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20 cruises found

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Ports

  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
  • Anse Mitan, Martinique
View more ports

Ports

Philipsburg, St. Maarten - Basseterre, St. Kitts - Gustavia, St. Barthelemy - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Pigeon Island, St. Lucia - Bridgetown, Barbados - Anse Mitan, Martinique - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$4037*
$288/night*
Oceanview
View Deal
$4037* luxurycruiseconnections.com $4037* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4037*

N/A

$10437*

 

N/A

$4037*

N/A

$10437*

Ports

  • Bridgetown, Barbados
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Anse Mitan, Martinique
  • Pigeon Island, St. Lucia
  • Castries, St. Lucia
  • Kingstown, St. Vincent
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Bequia, Grenadines
View more ports

Ports

Bridgetown, Barbados - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - Castries, St. Lucia - Kingstown, St. Vincent - Mayreau, Grenadines - St. George's, Grenada - Bequia, Grenadines - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$4133*
$295/night*
Oceanview
View Deal
$4133* luxurycruiseconnections.com $4133* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4133*

N/A

$10033*

 

N/A

$4133*

N/A

$10033*

Ports

  • Bridgetown, Barbados
  • Little Bay, Montserrat
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Anse Mitan, Martinique
  • Pigeon Island, St. Lucia
View more ports

Ports

Bridgetown, Barbados - Little Bay, Montserrat - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates: Mar 07,

$2616*
$374/night*
Oceanview
View Deal
$2616* luxurycruiseconnections.com $2642* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2716*

N/A

$5716*

 

N/A

$2733*

N/A

$5733*

 

N/A

$2616*

N/A

$5616*

 

N/A

$2642*

N/A

$5642*

Ports

  • Bridgetown, Barbados
  • Basseterre, St. Kitts
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Roseau, Dominica
  • Anse Mitan, Martinique
  • Pigeon Island, St. Lucia
  • Lisbon, Portugal
View more ports

Ports

Bridgetown, Barbados - Basseterre, St. Kitts - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Roseau, Dominica - Anse Mitan, Martinique - Pigeon Island, St. Lucia - Lisbon, Portugal - View more ports

Wind Spirit S

4.5
(20 Reviews)

2026 sail dates:

$4142*
$188/night*
Oceanview
View Deal
$4142* luxurycruiseconnections.com $4142* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4142*

N/A

$9642*

 

N/A

$4142*

N/A

$9642*

Ports

  • Philipsburg, St. Maarten
  • Basseterre, St. Kitts
  • Little Bay, Montserrat
  • Gustavia, St. Barthelemy
  • Deshaies, Guadeloupe
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Bridgetown, Barbados
  • Anse Mitan, Martinique
  • Castries, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • St. George's, Grenada
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 - Anse Mitan, Martinique - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$4259*
$304/night*
Oceanview
View Deal
$4259* luxurycruiseconnections.com $4259* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4259*

N/A

$9959*

 

N/A

$4259*

N/A

$9959*

Ports

  • Bridgetown, Barbados
  • Anse Mitan, Martinique
  • Pigeon Island, St. Lucia
  • Castries, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • St. George's, Grenada
View more ports

Ports

Bridgetown, Barbados - Anse Mitan, Martinique - Pigeon Island, St. Lucia - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$2722*
$389/night*
Oceanview
View Deal
$2722* luxurycruiseconnections.com $2747* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2722*

N/A

$5622*

 

N/A

$2747*

N/A

$5647*

Ports

  • Bridgetown, Barbados
  • Anse Mitan, Martinique
  • Castries, St. Lucia
  • Pigeon Island, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Charlotteville, Tobago
  • Soufriere, St. Lucia
  • Kralendijk, Bonaire
  • Willemstad, Curacao
  • Oranjestad, Aruba
View more ports

Ports

Bridgetown, Barbados - Anse Mitan, Martinique - Castries, St. Lucia - Pigeon Island, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - Charlotteville, Tobago - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$4647*
$332/night*
Oceanview
View Deal
$4647* luxurycruiseconnections.com $4647* dreamvacations.com
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Top positive review

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Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4647*

N/A

$10347*

 

N/A

$4647*

N/A

$10347*

Ports

  • Philipsburg, St. Maarten
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, 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 Mitan, Martinique
  • Castries, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • St. George's, Grenada
  • Charlotteville, Tobago
  • Soufriere, St. Lucia
  • Kralendijk, Bonaire
  • Willemstad, Curacao
  • Oranjestad, Aruba
View more ports

Ports

Philipsburg, St. Maarten - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, 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 Mitan, Martinique - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - Charlotteville, Tobago - Soufriere, St. Lucia - Kralendijk, Bonaire - Willemstad, Curacao - Oranjestad, Aruba - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$8495*
$303/night*
Oceanview
View Deal
$8495* luxurycruiseconnections.com $8646* dreamvacations.com
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Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$8495*

N/A

$19995*

 

N/A

$8646*

N/A

$20146*

Ports

  • Philipsburg, St. Maarten
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • 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 Mitan, 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
  • Colon, Panama
  • San Andres Island (Isla San Andres), Colombia
  • Coxen Hole, Roatan, Bay Islands, Honduras
  • Belize City, Belize
  • Costa Maya (Mahahual), Mexico
  • Cozumel, Mexico
  • George Town, Grand Cayman
  • Cayman Brac
  • Port Antonio, Jamaica
  • Santo Domingo, Dominican Republic
  • La Romana, Dominican Republic
View more ports

Ports

Philipsburg, St. Maarten - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - 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 Mitan, 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 - Colon, Panama - San Andres Island (Isla San Andres), Colombia - Coxen Hole, Roatan, Bay Islands, Honduras - Belize City, Belize - Costa Maya (Mahahual), Mexico - Cozumel, Mexico - George Town, Grand Cayman - Cayman Brac - Port Antonio, Jamaica - Santo Domingo, Dominican Republic - La Romana, Dominican Republic - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$18146*
$330/night*
Oceanview
View Deal
$18146* luxurycruiseconnections.com $18146* dreamvacations.com
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Top positive review

Top critical review

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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$18146*

N/A

$38246*

 

N/A

$18146*

N/A

$38246*

Ports

  • Philipsburg, St. Maarten
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • 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 Mitan, Martinique
  • Castries, St. Lucia
  • Bequia, Grenadines
  • Mayreau, Grenadines
  • St. George's, Grenada
View more ports

Ports

Philipsburg, St. Maarten - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - 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 Mitan, Martinique - Castries, St. Lucia - Bequia, Grenadines - Mayreau, Grenadines - St. George's, Grenada - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$6370*
$303/night*
Oceanview
View Deal
$6370* luxurycruiseconnections.com $6546* dreamvacations.com
Loading itinerary...
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Top positive review

Top critical review

Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6370*

N/A

$14970*

 

N/A

$6546*

N/A

$15146*

11 - 20 of 20

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