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
$1765 $117/night
Balcony
not available
Suite
$5525 $368/night
20 Night Caribbean
PORTS
Lisbon; Funchal, Madeira; Bridgetown; Anse Mitan; Pigeon Island, St. Lucia; Pigeon Island,... Bridgetown
SAIL DATE: Nov 14, 2026 - Dec 04, 2026
Interior
not available
Oceanview
$4199 $209/night
Balcony
$6199 $309/night
Suite
$8799 $439/night
16 Night N-A
PORTS
Oranjestad; Cartagena, Spain; Cartagena, Spain; Bocas Del Toro, Panama; Sa... Puerto Caldera, Costa Rica
SAIL DATE: Dec 12, 2026 - Dec 28, 2026
Interior
not available
Oceanview
$3999 $249/night
Balcony
$6419 $401/night
Suite
$8899 $556/night
16 Night Central America
PORTS
Bridgetown; Rodney Bay, St. Lucia; The Pitons; Scarborough, Tobago; Port Eliza... Balboa - Fuerte Amador
SAIL DATE: Dec 04, 2026 - Dec 20, 2026
Interior
not available
Oceanview
$4099 $256/night
Balcony
$6519 $407/night
Suite
$8999 $562/night
15 Night Caribbean
PORTS
Bridgetown; Anse Mitan; Pigeon Island, St. Lucia; Pigeon Island, St. Lucia; Castries; The... Oranjestad
SAIL DATE: Nov 27, 2026 - Dec 12, 2026
Interior
not available
Oceanview
$4099 $273/night
Balcony
$6519 $434/night
Suite
$8999 $599/night
15 Night Southern Europe
PORTS
Venice, Italy; Venice, Italy; Zadar, Croatia; Dubrovnik; Dubrovnik; Messina (Taormina) Ital... Barcelona
SAIL DATE: Jan 04, 2026 - Jan 19, 2026
Interior
not available
Oceanview
$4196 $279/night
Balcony
$6976 $465/night
Suite
$10016 $667/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
16 Night Western Mediterranean
PORTS
Civitavecchia; Livorno (Florence & Pisa), Italy; Livorno (Florence & Pisa), Italy... Barcelona
SAIL DATE: Jan 12, 2026 - Jan 28, 2026
Interior
not available
Oceanview
$4799 $299/night
Balcony
$7759 $484/night
Suite
$10989 $686/night
16 Night Western Mediterranean
PORTS
Barcelona; Barcelona; Valencia, Spain; Cartagena, Spain; Gibraltar (U.K.); Malaga; Mal... Civitavecchia
SAIL DATE: Jan 19, 2026 - Feb 04, 2026
Interior
not available
Oceanview
$4799 $299/night
Balcony
$7759 $484/night
Suite
$10989 $686/night
16 Night Western Mediterranean
PORTS
Civitavecchia; Livorno (Florence & Pisa), Italy; Livorno (Florence & Pisa), Italy... Barcelona
SAIL DATE: Feb 20, 2026 - Mar 08, 2026
Interior
not available
Oceanview
$4799 $299/night
Balcony
$7759 $484/night
Suite
$13029 $814/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!