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, Antigua; Philipsburg, Saint-Martin
SAIL DATE: Dec 05, 2026 - Dec 19, 2026
Interior
not available
Oceanview
$2499 $178/night
Balcony
not available
Suite
$3099 $221/night
21 Night Europe
PORTS
Lisbon; St. John's, Newfoundland; Philipsburg, Saint-Martin; Falmouth, Corn... Philipsburg, Saint-Martin
SAIL DATE: Dec 05, 2026 - Dec 26, 2026
Interior
not available
Oceanview
$4399 $209/night
Balcony
not available
Suite
$5799 $276/night
16 Night Central America
PORTS
Bridgetown; Rodney Bay, St. Lucia; The Pitons; Scarborough, Tobago; Port Eliza... Balboa - Fuerte Amador
SAIL DATE: Dec 04, 2026 - Dec 20, 2026
Interior
not available
Oceanview
$4099 $256/night
Balcony
$6519 $407/night
Suite
$8999 $562/night
14 Night N-A
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Dec 06, 2026 - Dec 20, 2026
Interior
not available
Oceanview
$3999 $285/night
Balcony
$6419 $458/night
Suite
$8899 $635/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Gustavia; Charlestown; Roseau; Mayreau, Grenadin... Philipsburg, Saint-Martin
SAIL DATE: Dec 26, 2026 - Jan 09, 2027
Interior
not available
Oceanview
$4099 $292/night
Balcony
not available
Suite
$5799 $414/night
14 Night N-A
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Dec 13, 2026 - Dec 27, 2026
Interior
not available
Oceanview
$4099 $292/night
Balcony
$6519 $465/night
Suite
$8999 $642/night
8 Night Panama Canal
PORTS
Balboa - Fuerte Amador; Isla Parida, Panama; Puerto Jimenez (Golfo Dulce),... Puerto Caldera, Costa Rica
SAIL DATE: Dec 20, 2026 - Dec 28, 2026
Interior
not available
Oceanview
$2299 $287/night
Balcony
$3559 $444/night
Suite
$4799 $599/night
14 Night Caribbean
PORTS
Philipsburg, Saint-Martin; Falmouth, Cornwall, England; Gustavia; Road Bay,... Philipsburg, Saint-Martin
SAIL DATE: Dec 19, 2026 - Jan 02, 2027
Interior
not available
Oceanview
$4299 $307/night
Balcony
not available
Suite
$5999 $428/night
14 Night N-A
PORTS
San Juan; St Georges; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; Iles Des Sain... San Juan
SAIL DATE: Dec 20, 2026 - Jan 03, 2027
Interior
not available
Oceanview
$4399 $314/night
Balcony
$6819 $487/night
Suite
$9299 $664/night
14 Night N-A
PORTS
San Juan; Cruz Bay, St. John; Gustavia; Basseterre; Philipsburg, Saint-Martin; Jost Van Dyke... San Juan
SAIL DATE: Dec 27, 2026 - Jan 10, 2027
Interior
not available
Oceanview
$4499 $321/night
Balcony
$6919 $494/night
Suite
$9399 $671/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!