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 Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Soper's... Philipsburg, Saint-Martin
SAIL DATE: Jan 31, 2026 - Feb 07, 2026
Interior
not available
Oceanview
$1484 $212/night
Balcony
not available
Suite
$6199 $885/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla; Soper's Hole,... Bridgetown
SAIL DATE: Jan 04, 2026 - Jan 18, 2026
Interior
not available
Oceanview
$4899 $349/night
Balcony
not available
Suite
$6299 $449/night
8 Night Panama Canal
PORTS
Puerto Caldera, Costa Rica; Punta Leona; Puerto Quepos, Costa Rica; Puerto Jimenez (Gol... Balboa/Panama
SAIL DATE: Jan 03, 2026 - Jan 11, 2026
Interior
not available
Oceanview
$2699 $337/night
Balcony
$3959 $494/night
Suite
$5199 $649/night
8 Night Panama Canal
PORTS
Balboa - Fuerte Amador; Isla Parida, Panama; Puerto Jimenez (Golfo Dulce),... Puerto Caldera, Costa Rica
SAIL DATE: Jan 25, 2026 - Feb 02, 2026
Interior
not available
Oceanview
$2699 $337/night
Balcony
$3959 $494/night
Suite
$5199 $649/night
55 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Jan 04, 2026 - Feb 28, 2026
Interior
not available
Oceanview
$19599 $356/night
Balcony
not available
Suite
$24499 $445/night
15 Night Caribbean
PORTS
Bridgetown; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Soufriere, St. Luc... Colon, Panama
SAIL DATE: Jan 25, 2026 - Feb 09, 2026
Interior
not available
Oceanview
$5399 $359/night
Balcony
not available
Suite
$6799 $453/night
10 Night Caribbean
PORTS
Bridgetown; Mayreau, Grenadines; Roseau; Anse Mitan; Deshaies, Guadeloupe;... Philipsburg, Saint-Martin
SAIL DATE: Jan 04, 2026 - Jan 14, 2026
Interior
not available
Oceanview
$3599 $359/night
Balcony
not available
Suite
not available
8 Night Panama Canal
PORTS
Oranjestad; Cartagena, Spain; Cartagena, Spain; Bocas Del Toro, Panama; San Bl... Balboa - Fuerte Amador
SAIL DATE: Jan 17, 2026 - Jan 25, 2026
Interior
not available
Oceanview
$3099 $387/night
Balcony
$4359 $544/night
Suite
$5599 $699/night
7 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Jan 04, 2026 - Jan 11, 2026
Interior
not available
Oceanview
$3099 $442/night
Balcony
not available
Suite
$3799 $542/night
7 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Basseterre; Gustavia; St. John's, Antigua; Iles Des Saintes (We... Bridgetown
SAIL DATE: Jan 11, 2026 - Jan 18, 2026
Interior
not available
Oceanview
$2999 $428/night
Balcony
not available
Suite
$3899 $557/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!