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
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
$725 $103/night
Balcony
$1229 $175/night
Suite
$4845 $692/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
$1919 $119/night
Balcony
$3103 $193/night
Suite
$10989 $686/night
7 Night Western Mediterranean
PORTS
Malaga; Malaga; Gibraltar (U.K.); Cartagena, Spain; Valencia, Spain; Palma de Mallorca; Ba... Barcelona
SAIL DATE: Dec 13, 2025 - Dec 20, 2025
Interior
not available
Oceanview
$2656 $379/night
Balcony
$4096 $585/night
Suite
$5616 $802/night
7 Night South Pacific
PORTS
Papeete, Tahiti; Fakarava, Tuamotu Archipelago; Rangiroa, French Polynesia; Bora Bora... Papeete, Tahiti
SAIL DATE: Apr 16, 2026 - Apr 23, 2026
Interior
not available
Oceanview
$931 $133/night
Balcony
$1609 $229/night
Suite
$6072 $867/night
7 Night Western Mediterranean
PORTS
Malaga; Malaga; Gibraltar (U.K.); Cartagena, Spain; Valencia, Spain; Palma de Mallorca; Ba... Barcelona
SAIL DATE: Nov 14, 2025 - Nov 21, 2025
Interior
not available
Oceanview
$962 $137/night
Balcony
$1538 $219/night
Suite
$5302 $757/night
9 Night Western Mediterranean
PORTS
Barcelona; Barcelona; Valencia, Spain; Cartagena, Spain; Gibraltar (U.K.); Malaga; Malaga;... Barcelona
SAIL DATE: Jan 19, 2026 - Jan 28, 2026
Interior
not available
Oceanview
$1279 $142/night
Balcony
$1927 $214/night
Suite
$6529 $725/night
14 Night Transatlantic
PORTS
Philipsburg, Saint-Martin; Ponta Delgada, Azores; Lisbon
SAIL DATE: Apr 04, 2026 - Apr 18, 2026
Interior
not available
Oceanview
$2369 $169/night
Balcony
not available
Suite
$2969 $212/night
7 Night North America
PORTS
New York City; St Georges; St Georges; San Juan
SAIL DATE: Oct 19, 2025 - Oct 26, 2025
Interior
not available
Oceanview
$1210 $172/night
Balcony
$2710 $387/night
Suite
$4710 $672/night
14 Night Transatlantic
PORTS
Lisbon; St. John's, Antigua; Philipsburg, Saint-Martin
SAIL DATE: Dec 05, 2026 - Dec 19, 2026
Interior
not available
Oceanview
$2499 $178/night
Balcony
not available
Suite
$3099 $221/night
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
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!