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.
7 Night Caribbean
PORTS
Philipsburg, Saint-Martin; St. John's, Antigua; Road Bay, Anguilla; Soper's... Philipsburg, Saint-Martin
SAIL DATE: Jan 31, 2026 - Feb 07, 2026
Interior
not available
Oceanview
$3299 $471/night
Balcony
not available
Suite
not available
20 Night Caribbean
PORTS
Lisbon; Funchal, Madeira; Bridgetown; Anse Mitan; Pigeon Island, St. Lucia; Pigeon Island,... Bridgetown
SAIL DATE: Nov 14, 2026 - Dec 04, 2026
Interior
not available
Oceanview
$4199 $209/night
Balcony
$6199 $309/night
Suite
$8799 $439/night
22 Night Caribbean
PORTS
Bridgetown; Basseterre; Iles Des Saintes (West Indies); Roseau; Fort-de-France; Mayreau, Grena... Lisbon
SAIL DATE: Mar 21, 2026 - Apr 12, 2026
Interior
not available
Oceanview
$4499 $204/night
Balcony
not available
Suite
$9999 $454/night
14 Night Caribbean
PORTS
Lisbon; Bridgetown
SAIL DATE: Nov 04, 2025 - Nov 18, 2025
Interior
not available
Oceanview
$2999 $214/night
Balcony
not available
Suite
not available
25 Night Caribbean
PORTS
Lisbon; Bridgetown; Port Elizabeth, Bequia, Grenadines; Mayreau, Grenadines; St. George... Colon, Panama
SAIL DATE: Nov 04, 2025 - Nov 29, 2025
Interior
not available
Oceanview
$6399 $255/night
Balcony
not available
Suite
not available
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
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
7 Night Panama Canal
PORTS
Puerto Caldera, Costa Rica; Punta Leona; Puerto Quepos, Costa Rica; Puerto Jim... Balboa - Fuerte Amador
SAIL DATE: Feb 09, 2027 - Feb 16, 2027
Interior
not available
Oceanview
$2099 $299/night
Balcony
$3359 $479/night
Suite
$4599 $657/night
14 Night Caribbean
PORTS
Bridgetown; Basseterre; St. John's, Newfoundland; Iles Des Saintes (West Indies); Roseau;... Bridgetown
SAIL DATE: Mar 07, 2026 - Mar 21, 2026
Interior
not available
Oceanview
$4099 $292/night
Balcony
not available
Suite
$9999 $714/night
10 Night Caribbean
PORTS
Bridgetown; Mayreau, Grenadines; Roseau; Anse Mitan; Deshaies, Guadeloupe;... Philipsburg, Saint-Martin
SAIL DATE: Jan 04, 2026 - Jan 14, 2026
Interior
not available
Oceanview
$3058 $305/night
Balcony
not available
Suite
not available
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!