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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
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
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 - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - View more ports

Wind Surf S

4.4
(78 Reviews)

2024 sail dates:

2025 sail dates: Jan 11, Feb 01, Feb 15, More

$5519*
$394/night*
Oceanview
View Deal
$5519* luxurycruiseconnections.com $5467* luxuryonly.com $5467* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$5719*

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$6919*

 

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$5667*

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$6819*

 

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$5467*

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$10967*

 

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$5467*

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$10967*

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
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 - View more ports

Wind Surf S

4.4
(78 Reviews)

2024 sail dates: Dec 28

2025 sail dates: Jan 11, Mar 01, Mar 08, Mar 22, Dec 14, Dec 28 More

$2447*
$350/night*
Oceanview
View Deal
$2447* luxurycruiseconnections.com $2447* luxuryonly.com $2447* dreamvacations.com
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Top critical review

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

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$4167*

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$5067*

 

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$4167*

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$2626*

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$6267*

 

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$2481*

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$4167*

 

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$3367*

 

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$2519*

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$5419*

 

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$2767*

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$5767*

 

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$3367*

 

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$5419*

 

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$3367*

 

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$2494*

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$5394*

 

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$5394*

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Feb 22

$2291*
$327/night*
Oceanview
View Deal
$2291* luxurycruiseconnections.com $2359* luxuryonly.com $2359* 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

$2291*

N/A

$4151*

 

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$2359*

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$6319*

 

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$2359*

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$6319*

 

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$2611*

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$4151*

 

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$3619*

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$6319*

 

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$3619*

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$6319*

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
  • 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.
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - 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. - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Jan 18, Dec 21

$3819*
$273/night*
Oceanview
View Deal
$3819* luxurycruiseconnections.com $3819* luxuryonly.com $3819* 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
 

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$6019*

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$7219*

 

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$6019*

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$11419*

 

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$6019*

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$11419*

 

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$3819*

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$5519*

 

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$3819*

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$9519*

 

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$3819*

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$9519*

 

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$4419*

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$6119*

 

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$4419*

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$10119*

 

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$4419*

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$10119*

Ports

  • Philipsburg, St. Maarten
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
  • Gustavia, St. Barthelemy
  • 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.
View more ports

Ports

Philipsburg, St. Maarten - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - Gustavia, St. Barthelemy - 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. - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Jan 04, Feb 08,

$5569*
$398/night*
Oceanview
View Deal
$5569* luxurycruiseconnections.com $5501* luxuryonly.com $5501* 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

$5719*

N/A

$6919*

 

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$5651*

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$5651*

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$5609*

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$6969*

 

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$5541*

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$5569*

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$6919*

 

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$5501*

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$11451*

 

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$5501*

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$11451*

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
  • Charlestown, Nevis
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Basseterre, St. Kitts
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 - Charlestown, Nevis - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Basseterre, St. Kitts - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Dec 14

2026 sail dates:

$3819*
$273/night*
Oceanview
View Deal
$3819* luxurycruiseconnections.com $3819* luxuryonly.com $3819* 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

$4119*

N/A

$5819*

 

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$4119*

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$9819*

 

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$4119*

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$9819*

 

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$3819*

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$5519*

 

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$3819*

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$9519*

 

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$3819*

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$9519*

Ports

  • Philipsburg, St. Maarten
  • Roseau, Dominica
  • Pigeon Island, St. Lucia
  • Terre-De-Haut, Iles Des Saintes, Guadeloupe
  • Gustavia, St. Barthelemy
  • Basseterre, St. Kitts
  • Falmouth Harbour,Antigua
  • ROAD BAY, ANGUILLA
  • Jost Van Dyke, B.V.I.
  • Soper's Hole, Tortola, B.V.I.
View more ports

Ports

Philipsburg, St. Maarten - Roseau, Dominica - Pigeon Island, St. Lucia - Terre-De-Haut, Iles Des Saintes, Guadeloupe - Gustavia, St. Barthelemy - Basseterre, St. Kitts - Falmouth Harbour,Antigua - ROAD BAY, ANGUILLA - Jost Van Dyke, B.V.I. - Soper's Hole, Tortola, B.V.I. - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates: Feb 28,

$3819*
$273/night*
Oceanview
View Deal
$3819* luxurycruiseconnections.com $3819* luxuryonly.com $3819* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

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

N/A

$4319*

N/A

$6019*

 

N/A

$4319*

N/A

$10019*

 

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$4319*

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$10019*

 

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$3819*

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$5519*

 

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$3819*

N/A

$9519*

 

N/A

$3819*

N/A

$9519*

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
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 - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Feb 01

2026 sail dates:

$2610*
$373/night*
Oceanview
View Deal
$2610* luxurycruiseconnections.com $2846* luxuryonly.com $2846* dreamvacations.com
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Top critical review

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

N/A

$2946*

N/A

$3426*

 

N/A

$2946*

N/A

$6267*

 

N/A

$2946*

N/A

$6267*

 

N/A

$2610*

N/A

$3510*

 

N/A

$2846*

N/A

$5746*

 

N/A

$2846*

N/A

$5746*

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* luxuryonly.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

$8970*

 

N/A

$6546*

N/A

$15146*

 

N/A

$6546*

N/A

$15146*

Ports

  • Cozumel, Mexico
  • George Town, Grand Cayman
  • Cayman Brac
  • Port Antonio, Jamaica
  • Santo Domingo, Dominican Republic
  • La Romana, Dominican Republic
  • Jost Van Dyke, B.V.I.
  • Spanish Town, Virgin Gorda, B.V.I.
  • Philipsburg, St. Maarten
View more ports

Ports

Cozumel, Mexico - George Town, Grand Cayman - Cayman Brac - Port Antonio, Jamaica - Santo Domingo, Dominican Republic - La Romana, Dominican Republic - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - Philipsburg, St. Maarten - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates:

$4063*
$369/night*
Oceanview
View Deal
$4063* luxurycruiseconnections.com $4115* luxuryonly.com $4115* 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

$4063*

N/A

$5063*

 

N/A

$4115*

N/A

$7315*

 

N/A

$4115*

N/A

$7315*

1 - 10 of 69

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

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