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.
22 Night Transatlantic
PORTS
Philipsburg, Saint-Martin; Ponta Delgada, Azores; Lisbon; Cadiz & Seville; Gibraltar... Barcelona
SAIL DATE: Apr 04, 2026 - Apr 26, 2026
Interior
not available
Oceanview
$5299 $240/night
Balcony
not available
Suite
$6839 $310/night
25 Night Northern Europe
PORTS
Lisbon; Cadiz & Seville; Gibraltar (U.K.); Malaga; Almeria, Spain; Cartagena, Spa... Venice, Italy
SAIL DATE: Apr 18, 2026 - May 13, 2026
Interior
not available
Oceanview
$8799 $351/night
Balcony
not available
Suite
not available
55 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla;... Philipsburg, Saint-Martin
SAIL DATE: Jan 04, 2026 - Feb 28, 2026
Interior
not available
Oceanview
$20899 $379/night
Balcony
not available
Suite
$25799 $469/night
28 Night Europe
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Road Bay, Anguilla; Sopers Hole (F... Oranjestad
SAIL DATE: Jan 04, 2026 - Feb 01, 2026
Interior
not available
Oceanview
$10099 $360/night
Balcony
not available
Suite
$12899 $460/night
23 Night Europe
PORTS
Venice, Italy; Rovinj, Croatia; Split, Croatia; Dubrovnik; Dubrovnik; Kotor, Montenegro; Giard... Lisbon
SAIL DATE: Oct 15, 2026 - Nov 07, 2026
Interior
not available
Oceanview
$8399 $365/night
Balcony
not available
Suite
$10969 $476/night
24 Night Europe
PORTS
Barcelona; Palamos, Spain; Sanary-Sur-Mer, France; Monte Carlo; Cannes; PORTOFERRAIO (E... Venice, Italy
SAIL DATE: Jun 30, 2026 - Jul 24, 2026
Interior
not available
Oceanview
$8999 $374/night
Balcony
not available
Suite
$11889 $495/night
25 Night Europe
PORTS
Reykjavik, Iceland; Prince Christian Sound East; Qaqortoq, Greenland; Narsaq; Nanortalik, Gr... Montreal
SAIL DATE: Aug 31, 2026 - Sep 25, 2026
Interior
not available
Oceanview
$9399 $375/night
Balcony
$13899 $555/night
Suite
$20689 $827/night
25 Night Western Mediterranean
PORTS
Civitavecchia; Syracuse; Gozo Island, Malta; Valletta; Porto Empedocle, Sicily; Trapani, Sicil... Lisbon
SAIL DATE: May 28, 2026 - Jun 22, 2026
Interior
not available
Oceanview
$10399 $415/night
Balcony
not available
Suite
$12749 $509/night
25 Night Canada - New England
PORTS
Boston; Rockland, Maine; Portland; Halifax; Sydney; Cap Aux Meules; Gaspe, Quebec; Quebec Ci... Montreal
SAIL DATE: Sep 14, 2026 - Oct 09, 2026
Interior
not available
Oceanview
$11299 $451/night
Balcony
$15799 $631/night
Suite
$26079 $1043/night
25 Night Canada - New England
PORTS
Montreal; Quebec City, Quebec; Baie-Comeau, Quebec; Cap Aux Meules; St Pierre & Miquelon;... Boston
SAIL DATE: Sep 25, 2026 - Oct 20, 2026
Interior
not available
Oceanview
$11299 $451/night
Balcony
$15799 $631/night
Suite
$26079 $1043/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!