Windstar Cruises Cruises to Caribbean - Southern 28 Cruises on Windstar Cruises Found

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Ports

  • Miami, Florida
  • Key West, Florida
  • Cozumel, Mexico
  • Belize City, Belize
  • Trujillo, Honduras
  • San Antonio, Chile
  • Puerto Limon, Costa Rica
  • Bocas Del Toro, Panama
  • Colon, Panama
View More Ports

Ports

Miami, Florida - Key West, Florida - Cozumel, Mexico - Belize City, Belize - Trujillo, Honduras - San Antonio, Chile - Puerto Limon, Costa Rica - Bocas Del Toro, Panama - Colon, Panama - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$2699*

 

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$2699*

 

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$2599*

$3499*

$5299*

Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Bequia, Grenadines
  • St. George's, Grenada
  • Pigeon Island, St. Lucia
  • VIEQUES, PUERTO RICO
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View More Ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Bequia, Grenadines - St. George's, Grenada - Pigeon Island, St. Lucia - VIEQUES, PUERTO RICO - Gustavia, St. Barthelemy - Little Bay, Montserrat - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3699*

$5699*

$8199*

 

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$3699*

$5699*

$8199*

 

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$3699*

$5699*

$8199*

 

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$3699*

$5699*

$8199*

Ports

  • Philipsburg, St. Maarten
  • Barbuda, Barbuda
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
View More Ports

Ports

Philipsburg, St. Maarten - Barbuda, Barbuda - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$1599*

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$1599*

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$1599*

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$3199*

 

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$2599*

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$2599*

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$2599*

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$4499*

 

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$2199*

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$2199*

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$4099*

Ports

  • Philipsburg, St. Maarten
  • Barbuda, Barbuda
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Falmouth Harbour,Antigua
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View More Ports

Ports

Philipsburg, St. Maarten - Barbuda, Barbuda - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Falmouth Harbour,Antigua - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3499*

N/A

$6299*

 

N/A

$3499*

N/A

$6299*

 

N/A

$3499*

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$6299*

 

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$3499*

N/A

$6299*

Ports

  • Philipsburg, St. Maarten
  • Gustavia, St. Barthelemy
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Falmouth Harbour,Antigua
View More Ports

Ports

Philipsburg, St. Maarten - Gustavia, St. Barthelemy - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Falmouth Harbour,Antigua - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$2499*

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$2499*

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$2499*

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$4699*

 

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$1999*

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$1999*

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$3899*

 

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$4099*

Ports

  • San Juan, Puerto Rico
  • VIEQUES, PUERTO RICO
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View More Ports

Ports

San Juan, Puerto Rico - VIEQUES, PUERTO RICO - Gustavia, St. Barthelemy - Little Bay, Montserrat - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$1799*

 

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$1799*

 

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$1599*

$2599*

$4699*

 

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$2899*

 

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$2699*

$3599*

$5799*

 

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$2199*

 

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$1999*

$2899*

$5099*

 

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$2399*

 

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$2399*

 

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$2199*

$2999*

$5299*

Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Bequia, Grenadines
  • Pigeon Island, St. Lucia
  • St. George's, Grenada
View More Ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Bequia, Grenadines - Pigeon Island, St. Lucia - St. George's, Grenada - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$1799*

 

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$1799*

 

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$1599*

$2399*

$4699*

 

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$1599*

 

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$1499*

$2199*

$4699*

 

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$2399*

$4699*

 

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$2699*

$3599*

$5799*

 

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$2399*

 

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$2399*

 

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$2199*

$3099*

$5299*

 

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$2399*

 

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$2399*

 

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$2199*

$3099*

$5299*

Ports

  • San Juan, Puerto Rico
  • Philipsburg, St. Maarten
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Bequia, Grenadines
  • St. George's, Grenada
  • Pigeon Island, St. Lucia
  • VIEQUES, PUERTO RICO
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
View More Ports

Ports

San Juan, Puerto Rico - Philipsburg, St. Maarten - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Bequia, Grenadines - St. George's, Grenada - Pigeon Island, St. Lucia - VIEQUES, PUERTO RICO - Gustavia, St. Barthelemy - Little Bay, Montserrat - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2374*

$3599*

$5899*

 

N/A

$3799*

$4999*

$7299*

 

N/A

$3499*

$4699*

$6999*

Ports

  • Philipsburg, St. Maarten
  • Falmouth Harbour,Antigua
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
  • Little Bay, Montserrat
  • Deshaies, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
  • ANSE MATIN, MARTINIQUE
  • Castries, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Charlotteville, Tobago
  • Soufriere, St. Lucia
  • Kralendijk, Bonaire
  • Willemstad, Curacao
  • Oranjestad, Aruba
  • Santa Marta, Colombia
  • Cartagena, Colombia
  • Bocas Del Toro, Panama
  • Puerto Limon, Costa Rica
  • Cruise Gatun Lake (Inside Panama Canal)
  • Colon, Panama
  • San Antonio, Chile
  • Coxen Hole, Roatan, Bay Islands, Honduras
  • Belize City, Belize
  • Costa Maya (Mahahual), Mexico
  • Cozumel, Mexico
  • ISLA MUJERES, MEXICO
  • George Town, Grand Cayman
  • Cayman Brac
  • Port Antonio, Jamaica
  • Santo Domingo, Dominican Republic
View More Ports

Ports

Philipsburg, St. Maarten - Falmouth Harbour,Antigua - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Little Bay, Montserrat - Deshaies, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - ANSE MATIN, MARTINIQUE - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - Charlotteville, Tobago - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - Santa Marta, Colombia - Cartagena, Colombia - Bocas Del Toro, Panama - Puerto Limon, Costa Rica - Cruise Gatun Lake (Inside Panama Canal) - Colon, Panama - San Antonio, Chile - Coxen Hole, Roatan, Bay Islands, Honduras - Belize City, Belize - Costa Maya (Mahahual), Mexico - Cozumel, Mexico - ISLA MUJERES, MEXICO - George Town, Grand Cayman - Cayman Brac - Port Antonio, Jamaica - Santo Domingo, Dominican Republic - View More Ports

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Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$12999*

N/A

$22099*

Ports

  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Little Bay, Montserrat
  • Gustavia, St. Barthelemy
  • Deshaies, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
View More Ports

Ports

Philipsburg, St. Maarten - Basseterre, St. Kitts - Little Bay, Montserrat - Gustavia, St. Barthelemy - Deshaies, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - View More Ports

Loading itinerary...
Loading reviews...

Top Positive Review

Top Critical Review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$1999*

N/A

N/A

 

N/A

$1999*

N/A

N/A

 

N/A

$1999*

N/A

$3899*

All prices are per person based on double occupancy and do not include port / government fees and gratuities.