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.
13 Night Caribbean
PORTS
San Juan; Santo Domingo, Dominican Republic; Cartagena, Spain; Cartagena,... Puerto Caldera, Costa Rica
SAIL DATE: Dec 07, 2025 - Dec 20, 2025
Interior
not available
Oceanview
$2308 $177/night
Balcony
$3637 $279/night
Suite
$9099 $699/night
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
$3899 $278/night
Balcony
not available
Suite
$5599 $399/night
10 Night Western Mediterranean
PORTS
Santa Cruz De Tenerife, Canary Islands; San Sebastian De La Go... Santa Cruz De Tenerife, Canary Islands
SAIL DATE: Dec 20, 2025 - Dec 30, 2025
Interior
not available
Oceanview
$2589 $258/night
Balcony
not available
Suite
$8699 $869/night
12 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Soper's Hole, Tortola, B.V.I.; Jost Van Dyke; Jo... Philipsburg, Saint-Martin
SAIL DATE: Dec 02, 2025 - Dec 14, 2025
Interior
not available
Oceanview
$3899 $324/night
Balcony
not available
Suite
$5499 $458/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Dec 14, 2025 - Dec 28, 2025
Interior
not available
Oceanview
$4599 $328/night
Balcony
not available
Suite
$6299 $449/night
14 Night Southern Europe
PORTS
Malaga; Malaga; Gibraltar (U.K.); Cartagena, Spain; Valencia, Spain; Palma de Mallorca... Civitavecchia
SAIL DATE: Dec 13, 2025 - Dec 27, 2025
Interior
not available
Oceanview
$4899 $349/night
Balcony
$7679 $548/night
Suite
$10719 $765/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Charlestown; Roseau; Mayreau, Grenadines; Iles D... Philipsburg, Saint-Martin
SAIL DATE: Dec 21, 2025 - Jan 04, 2026
Interior
not available
Oceanview
$5199 $371/night
Balcony
not available
Suite
$6899 $492/night
11 Night South Pacific
PORTS
Papeete, Tahiti; Fakarava, Tuamotu Archipelago; Rangiroa, French Polynesia; Motu Maha... Papeete, Tahiti
SAIL DATE: Dec 18, 2025 - Dec 29, 2025
Interior
not available
Oceanview
$4599 $418/night
Balcony
$7019 $638/night
Suite
$9659 $878/night
11 Night Panama Canal
PORTS
Colon, Panama; Manta, Ecuador; Manta, Ecuador; Guayaquil, Equador; Guayaquil, Equa... Trujillo, Honduras
SAIL DATE: Dec 27, 2025 - Jan 07, 2026
Interior
not available
Oceanview
$4999 $454/night
Balcony
$6469 $588/night
Suite
$7699 $699/night
10 Night Western Mediterranean
PORTS
Santa Cruz De Tenerife, Canary Islands; Santa Cruz De Tenerife... Santa Cruz De Tenerife, Canary Islands
SAIL DATE: Dec 30, 2025 - Jan 09, 2026
Interior
not available
Oceanview
$3899 $389/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!