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Windstar Cruises to Caribbean - All 2022/2023

Save up to 75% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - All 2022/2023, we are able to offer you unbeatable prices and unparalleled value. With cruise line volume buys plus our low everyday prices you can save up to 75% versus the brochure price! Once you have found the discounted Windstar cruise of your choice, please call our cruise consultants to book your vacation and save money with our first-rate personalized service! Book your Windstar cruise today with AffordableTours.com, your discounted cruise headquarters.

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Sail Date Cruise Line Ship Destination Departs Length Price You Save Discounts
23 reviews
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WindstarWind SurfCaribbean - SouthernBridgetownColon16 NightsBocas Del Toro, Panama | Bridgetown, Barbados, Barbados | Cartagena, Colombia, Colombia | Colon, Panama | Kralendijk, Bonaire, Bonair | Man-O-War Bay, Charlotteville, Trinidad And Tobago | Mayreau, Saint Vincent And The Grenadines | Oranjestad, Aruba, Aruba | Puerto Limon, Costa Rica | San Blas Islands, Panama, Panama | Santa Marta, Colombia | Soufriere, Saint Lucia | Willemstad, Curacao, Curacao$4,199
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
8 reviews
Itinerary Map/Ship Image
WindstarWind StarPanama CanalPuerto CalderaBridgetown18 NightsBequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Cartagena, Colombia, Colombia | Colon, Panama | Fuerte Amador, Panama City, Panama | Isla Parida, Panama | Kralendijk, Bonaire, Bonair | Mayreau, Saint Vincent And The Grenadines | Oranjestad, Aruba, Aruba | Puerto Caldera, San Jose, Costa Rica | Puerto Jimenez, Golfo Dulce, Costa Rica | Quepos, Manuel Antonio Natl Pk, Costa Rica | St. GeorgeS, Grenada, Grenada | Willemstad, Curacao, Curacao$5,599
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
8 reviews
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WindstarWind StarPanama CanalPuerto CalderaBridgetown28 NightsAnse Mitan, Martinique, Martinique | Basseterre, St. Kitts, Saint Kitts - Nevis | Bequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Cartagena, Colombia, Colombia | Colon, Panama | Deshaies, Guadeloupe | Falmouth Harbour, Antigua, Antigua And Barbuda | Fuerte Amador, Panama City, Panama | Gustavia, St. Barthelemy, St. Barthelemy | Isla Parida, Panama | Kralendijk, Bonaire, Bonair | Mayreau, Saint Vincent And The Grenadines | Oranjestad, Aruba, Aruba | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | Puerto Caldera, San Jose, Costa Rica | Puerto Jimenez, Golfo Dulce, Costa Rica | Quepos, Manuel Antonio Natl Pk, Costa Rica | Soufriere, Saint Lucia | St. GeorgeS, Grenada, Grenada | Willemstad, Curacao, Curacao$7,599
Up To $1000 Onboard Credit
Onboard Credit!
2 reviews
Itinerary Map/Ship Image
WindstarStar LegendPanama CanalPhilipsburgPhilipsburg7 NightsColon, Panama | Fuerte Amador, Panama City, Panama | Isla Parida, Panama | Puerto Caldera, San Jose, Costa Rica | Puerto Jimenez, Golfo Dulce, Costa Rica | Quepos, Manuel Antonio Natl Pk, Costa Rica$2,299
Up To $250 Onboard Credit
 

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23 reviews
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WindstarWind SurfCaribbeanBridgetownOranjestad8 NightsBridgetown, Barbados, Barbados | Kralendijk, Bonaire, Bonair | Man-O-War Bay, Charlotteville, Trinidad And Tobago | Mayreau, Saint Vincent And The Grenadines | Oranjestad, Aruba, Aruba | Soufriere, Saint Lucia | St. GeorgeS, Grenada, Grenada | Willemstad, Curacao, Curacao$2,599
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
2 reviews
Itinerary Map/Ship Image
WindstarStar LegendCaribbeanPhilipsburgPhilipsburg14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | St. George's | St. Maarten | Virgin Gorda$4,199
Up To $500 Onboard Credit
Suite!
8 reviews
Itinerary Map/Ship Image
WindstarWind StarCentral AmericaColonBridgetown11 NightsBequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Cartagena, Colombia, Colombia | Colon, Panama | Kralendijk, Bonaire, Bonair | Mayreau, Saint Vincent And The Grenadines | Oranjestad, Aruba, Aruba | St. GeorgeS, Grenada, Grenada | Willemstad, Curacao, Curacao$3,199
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
2 reviews
Itinerary Map/Ship Image
WindstarStar LegendCaribbeanPhilipsburgPhilipsburg14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | St. George's | St. Maarten | Virgin Gorda$4,699
Up To $500 Onboard Credit
Suite!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbeanOranjestadColon8 NightsBocas Del Toro, Panama | Cartagena, Colombia, Colombia | Colon, Panama | Oranjestad, Aruba, Aruba | Puerto Limon, Costa Rica | Santa Marta, Colombia$2,699
Up To $300 Onboard Credit
Onboard Credit!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbeanOranjestadCozumel16 NightsBelize City, Belize | Bocas Del Toro, Panama | Cartagena, Colombia, Colombia | Colon, Panama | Costa Maya, Mexico | Cozumel, Mexico | Oranjestad, Aruba, Aruba | Puerto Limon, Costa Rica | Rada El Cove, Isla San Andres, Colombia | Roatan, Honduras | Santa Marta, Colombia$3,999
Up To $500 Onboard Credit
 
2 reviews
Itinerary Map/Ship Image
WindstarStar LegendCaribbeanPhilipsburgPhilipsburg14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | St. George's | St. Maarten | Virgin Gorda$4,699
Up To $500 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternColonPhilipsburg19 NightsBelize City, Belize | Bocas Del Toro, Panama | Colon, Panama | Costa Maya, Mexico | Cozumel, Mexico | Georgetown, Grand Cayman, Cayman Islands | Great Harbour, Jost Van Dyke, British Virgin Islands | La Romana, Dominican Republic | Philipsburg, St. Maarten, Saint Maarten | Port Antonio, Jamaica | Rada El Cove, Isla San Andres, Colombia | Roatan, Honduras | Santo Domingo, Dominican Republic | Virgin Gorda, Bvi, British Virgin Islands | West End, Cayman Brac, Cayman Islands$4,699
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
8 reviews
Itinerary Map/Ship Image
WindstarWind StarCaribbean - SouthernBridgetownBridgetown10 NightsAnse Mitan, Martinique, Martinique | Basseterre, St. Kitts, Saint Kitts - Nevis | Bridgetown, Barbados, Barbados | Deshaies, Guadeloupe | Falmouth Harbour, Antigua, Antigua And Barbuda | Gustavia, St. Barthelemy, St. Barthelemy | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | Soufriere, Saint Lucia$3,199
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
2 reviews
Itinerary Map/Ship Image
WindstarStar LegendCaribbeanPhilipsburgPhilipsburg14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | St. George's | St. Maarten | Virgin Gorda$4,799
Up To $500 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternCozumelPhilipsburg11 NightsCozumel, Mexico | Georgetown, Grand Cayman, Cayman Islands | Great Harbour, Jost Van Dyke, British Virgin Islands | La Romana, Dominican Republic | Philipsburg, St. Maarten, Saint Maarten | Port Antonio, Jamaica | Santo Domingo, Dominican Republic | Virgin Gorda, Bvi, British Virgin Islands | West End, Cayman Brac, Cayman Islands$3,399
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - WesternCozumelPhilipsburg18 NightsBasseterre, St. Kitts, Saint Kitts - Nevis | Charlestown, Saint Kitts - Nevis | Cozumel, Mexico | Georgetown, Grand Cayman, Cayman Islands | Great Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | La Romana, Dominican Republic | Les Saintes, Guadeloupe, Guadeloupe | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | Port Antonio, Jamaica | Roseau, Dominica, Dominica | Santo Domingo, Dominican Republic | Virgin Gorda, Bvi, British Virgin Islands | West End, Cayman Brac, Cayman Islands$4,699
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
2 reviews
Itinerary Map/Ship Image
WindstarStar LegendCaribbeanPhilipsburgPhilipsburg14 NightsBasseterre | Bequia | Gustavia | Jost Van Dyke, Great Harbour | Les Saintes | Little Bay | Pigeon Island | Soper's Hole | St. George's | St. Maarten | Virgin Gorda$6,799
Up To $750 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg7 NightsBasseterre, St. Kitts, Saint Kitts - Nevis | Charlestown, Saint Kitts - Nevis | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | Roseau, Dominica, Dominica$2,499
Up To $250 Onboard Credit
Onboard Credit!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternPhilipsburgPhilipsburg14 NightsBasseterre, St. Kitts, Saint Kitts - Nevis | Charlestown, Saint Kitts - Nevis | Falmouth Harbour, Antigua, Antigua And Barbuda | Great Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | Roseau, Dominica, Dominica | SoperS Hole, Tortola, Bvi, British Virgin Islands | Virgin Gorda, Bvi, British Virgin Islands$4,299
Shipboard Credit Per Person ($100)
Shipboard Credit Per Person ($100)
8 reviews
Itinerary Map/Ship Image
WindstarWind StarCaribbean - SouthernBridgetownBridgetown7 NightsAnse Mitan, Martinique, Martinique | Bequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Mayreau, Saint Vincent And The Grenadines | Pigeon Island, St. Lucia, Saint Lucia | St. GeorgeS, Grenada, Grenada$2,499
Up To $250 Onboard Credit
Onboard Credit!

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