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Windstar Cruises to Caribbean - Southern

Save up to 40% on Windstar cruises

As a large-scale seller of Windstar Cruises to Caribbean - Southern, 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 80% 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 - EasternPhilipsburgPhilipsburg13 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 Lu$1,799
Up To $200 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 Lu$2,099
Up To $250 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 Lu$1,999
Up To $200 Onboard Credit
Onboard Credit!
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan6 NightsGreat Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten, Saint Maarten | San Juan, Puerto Rico | Virgin Gorda, Bvi, British Virgin Islands$1,099
Up To $150 Onboard Credit
 

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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$1,199
Up To $150 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 Lu$2,399
Up To $250 Onboard Credit
Onboard Credit!
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan7 NightsBequia, Saint Vincent And The Grenadines | Les Saintes, Guadeloupe, Guadeloupe | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | San Juan, Puerto Rico | St. GeorgeS, Grenada, Grenada$1,199
Up To $150 Onboard Credit
Suite!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - SouthernPhilipsburgBridgetown14 NightsBasseterre, St. Kitts, Saint Kitts - Nevis | Bridgetown, Barbados, Barbados | Falmouth Harbour, Antigua, Antigua And Barbuda | Great Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten, Saint Maarten |$2,599
Up To $300 Onboard Credit
Onboard Credit!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternPhilipsburgBridgetown21 NightsAnse Mitan, Martinique, Martinique | Basseterre, St. Kitts, Saint Kitts - Nevis | Bequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Falmouth Harbour, Antigua, Antigua And Barbuda | Great Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | L$3,699
Up To $500 Onboard Credit
 
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan7 NightsGreat Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten, Saint Maarten | San Juan, Puerto Rico | Virgin Gorda, Bvi, British Virgin Islands$1,999
Up To $200 Onboard Credit
Suite!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - EasternPhilipsburgBridgetown7 NightsBasseterre, St. Kitts, Saint Kitts - Nevis | Bridgetown, Barbados, Barbados | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | Roseau, Dominica, Dominica$1,299
Up To $150 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - SouthernPhilipsburgBridgetown14 NightsAnse Mitan, Martinique, Martinique | Basseterre, St. Kitts, Saint Kitts - Nevis | Bequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Mayreau, Saint Vincent And The$2,099
Up To $250 Onboard Credit
Onboard Credit!
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan7 NightsBequia, Saint Vincent And The Grenadines | Les Saintes, Guadeloupe, Guadeloupe | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | San Juan, Puerto Rico | St. GeorgeS, Grenada, Grenada$1,499
Up To $150 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - 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$1,399
Up To $150 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - SouthernBridgetownBridgetown14 NightsAnse Mitan, Martinique, Martinique | Bequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Falmouth Harbour, Antigua, Antigua And Barbuda | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Mayreau, Saint Vincent And$2,199
Up To $250 Onboard Credit
Onboard Credit!
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan7 NightsCharlotte Amalie, St Thomas Virgin Islands | Great Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten, Saint Maarten | San Juan, Puerto Rico | Virgin Gorda, Bvi, British Virgin Islands$1,499
Up To $150 Onboard Credit
 
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan14 NightsBequia, Saint Vincent And The Grenadines | Charlotte Amalie, St Thomas Virgin Islands | Great Harbour, Jost Van Dyke, British Virgin Islands | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Luci$2,499
Up To $250 Onboard Credit
Suite!
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - SouthernBridgetownBridgetown7 NightsBridgetown, Barbados, Barbados | Falmouth Harbour, Antigua, Antigua And Barbuda | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Pigeon Island, St. Lucia, Saint Lucia | Roseau, Dominica, Dominica$1,599
Up To $200 Onboard Credit
 
23 reviews
Itinerary Map/Ship Image
WindstarWind SurfCaribbean - SouthernBridgetownBridgetown14 NightsAnse Mitan, Martinique, Martinique | Bequia, Saint Vincent And The Grenadines | Bridgetown, Barbados, Barbados | Castries, St. Lucia, Saint Lucia | Falmouth Harbour, Antigua, Antigua And Barbuda | Gustavia, St. Barthelemy, St. Barthelemy | Les Saintes, Guadeloupe, Guadeloupe | Little Bay, Montserrat, Montserrat | Mayreau, Saint Vincent And$2,399
Up To $250 Onboard Credit
 
2 reviews
Itinerary Map/Ship Image
WindstarStar BreezeCaribbeanSan JuanSan Juan7 NightsBequia, Saint Vincent And The Grenadines | Les Saintes, Guadeloupe, Guadeloupe | Philipsburg, St. Maarten, Saint Maarten | Pigeon Island, St. Lucia, Saint Lucia | San Juan, Puerto Rico | St. GeorgeS, Grenada, Grenada$1,499
Up To $150 Onboard Credit
Suite!

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