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19 cruises found

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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
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 - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$6370*
$303/night*
Oceanview
View Deal
$6370* luxurycruiseconnections.com $6546* luxuryonly.com $6546* dreamvacations.com
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Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6370*

N/A

$14970*

See Offers

N/A

$6546*

N/A

$15146*

 

N/A

$6546*

N/A

$15146*

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

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$2636*
$377/night*
Oceanview
View Deal
$2636* luxurycruiseconnections.com $2659* luxuryonly.com $2659* dreamvacations.com
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Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2636*

N/A

$5536*

See Offers

N/A

$2659*

N/A

$5559*

 

N/A

$2659*

N/A

$5559*

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
  • 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 - 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 - 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* luxuryonly.com $18146* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$18146*

N/A

$38246*

See Offers

N/A

$18146*

N/A

$38246*

 

N/A

$18146*

N/A

$38246*

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* luxuryonly.com $8646* dreamvacations.com
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Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$8495*

N/A

$19995*

See Offers

N/A

$8646*

N/A

$20146*

 

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
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 - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$4147*
$296/night*
Oceanview
View Deal
$4147* luxurycruiseconnections.com $4346* luxuryonly.com $4346* 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

$4147*

N/A

$9847*

See Offers

N/A

$4346*

N/A

$10046*

 

N/A

$4346*

N/A

$10046*

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* luxuryonly.com $4259* dreamvacations.com
Loading itinerary...
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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

$4259*

N/A

$9959*

See Offers

N/A

$4259*

N/A

$9959*

 

N/A

$4259*

N/A

$9959*

Ports

  • Ft. Lauderdale (Port Everglades), Florida
  • Port Royal
  • Oranjestad, Aruba
  • Willemstad, Curacao
  • Charlotte Amalie, St. Thomas
  • Basseterre, St. Kitts
  • St. John's, Antigua
  • Deshaies, Guadeloupe
  • Castries, St. Lucia
  • St. George's, Grenada
  • Bequia, Grenadines
  • Bridgetown, Barbados
View more ports

Ports

Ft. Lauderdale (Port Everglades), Florida - Port Royal - Oranjestad, Aruba - Willemstad, Curacao - Charlotte Amalie, St. Thomas - Basseterre, St. Kitts - St. John's, Antigua - Deshaies, Guadeloupe - Castries, St. Lucia - St. George's, Grenada - Bequia, Grenadines - Bridgetown, Barbados - View more ports

Silver Moon XL

4.4
(10 Reviews)

2024 sail dates:

$5300*
$353/night*
Suite
View Deal
$5300* luxurycruiseconnections.com $5300* luxuryonly.com $5300* gotosea.com $5300* dreamvacations.com
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Read all 10 Silver Moon reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$5300*

See Offers

N/A

N/A

N/A

$5300*

See Offers

N/A

N/A

N/A

$5300*

 

N/A

N/A

N/A

$5300*

Ports

  • Willemstad, Curacao
  • Charlotte Amalie, St. Thomas
  • Basseterre, St. Kitts
  • St. John's, Antigua
  • Deshaies, Guadeloupe
  • Castries, St. Lucia
  • Scarborough, Tobago
  • Bequia, Grenadines
  • Bridgetown, Barbados
View more ports

Ports

Willemstad, Curacao - Charlotte Amalie, St. Thomas - Basseterre, St. Kitts - St. John's, Antigua - Deshaies, Guadeloupe - Castries, St. Lucia - Scarborough, Tobago - Bequia, Grenadines - Bridgetown, Barbados - View more ports

Silver Moon XL

4.4
(10 Reviews)

2024 sail dates:

$7700*
$856/night*
Suite
View Deal
$7700* luxurycruiseconnections.com $7700* luxuryonly.com $7700* gotosea.com $7700* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$7700*

See Offers

N/A

N/A

N/A

$7700*

See Offers

N/A

N/A

N/A

$7700*

 

N/A

N/A

N/A

$7700*

Ports

  • Miami, Florida
  • ROAD BAY, ANGUILLA
  • Roseau, Dominica
  • Deshaies, Guadeloupe
  • Marigot, Saint Martin
  • San Juan, Puerto Rico
View more ports

Ports

Miami, Florida - ROAD BAY, ANGUILLA - Roseau, Dominica - Deshaies, Guadeloupe - Marigot, Saint Martin - San Juan, Puerto Rico - View more ports

Explora II M

2025 sail dates:

$3460*
$494/night*
Suite
View Deal
$3460* luxurycruiseconnections.com $3465* luxuryonly.com $3465* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$3460*

See Offers

N/A

N/A

N/A

$3465*

 

N/A

N/A

N/A

$3465*

Ports

  • Miami, Florida
  • St. John, U.S. Virgin Islands
  • Deshaies, Guadeloupe
  • Bridgetown, Barbados
View more ports

Ports

Miami, Florida - St. John, U.S. Virgin Islands - Deshaies, Guadeloupe - Bridgetown, Barbados - View more ports

Explora I M

4.5
(7 Reviews)

2025 sail dates:

$2325*
$465/night*
Suite
View Deal
$2325* luxurycruiseconnections.com $2345* luxuryonly.com $2345* dreamvacations.com
Loading itinerary...
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Read all 7 Explora I reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

N/A

N/A

$2325*

See Offers

N/A

N/A

N/A

$2345*

 

N/A

N/A

N/A

$2345*

1 - 10 of 19

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