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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
(77 Reviews)

2024 sail dates: Dec 28

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

$4599*
$329/night*
Oceanview
View Deal
$4599* luxurycruiseconnections.com $4199* luxuryonly.com $4199* cruisesonly.com $4199* cruises.com $4199* dreamvacations.com
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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
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
(77 Reviews)

2024 sail dates: Dec 28

2025 sail dates: Jan 11, Jan 25, Mar 01, Mar 08, Mar 22, Dec 14, Dec 28 More

$2399*
$343/night*
Oceanview
View Deal
$2399* luxurycruiseconnections.com $2399* luxuryonly.com $2399* cruisesonly.com $2399* cruises.com $2399* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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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
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
(77 Reviews)

2025 sail dates: Feb 01

2026 sail dates:

$2499*
$357/night*
Oceanview
View Deal
$2499* luxurycruiseconnections.com $2499* luxuryonly.com $2499* cruisesonly.com $2499* cruises.com $2499* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$2599*

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$5499*

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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
(77 Reviews)

2026 sail dates: Feb 28,

$3699*
$264/night*
Oceanview
View Deal
$3699* luxurycruiseconnections.com $3699* luxuryonly.com $3699* cruisesonly.com $3699* cruises.com $3699* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$3699*

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$9399*

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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
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, 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 - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports

Wind Surf S

4.4
(77 Reviews)

2024 sail dates: Dec 21

2025 sail dates: Jan 04, Jan 25, Feb 08, Mar 01, More

$4549*
$325/night*
Oceanview
View Deal
$4549* luxurycruiseconnections.com $4199* luxuryonly.com $4199* cruisesonly.com $4199* cruises.com $4199* dreamvacations.com
Loading itinerary...
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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
(77 Reviews)

2025 sail dates: Jan 18, Dec 21

$3699*
$264/night*
Oceanview
View Deal
$3699* luxurycruiseconnections.com $3699* luxuryonly.com $3699* cruisesonly.com $3699* cruises.com $3699* dreamvacations.com
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Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$4899*

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$10499*

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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
(77 Reviews)

2025 sail dates: Dec 14

2026 sail dates:

$3699*
$264/night*
Oceanview
View Deal
$3699* luxurycruiseconnections.com $3699* luxuryonly.com $3699* cruisesonly.com $3699* cruises.com $3699* dreamvacations.com
Loading itinerary...
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Top positive review

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Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3999*

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$9699*

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$3999*

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$9699*

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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
  • Soper's Hole, Tortola, B.V.I.
  • Jost Van Dyke, 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 - Soper's Hole, Tortola, B.V.I. - Jost Van Dyke, B.V.I. - Spanish Town, Virgin Gorda, B.V.I. - View more ports

Wind Surf S

4.4
(77 Reviews)

2025 sail dates:

$4699*
$336/night*
Oceanview
View Deal
$4699* luxurycruiseconnections.com $4399* luxuryonly.com $4399* cruisesonly.com $4399* cruises.com $4399* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$4699*

N/A

$10199*

See Offers

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$4399*

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$10199*

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$10199*

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$10199*

 

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$10199*

Ports

  • Philipsburg, St. Maarten
  • 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 - 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
(77 Reviews)

2025 sail dates:

$1999*
$400/night*
Oceanview
View Deal
$1999* luxuryonly.com $1999* cruisesonly.com $1999* cruises.com $1999* dreamvacations.com
Loading itinerary...
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Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$1999*

N/A

$4599*

See Offers

N/A

$1999*

N/A

$4599*

See Offers

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$1999*

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$4599*

 

N/A

$1999*

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$4599*

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
(77 Reviews)

2026 sail dates:

$5999*
$286/night*
Oceanview
View Deal
$5999* luxuryonly.com $5999* cruisesonly.com $5999* cruises.com $5999* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

Top critical review

Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$5999*

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$14599*

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$5999*

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$14599*

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