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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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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, Jan 25, Mar 01, Mar 08, Mar 22, Dec 14, Dec 28 More

$2467*
$352/night*
Oceanview
View Deal
$2467* luxurycruiseconnections.com $2494* luxuryonly.com $2494* dreamvacations.com
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Ports

  • Miami, Florida
  • St. John's, Antigua
  • Castries, St. Lucia
  • St. George's, Grenada
  • Bridgetown, Barbados
  • Roseau, Dominica
  • Gustavia, St. Barthelemy
View more ports

Ports

Miami, Florida - St. John's, Antigua - Castries, St. Lucia - St. George's, Grenada - Bridgetown, Barbados - Roseau, Dominica - Gustavia, St. Barthelemy - View more ports

Vista M

4.3
(42 Reviews)

2025 sail dates: Feb 19, Mar 09,

$3080*
$280/night*
Balcony
View Deal
$3080* luxurycruiseconnections.com $4399* avoyatravel.com $4849* luxuryonly.com $4849* dreamvacations.com $3080* directlinecruises.com $3080* americandiscountcruises.com $3080* gotosea.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
  • 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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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$3667*

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$6267*

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$3667*

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$6267*

 

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$6267*

 

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$2610*

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$5510*

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$2846*

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$5746*

 

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$2846*

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$5746*

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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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$6019*

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$11419*

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$11419*

 

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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
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)

2024 sail dates: Dec 21

2025 sail dates: Jan 18,

$2771*
$396/night*
Oceanview
View Deal
$2771* luxurycruiseconnections.com $2839* luxuryonly.com $2839* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$3951*

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$6151*

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$3351*

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$6251*

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$2839*

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$6319*

 

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$6319*

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

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$4119*

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$9819*

See Offers

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$4119*

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$9819*

 

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$4119*

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$9519*

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$3819*

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$9519*

 

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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
  • 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)

2024 sail dates: Dec 21

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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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$7519*

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$5719*

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$11451*

 

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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
(78 Reviews)

2026 sail dates: Feb 28,

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

$4319*

N/A

$10019*

See Offers

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$4319*

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$10019*

 

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$4319*

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$10019*

 

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$9519*

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$9519*

Ports

  • Miami, Florida
  • St. John's, Antigua
  • Castries, St. Lucia
  • St. George's, Grenada
  • Bridgetown, Barbados
  • Roseau, Dominica
  • Gustavia, St. Barthelemy
  • Great Stirrup Cay (Cruise Line Private Island), Bahamas
  • Royal Naval Dockyard, West End, Bermuda
  • Charleston, South Carolina
  • FERNANDINA BEACH, FL
  • Port Canaveral, Florida
  • Nassau, Bahamas
View more ports

Ports

Miami, Florida - St. John's, Antigua - Castries, St. Lucia - St. George's, Grenada - Bridgetown, Barbados - Roseau, Dominica - Gustavia, St. Barthelemy - Great Stirrup Cay (Cruise Line Private Island), Bahamas - Royal Naval Dockyard, West End, Bermuda - Charleston, South Carolina - FERNANDINA BEACH, FL - Port Canaveral, Florida - Nassau, Bahamas - View more ports

Vista M

4.3
(42 Reviews)

2025 sail dates:

$9199*
$400/night*
Balcony
View Deal
$9199* luxurycruiseconnections.com $9199* avoyatravel.com $9199* luxuryonly.com $9199* dreamvacations.com $9199* directlinecruises.com $9199* americandiscountcruises.com $9199* gotosea.com
Loading itinerary...
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Read all 42 Vista reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

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N/A

$9199*

$13399*

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$9199*

$13399*

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$13399*

 

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