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.
15 Night Transatlantic
PORTS
Bridgetown; Lisbon
SAIL DATE: Mar 28, 2026 - Apr 12, 2026
Interior
not available
Oceanview
$1594 $106/night
Balcony
not available
Suite
$5499 $366/night
7 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Oct 26, 2025 - Nov 02, 2025
Interior
not available
Oceanview
$2505 $357/night
Balcony
$3765 $537/night
Suite
$5005 $715/night
14 Night Transatlantic
PORTS
Philipsburg, Saint-Martin; Ponta Delgada, Azores; Lisbon
SAIL DATE: Apr 04, 2026 - Apr 18, 2026
Interior
not available
Oceanview
$2599 $185/night
Balcony
not available
Suite
$3199 $228/night
11 Night Western Mediterranean
PORTS
Bordeaux, France; Bordeaux, France; Bilbao, Spain; Bilbao, Spain; Ferrol, Spain; Vigo; Cadi... Barcelona
SAIL DATE: Aug 24, 2025 - Sep 04, 2025
Interior
not available
Oceanview
$2959 $269/night
Balcony
$4703 $427/night
Suite
$7769 $706/night
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
16 Night Transatlantic
PORTS
Bridgetown; Lisbon; Amsterdam
SAIL DATE: Mar 22, 2026 - Apr 07, 2026
Interior
not available
Oceanview
$3099 $193/night
Balcony
$3899 $243/night
Suite
$5199 $324/night
7 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Roseau; Mayreau, Grenadines; Iles D... Philipsburg, Saint-Martin
SAIL DATE: Dec 07, 2025 - Dec 14, 2025
Interior
not available
Oceanview
$1221 $174/night
Balcony
not available
Suite
$1716 $245/night
7 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Dec 14, 2025 - Dec 21, 2025
Interior
not available
Oceanview
$1374 $196/night
Balcony
not available
Suite
$1869 $267/night
7 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Roseau; Mayreau, Grenadines; Iles D... Philipsburg, Saint-Martin
SAIL DATE: Mar 21, 2026 - Mar 28, 2026
Interior
not available
Oceanview
$2599 $371/night
Balcony
not available
Suite
$3499 $499/night
14 Night Transatlantic
PORTS
Lisbon; St. John's, Antigua; Philipsburg, Saint-Martin
SAIL DATE: Nov 18, 2025 - Dec 02, 2025
Interior
not available
Oceanview
$2899 $207/night
Balcony
not available
Suite
$3499 $249/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!