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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
  • 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
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Partners Bonus Offers Inside Oceanview Balcony Suite
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$5999*

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$14599*

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$5999*

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$14599*

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$5999*

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$14599*

 

N/A

$5999*

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$14599*

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
  • 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 - 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 - 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
(77 Reviews)

2026 sail dates:

$16599*
$302/night*
Oceanview
View Deal
$16599* luxurycruiseconnections.com $16599* luxuryonly.com $16599* cruisesonly.com $16599* cruises.com $16599* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$16599*

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$36699*

See Offers

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$16599*

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$36699*

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$16599*

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$36699*

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$16599*

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$36699*

 

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$16599*

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$36699*

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
(77 Reviews)

2026 sail dates:

$2499*
$357/night*
Oceanview
View Deal
$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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N/A

$2499*

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$5399*

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$2499*

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$5399*

See Offers

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$2499*

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$5399*

 

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$2499*

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$5399*

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
(77 Reviews)

2026 sail dates:

$3799*
$271/night*
Oceanview
View Deal
$3799* luxuryonly.com $3799* cruisesonly.com $3799* cruises.com $3799* dreamvacations.com
Loading itinerary...
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Read all 77 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
See Offers

N/A

$3799*

N/A

$9499*

See Offers

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$3799*

N/A

$9499*

See Offers

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$3799*

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$9499*

 

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$3799*

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$9499*

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
(77 Reviews)

2026 sail dates:

$7899*
$282/night*
Oceanview
View Deal
$7899* luxurycruiseconnections.com $7899* luxuryonly.com $7899* cruisesonly.com $7899* cruises.com $7899* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$7899*

N/A

$19399*

See Offers

N/A

$7899*

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$19399*

See Offers

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$7899*

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$19399*

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$7899*

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$19399*

 

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$7899*

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$19399*

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
(77 Reviews)

2026 sail dates:

$3999*
$286/night*
Oceanview
View Deal
$3999* luxuryonly.com $3999* cruisesonly.com $3999* cruises.com $3999* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
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N/A

$3999*

N/A

$9699*

See Offers

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$3999*

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$9699*

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$3999*

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$9699*

 

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$3999*

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$9699*

Ports

  • Bridgetown, Barbados
  • Castries, St. Lucia
  • Deshaies, Guadeloupe
  • St. John's, Antigua
  • Philipsburg, St. Maarten
  • Jost Van Dyke, B.V.I.
  • San Juan, Puerto Rico
  • Miami, Florida
View more ports

Ports

Bridgetown, Barbados - Castries, St. Lucia - Deshaies, Guadeloupe - St. John's, Antigua - Philipsburg, St. Maarten - Jost Van Dyke, B.V.I. - San Juan, Puerto Rico - Miami, Florida - View more ports

Crystal Serenity XL

4.4
(104 Reviews)

2024 sail dates:

$4300*
$478/night*
Oceanview
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$4300* luxurycruiseconnections.com $4300* americandiscountvacations.com $4300* americandiscountcruises.com $4300* gotosea.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$4300*

$4500*

$5300*

See Offers

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$4300*

$4500*

$5300*

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$4300*

$4500*

$5300*

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$4300*

$4500*

$5300*

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
(9 Reviews)

2024 sail dates:

$7300*
$487/night*
Suite
View Deal
$7300* avoyatravel.com $7300* luxurycruiseconnections.com $7300* luxuryonly.com $7300* cruisesonly.com $7300* cruises.com $7300* dreamvacations.com $7300* americandiscountvacations.com $7300* americandiscountcruises.com $7300* gotosea.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
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$7300*

 

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$7300*

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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
(9 Reviews)

2024 sail dates:

$5100*
$567/night*
Suite
View Deal
$5100* avoyatravel.com $10100* luxurycruiseconnections.com $10100* luxuryonly.com $10100* cruisesonly.com $10100* cruises.com $10100* dreamvacations.com $10100* americandiscountvacations.com $10100* americandiscountcruises.com $10100* gotosea.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
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$5100*

 

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$10100*

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$10100*

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:

$3375*
$482/night*
Suite
View Deal
$3375* luxurycruiseconnections.com $4275* luxuryonly.com $4275* cruisesonly.com $4275* cruises.com $4275* dreamvacations.com $3375* americandiscountvacations.com $3375* americandiscountcruises.com
Loading itinerary...
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Top positive review

Top critical review

Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$3375*

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$4275*

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1 - 10 of 10

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