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ROAD BAY, ANGUILLA cruises 75 ROAD BAY, ANGUILLA cruises

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75 cruises found

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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: Dec 28

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

$5519*
$394/night*
Oceanview
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$5519* luxurycruiseconnections.com $5467* luxuryonly.com $5467* dreamvacations.com
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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, Jan 25, Mar 01, Mar 08, Mar 22, Dec 28 More

$2467*
$352/night*
Oceanview
View Deal
$2467* luxurycruiseconnections.com $2519* luxuryonly.com $2519* dreamvacations.com
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$4167*

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$2494*

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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
 

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$3667*

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$6267*

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$3667*

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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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$6019*

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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
  • 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
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$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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$5651*

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$11519*

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$5501*

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$11451*

 

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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
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$4119*

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$9819*

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$4119*

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$9819*

 

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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
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$4319*

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$10019*

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$4319*

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$10019*

 

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$4319*

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$10019*

 

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$3819*

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$9519*

See Offers

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$3819*

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$9519*

 

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$3819*

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$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
  • 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
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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
  • 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

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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
  • 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:

$4519*
$323/night*
Oceanview
View Deal
$4519* luxurycruiseconnections.com $4519* luxuryonly.com $4519* dreamvacations.com
Loading itinerary...
Loading reviews...

Top positive review

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

N/A

$4519*

N/A

$11119*

See Offers

N/A

$4519*

N/A

$11119*

 

N/A

$4519*

N/A

$11119*

1 - 10 of 75

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