Windstar Star Legend
7-Night Caribbean
Ports of call: Anses D'arlet, Rodney Bay, Sunset Cruising Pitons, Casablanca and 3 more
- Leaves in 19 days
Last Minute Windstar Cruises
Every Windstar Cruises cruise leaving in the next 90 days, from any port, cheapest first.
82 cruises from $2,419 per person Updated Nov 8, 2026, 4:04 a.m. ET
82 Windstar sailings leave in the next 90 days, on 8 ships from 16 ports. The cheapest is the 7-Night Caribbean on Star Legend, leaving Bridgetown (Barbados) on Fri, Nov 27, 2026, from $2,419 per person. Most leave from Papeete (French Polynesia), San Juan (Puerto Rico) and Philipsburg (Sint Maarten).
Deals
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Filter and sort 82 cruises
Windstar Wind Surf
7-Night Caribbean
Ports of call: Falmouth Harbour, Road Bay, Sopers Hole, Jost Van Dyke and 2 more
- Leaves in 55 days
Windstar Star Breeze
7-Night Tahiti
Ports of call: Moorea, Raiatea, Tahaa, Bora Bora and 1 more
- Leaves in 25 days
Windstar Star Explorer
7-Night Mediterranean
Ports of call: Nice, Rapallo, Livorno
- Leaves in 68 days
Windstar Star Legend
7-Night Costa Rica
Ports of call: Quepos, Puerto Jimenez, Isla Parida, Balboa and 1 more
- Leaves in 79 days
Windstar Star Pride
7-Night Caribbean
Ports of call: St. Georges, Bequia, Mayreau, Deshaies and 1 more
- Leaves in 56 days
Windstar Wind Surf
7-Night Caribbean
Ports of call: Jeju Island South Korea, Les Saintes, Mayreau, Roseau and 2 more
- Leaves in 62 days
Windstar Star Breeze
7-Night Tahiti
Ports of call: Moorea, Raiatea, Tahaa, Bora Bora and 1 more
- Leaves in 32 days
Windstar Star Pride
7-Night Caribbean
Ports of call: St. Georges, Bequia, Mayreau, Deshaies and 1 more
- Leaves in 28 days
Windstar Star Pride
7-Night Caribbean
Ports of call: St. Georges, Bequia, Mayreau, Les Saintes and 1 more
- Leaves in 14 days
Windstar Star Legend
7-Night Costa Rica
Ports of call: Balboa, Panama Canal, Balboa, Isla Parida and 2 more
- Leaves in 86 days
Windstar Star Legend
8-Night Costa Rica
Ports of call: Quepos, Puerto Jimenez, Balboa, Panama Canal and 1 more
- Leaves in 50 days
Windstar Star Legend
8-Night Costa Rica
Ports of call: Cartagena, Bocas Del Toro, San Blas Islands, Panama Canal
- Leaves in 34 days
Windstar Wind Surf
7-Night Caribbean
Ports of call: Gustavia, Falmouth Harbour, Road Bay, Jost Van Dyke and 3 more
- Leaves in 41 days
Windstar Wind Surf
7-Night Caribbean
Ports of call: Road Bay, Jost Van Dyke, Sopers Hole, Jost Van Dyke and 3 more
- Leaves in 83 days
Windstar Star Legend
8-Night Caribbean
Ports of call: Rodney Bay, Sunset Cruising Pitons, Bequia, Mayreau and 2 more
- Leaves in 26 days
Windstar Wind Surf
7-Night Caribbean
Ports of call: Jeju Island South Korea, Roseau, Mayreau, Les Saintes and 2 more
- Leaves in 76 days
Windstar Star Legend
7-Night Costa Rica
Ports of call: Balboa, Panama Canal, Balboa, Isla Parida and 2 more
- Leaves in 58 days
Windstar Star Breeze
7-Night Tahiti
Ports of call: Raiatea, Tahaa, Bora Bora, Huahine
- Leaves in 60 days
Windstar Wind Star
7-Night Costa Rica
Ports of call: Quepos, Puerto Jimenez, Isla Parida, Balboa and 1 more
- Leaves in 34 days
Windstar Wind Star
7-Night Costa Rica
Ports of call: Balboa, Panama Canal, Balboa, Isla Parida and 2 more
- Leaves in 55 days
Windstar Star Legend
8-Night Costa Rica
Ports of call: Isla Parida, Puerto Jimenez, Quepos, Curu and 1 more
- Leaves in 42 days
Windstar Star Pride
7-Night Caribbean
Ports of call: Cruz Bay, Gustavia, Port of Basseterre, Philipsburg and 2 more
- Leaves in 49 days
Windstar Star Explorer
8-Night Mediterranean
Ports of call: Zadar, Dubrovnik, Messina, Naples
- Leaves in 83 days
Windstar Cruises last minute deals by price per night
Fare divided by nights, so a cheap short cruise and a long one compare fairly.
- 115-Night CaribbeanWindstar · Star Legend · Nov 27 from Bridgetown (Barbados)$314 a night$4,709 for 15 nights
- 222-Night TransatlanticWindstar · Star Legend · Nov 12 from Malaga (Spain)$322 a night$7,084 for 22 nights
- 316-Night CaribbeanWindstar · Star Legend · Dec 4 from Bridgetown (Barbados)$324 a night$5,182 for 16 nights
- 47-Night CaribbeanWindstar · Star Legend · Nov 27 from Bridgetown (Barbados)$346 a night$2,419 for 7 nights
- 517-Night TahitiWindstar · Star Breeze · Dec 28 from Papeete (French Polynesia)$347 a night$5,897 for 17 nights
Where Windstar sails in the next 90 days
Where these Windstar cruises leave from
Papeete (French Polynesia) (19), San Juan (Puerto Rico) (11), Philipsburg (Sint Maarten) (8), Santa Cruz de Tenerife (Spain) (6), Colon (Panama) (6), Bridgetown (Barbados) (5), Puerto Caldera (Costa Rica) (5), Ha Long Bay (Vietnam) (4), Bangkok (Thailand) (4), Barcelona (Spain) (4), Venice (Italy) (3), Malaga (Spain) (2), Port of Oranjestad (Aruba) (2), Lisbon (Portugal) (1), Balboa (Panama) (1), Phuket (Thailand) (1). Use the "Leaving from" filter above to see one port's sailings.
Windstar offers on Cruisebound right now
Cruisebound's own promotions, as it lists them. Terms vary by sailing and cabin, so read them on Cruisebound before you count on one.
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