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.
14 Night Transatlantic
PORTS
Lisbon; St. John's, Newfoundland; Philipsburg, Saint-Martin
SAIL DATE: Nov 18, 2025 - Dec 02, 2025
Interior
not available
Oceanview
$2899 $207/night
Balcony
not available
Suite
$3499 $249/night
7 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 30, 2025 - Dec 07, 2025
Interior
not available
Oceanview
$1538 $219/night
Balcony
$2231 $318/night
Suite
$5299 $757/night
19 Night Europe
PORTS
Lisbon; St. John's, Newfoundland; Philipsburg, Saint-Martin; Sopers Hole (F... Philipsburg, Saint-Martin
SAIL DATE: Nov 18, 2025 - Dec 07, 2025
Interior
not available
Oceanview
$4199 $221/night
Balcony
not available
Suite
$5499 $289/night
14 Night Caribbean Eastern
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Nov 23, 2025 - Dec 07, 2025
Interior
not available
Oceanview
$3819 $272/night
Balcony
$5934 $423/night
Suite
$8419 $601/night
20 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Mar... Puerto Caldera, Costa Rica
SAIL DATE: Nov 30, 2025 - Dec 20, 2025
Interior
not available
Oceanview
$5999 $299/night
Balcony
$9674 $483/night
Suite
$13399 $669/night
14 Night Caribbean Eastern
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Nov 09, 2025 - Nov 23, 2025
Interior
not available
Oceanview
$4199 $299/night
Balcony
$6614 $472/night
Suite
$9099 $649/night
13 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Martin; Jost Van... Colon, Panama
SAIL DATE: Nov 30, 2025 - Dec 13, 2025
Interior
not available
Oceanview
$4099 $315/night
Balcony
$6514 $501/night
Suite
$8999 $692/night
14 Night Caribbean Eastern
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 16, 2025 - Nov 30, 2025
Interior
not available
Oceanview
$4499 $321/night
Balcony
$6614 $472/night
Suite
$9099 $649/night
14 Night Caribbean Eastern
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 02, 2025 - Nov 16, 2025
Interior
not available
Oceanview
$4699 $335/night
Balcony
$7114 $508/night
Suite
$9599 $685/night
15 Night Western Mediterranean
PORTS
Civitavecchia; PORTOFERRAIO (ELBA); Monte Carlo; Cannes; Toulon, France; Palamos, Spain; Barce... Lisbon
SAIL DATE: Nov 03, 2025 - Nov 18, 2025
Interior
not available
Oceanview
$5799 $386/night
Balcony
not available
Suite
$6649 $443/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!