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.
15 Night Caribbean
PORTS
Bridgetown; Anse Mitan; Pigeon Island, St. Lucia; Pigeon Island, St. Lucia; Castries; The... Oranjestad
SAIL DATE: Nov 27, 2026 - Dec 12, 2026
Interior
not available
Oceanview
$4099 $273/night
Balcony
$6519 $434/night
Suite
$8999 $599/night
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
7 Night Caribbean
PORTS
San Juan; St. George's, Grenada; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Il... San Juan
SAIL DATE: Nov 08, 2026 - Nov 15, 2026
Interior
not available
Oceanview
$2499 $357/night
Balcony
$3759 $537/night
Suite
$4999 $714/night
7 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Basseterre; Gustavia; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 15, 2026 - Nov 22, 2026
Interior
not available
Oceanview
$2499 $357/night
Balcony
$3499 $499/night
Suite
$4499 $642/night
7 Night Caribbean
PORTS
San Juan; St. George's, Grenada; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Il... San Juan
SAIL DATE: Nov 22, 2026 - Nov 29, 2026
Interior
not available
Oceanview
$2499 $357/night
Balcony
$3759 $537/night
Suite
$4999 $714/night
7 Night Caribbean
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Nov 29, 2026 - Dec 06, 2026
Interior
not available
Oceanview
$2499 $357/night
Balcony
$3759 $537/night
Suite
$4999 $714/night
17 Night South Pacific
PORTS
Papeete, Tahiti; Fakarava, Tuamotu Archipelago; Rangiroa, French Polynesia; Motu Maha... Papeete, Tahiti
SAIL DATE: Nov 23, 2026 - Dec 10, 2026
Interior
not available
Oceanview
$5999 $352/night
Balcony
$9993 $587/night
Suite
$13719 $807/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!