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 Transatlantic
PORTS
Lisbon; Funchal, Madeira; Bridgetown
SAIL DATE: Nov 14, 2026 - Nov 27, 2026
Interior
not available
Oceanview
$2299 $176/night
Balcony
$3199 $246/night
Suite
$2299 $176/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
$2034 $184/night
Balcony
$3233 $293/night
Suite
$7769 $706/night
15 Night Transatlantic
PORTS
Bridgetown; Lisbon
SAIL DATE: Mar 28, 2026 - Apr 12, 2026
Interior
not available
Oceanview
$2899 $193/night
Balcony
not available
Suite
$5499 $366/night
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
$3299 $471/night
Balcony
not available
Suite
not available
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
22 Night Caribbean
PORTS
Bridgetown; Basseterre; Iles Des Saintes (West Indies); Roseau; Fort-de-France; Mayreau, Grena... Lisbon
SAIL DATE: Mar 21, 2026 - Apr 12, 2026
Interior
not available
Oceanview
$4499 $204/night
Balcony
not available
Suite
$9999 $454/night
14 Night Caribbean
PORTS
Lisbon; Bridgetown
SAIL DATE: Nov 04, 2025 - Nov 18, 2025
Interior
not available
Oceanview
$2999 $214/night
Balcony
not available
Suite
not available
8 Night Western Mediterranean
PORTS
Venice, Italy; Venice, Italy; Zadar, Croatia; Dubrovnik; Dubrovnik; Messina (Taormina)... Civitavecchia
SAIL DATE: Mar 23, 2026 - Mar 31, 2026
Interior
not available
Oceanview
$1814 $226/night
Balcony
$2606 $325/night
Suite
$6259 $782/night
25 Night Transatlantic
PORTS
Bridgetown; Lisbon; Tangier, Morocco; Malaga; Malaga; Cartagena, Spain; Valencia, Spain; Pa... Barcelona
SAIL DATE: Mar 28, 2026 - Apr 22, 2026
Interior
not available
Oceanview
$5499 $219/night
Balcony
not available
Suite
not available
7 Night South Pacific
PORTS
Papeete, Tahiti; Moorea; Raiatea; Raiatea; Motu Mahaea (Tahaa); Bora Bora; Bora Bora;... Papeete, Tahiti
SAIL DATE: Dec 11, 2025 - Dec 18, 2025
Interior
not available
Oceanview
$1759 $251/night
Balcony
$2606 $372/night
Suite
$6419 $917/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!