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
14 Night Transatlantic
PORTS
Lisbon; Bridgetown
SAIL DATE: Nov 10, 2026 - Nov 24, 2026
Interior
not available
Oceanview
$2499 $178/night
Balcony
not available
Suite
not available
14 Night N-A
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Nov 08, 2026 - Nov 22, 2026
Interior
not available
Oceanview
$3999 $285/night
Balcony
$6419 $458/night
Suite
$8899 $635/night
14 Night N-A
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 29, 2026 - Dec 13, 2026
Interior
not available
Oceanview
$3999 $285/night
Balcony
$6419 $458/night
Suite
$8899 $635/night
14 Night N-A
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 15, 2026 - Nov 29, 2026
Interior
not available
Oceanview
$3999 $285/night
Balcony
$6419 $458/night
Suite
$8899 $635/night
14 Night N-A
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Nov 22, 2026 - Dec 06, 2026
Interior
not available
Oceanview
$3999 $285/night
Balcony
$6419 $458/night
Suite
$8899 $635/night
10 Night Western Mediterranean
PORTS
Barcelona; Cartagena, Spain; Malaga; Malaga; Gibraltar (U.K.); Cadiz & Seville; Cadiz &a... Lisbon
SAIL DATE: Nov 04, 2026 - Nov 14, 2026
Interior
not available
Oceanview
$3599 $359/night
Balcony
$5099 $509/night
Suite
$6799 $679/night
10 Night Canary Islands
PORTS
Santa Cruz De Tenerife, Canary Islands; Lanzarote; Funchal, Ma... Santa Cruz De Tenerife, Canary Islands
SAIL DATE: Nov 17, 2026 - Nov 27, 2026
Interior
not available
Oceanview
$3499 $349/night
Balcony
not available
Suite
$6499 $649/night
10 Night Canary Islands
PORTS
Santa Cruz De Tenerife, Canary Islands; Puerto Del Rosario-Fue... Santa Cruz De Tenerife, Canary Islands
SAIL DATE: Nov 27, 2026 - Dec 07, 2026
Interior
not available
Oceanview
$3499 $349/night
Balcony
not available
Suite
$6499 $649/night
11 Night South Pacific
PORTS
Papeete, Tahiti; Fakarava, Tuamotu Archipelago; Omoa; Atuona, Hiva Oa, Marquesas; Tai... Papeete, Tahiti
SAIL DATE: Nov 12, 2026 - Nov 23, 2026
Interior
not available
Oceanview
$4699 $427/night
Balcony
$7119 $647/night
Suite
$9759 $887/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!