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.
8 Night N-A
PORTS
Boston; Hamilton; Hamilton; St Georges; St Georges; San Juan
SAIL DATE: Oct 20, 2026 - Oct 28, 2026
Interior
not available
Oceanview
$2399 $299/night
Balcony
$3659 $457/night
Suite
$4899 $612/night
19 Night Caribbean
PORTS
Montreal; Quebec City, Quebec; Quebec City, Quebec; Gaspe, Quebec; Cap Aux Meules; Sydney; H... San Juan
SAIL DATE: Oct 09, 2026 - Oct 28, 2026
Interior
not available
Oceanview
$6099 $321/night
Balcony
$9439 $496/night
Suite
$12569 $661/night
11 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Falmouth, Cornwall, England; Iles Des Sa... San Juan
SAIL DATE: Oct 28, 2026 - Nov 08, 2026
Interior
not available
Oceanview
$3599 $327/night
Balcony
$6019 $547/night
Suite
$8499 $772/night
18 Night Europe
PORTS
Athens, Greece; Delphi; Corfu; Argostoli, Kefalonia, Greece; Messina (Taormina) Italy; Trapani... Lisbon
SAIL DATE: Oct 27, 2026 - Nov 14, 2026
Interior
not available
Oceanview
$5999 $333/night
Balcony
$8839 $491/night
Suite
$12059 $669/night
13 Night Western Mediterranean
PORTS
Civitavecchia; Monte Carlo; Sanary-Sur-Mer, France; Palamos, Spain; Barcelona; Palma de Mallor... Lisbon
SAIL DATE: Oct 25, 2026 - Nov 07, 2026
Interior
not available
Oceanview
$4999 $384/night
Balcony
not available
Suite
$6849 $526/night
14 Night South Pacific
PORTS
Papeete, Tahiti; Moorea; Raiatea; Raiatea; Motu Mahaea (Tahaa); Bora Bora; Bora Bora;... Papeete, Tahiti
SAIL DATE: Oct 08, 2026 - Oct 22, 2026
Interior
not available
Oceanview
$5299 $378/night
Balcony
$9399 $671/night
Suite
$11639 $831/night
16 Night Mediterranean
PORTS
Istanbul; Myrina, Lemnos, Greece; Mykonos; Kusadasi (Ephesus), Turkey; Bodrum, Turkey; Sant... Barcelona
SAIL DATE: Oct 19, 2026 - Nov 04, 2026
Interior
not available
Oceanview
$6499 $406/night
Balcony
$8239 $514/night
Suite
$10419 $651/night
14 Night South Pacific
PORTS
Papeete, Tahiti; Fakarava, Tuamotu Archipelago; Rangiroa, French Polynesia; Bora Bora... Papeete, Tahiti
SAIL DATE: Oct 15, 2026 - Oct 29, 2026
Interior
not available
Oceanview
$5799 $414/night
Balcony
$8839 $631/night
Suite
$11639 $831/night
10 Night Europe
PORTS
Venice, Italy; Rovinj, Croatia; Split, Croatia; Dubrovnik; Dubrovnik; Kotor, Montenegro... Civitavecchia
SAIL DATE: Oct 15, 2026 - Oct 25, 2026
Interior
not available
Oceanview
$4299 $429/night
Balcony
not available
Suite
$5019 $501/night
7 Night South Pacific
PORTS
Papeete, Tahiti; Moorea; Raiatea; Raiatea; Motu Mahaea (Tahaa); Bora Bora; Bora Bora;... Papeete, Tahiti
SAIL DATE: Oct 29, 2026 - Nov 05, 2026
Interior
not available
Oceanview
$3199 $457/night
Balcony
$4893 $699/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!