Feb 13, 2027
Interior
not available
Oceanview
$4099 $292/night
Balcony
not available
Suite
$5799 $414/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Roseau; Mayreau, Grenadines; Iles D... Philipsburg, Saint-Martin
SAIL DATE: Jan 23, 2027 - Feb 06, 2027
Interior
not available
Oceanview
$4099 $292/night
Balcony
not available
Suite
$5799 $414/night
14 Night N-A
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Jan 03, 2027 - Jan 17, 2027
Interior
not available
Oceanview
$4299 $307/night
Balcony
$6719 $479/night
Suite
$9199 $657/night
10 Night Canary Islands
PORTS
Santa Cruz De Tenerife, Canary Islands; Lanzarote; Funchal, Ma... Santa Cruz De Tenerife, Canary Islands
SAIL DATE: Jan 06, 2027 - Jan 16, 2027
Interior
not available
Oceanview
$3499 $349/night
Balcony
not available
Suite
not available
10 Night Canary Islands
PORTS
Santa Cruz De Tenerife, Canary Islands; Lanzarote; Funchal, Ma... Santa Cruz De Tenerife, Canary Islands
SAIL DATE: Jan 16, 2027 - Jan 26, 2027
Interior
not available
Oceanview
$3499 $349/night
Balcony
not available
Suite
not available
10 Night Western Mediterranean
PORTS
Santa Cruz De Tenerife, Canary Islands; Las Palmas; Las Palmas; San Sebastian De La Gomera,... Seville
SAIL DATE: Jan 26, 2027 - Feb 05, 2027
Interior
not available
Oceanview
$3499 $349/night
Balcony
not available
Suite
$6499 $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!