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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

$5119*
$366/night*
Oceanview
View Deal
$5119* 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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$6867*

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$11119*

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$11467*

 

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$11019*

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$5467*

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$10967*

 

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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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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$4667*

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$4167*

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$2494*

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Ports

  • Venice, Italy
  • Rovinj, Croatia
  • Split, Croatia
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Giardini Di Naxos (Taormina), Sicily
  • Sorrento, Italy
  • Civitavecchia (Rome), Italy
  • Portoferraio, Elba
  • Portofino, Italy
  • Monte Carlo, Monaco
  • Cannes, France
  • Sanary-Sur-Mer, France
  • Palamos, Spain
  • Barcelona, Spain
View more ports

Ports

Venice, Italy - Rovinj, Croatia - Split, Croatia - Dubrovnik, Croatia - Kotor, Montenegro - Giardini Di Naxos (Taormina), Sicily - Sorrento, Italy - Civitavecchia (Rome), Italy - Portoferraio, Elba - Portofino, Italy - Monte Carlo, Monaco - Cannes, France - Sanary-Sur-Mer, France - Palamos, Spain - Barcelona, Spain - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: May 05,

$5494*
$366/night*
Oceanview
View Deal
$5494* luxurycruiseconnections.com $5447* luxuryonly.com $5447* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$7690*

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$7690*

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$5494*

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$8244*

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$5447*

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$8197*

 

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$5447*

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$8197*

Ports

  • Civitavecchia (Rome), Italy
  • Amalfi, Italy
  • VIBO VALENTIA, ITALY
  • REGGIO CALABRIA, ITALY
  • Taranto
  • Otranto, Italy
  • Rab Island, Croatia
  • Venice, Italy
  • Rovinj, Croatia
  • Zadar, Croatia
  • Hvar, Croatia
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Piran, Slovenia
View more ports

Ports

Civitavecchia (Rome), Italy - Amalfi, Italy - VIBO VALENTIA, ITALY - REGGIO CALABRIA, ITALY - Taranto - Otranto, Italy - Rab Island, Croatia - Venice, Italy - Rovinj, Croatia - Zadar, Croatia - Hvar, Croatia - Dubrovnik, Croatia - Kotor, Montenegro - Piran, Slovenia - View more ports

Wind Surf S

4.4
(78 Reviews)

2026 sail dates: Aug 01

$5806*
$342/night*
Oceanview
View Deal
$5806* luxurycruiseconnections.com $5737* luxuryonly.com $5737* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$5806*

N/A

$9746*

See Offers

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$5737*

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$9677*

 

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$5737*

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$9677*

 

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$5806*

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$9746*

See Offers

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$5737*

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$9677*

 

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$5737*

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$9677*

Ports

  • Civitavecchia (Rome), Italy
  • Sorrento, Italy
  • Giardini Di Naxos (Taormina), Sicily
  • Kotor, Montenegro
  • Dubrovnik, Croatia
  • Split, Croatia
  • Rovinj, Croatia
  • Venice, Italy
View more ports

Ports

Civitavecchia (Rome), Italy - Sorrento, Italy - Giardini Di Naxos (Taormina), Sicily - Kotor, Montenegro - Dubrovnik, Croatia - Split, Croatia - Rovinj, Croatia - Venice, Italy - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Apr 27, Jun 06, Aug 19, More

2026 sail dates: Sep 02

$8047*
$1006/night*
Oceanview
View Deal
$8047* luxurycruiseconnections.com $4147* luxuryonly.com $4147* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

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$4647*

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$7127*

See Offers

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$4747*

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$7227*

 

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$6547*

 

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$4547*

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$6547*

 

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$4547*

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$6547*

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

$2866*

N/A

$6267*

See Offers

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$2946*

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$7567*

 

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$2946*

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$7567*

 

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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

  • Venice, Italy
  • Rovinj, Croatia
  • Split, Croatia
  • Dubrovnik, Croatia
  • Kotor, Montenegro
  • Giardini Di Naxos (Taormina), Sicily
  • Sorrento, Italy
  • Civitavecchia (Rome), Italy
View more ports

Ports

Venice, Italy - Rovinj, Croatia - Split, Croatia - Dubrovnik, Croatia - Kotor, Montenegro - Giardini Di Naxos (Taormina), Sicily - Sorrento, Italy - Civitavecchia (Rome), Italy - View more ports

Wind Surf S

4.4
(78 Reviews)

2025 sail dates: Sep 14, Oct 10, Oct 26,

2026 sail dates: May 13, Aug 18

$4047*
$506/night*
Oceanview
View Deal
$4047* luxurycruiseconnections.com $4085* luxuryonly.com $4085* dreamvacations.com
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Read all 78 Wind Surf reviews
Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6947*

N/A

$10187*

See Offers

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$5247*

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$8487*

 

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$5247*

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$8487*

 

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$4147*

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$6787*

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$4147*

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$6787*

 

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$4147*

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$6787*

 

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$5847*

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$7367*

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$4047*

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$5567*

 

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$4047*

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$5567*

 

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$4047*

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$6047*

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$4080*

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$6080*

 

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$4080*

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$6080*

 

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$4047*

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$4085*

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$6085*

 

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$4085*

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$6085*

 

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$4247*

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$6247*

See Offers

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$4287*

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$6287*

 

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$4287*

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$6287*

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:

2025 sail dates: Jan 18, Feb 22

$2610*
$373/night*
Oceanview
View Deal
$2610* luxurycruiseconnections.com $2450* luxuryonly.com $2450* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$2610*

N/A

$6151*

See Offers

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$2450*

N/A

$6151*

 

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$2450*

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$6151*

 

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$3451*

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$6251*

See Offers

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$3519*

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$6319*

 

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$3519*

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$6319*

 

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$3451*

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$6251*

See Offers

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$3519*

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$6319*

 

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$3519*

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$6319*

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: Feb 08, Mar 15,

$4439*
$317/night*
Oceanview
View Deal
$4439* luxurycruiseconnections.com $6851* luxuryonly.com $6851* dreamvacations.com
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Partners Bonus Offers Inside Oceanview Balcony Suite
 

N/A

$6769*

N/A

N/A

 

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$4439*

N/A

$11169*

See Offers

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$6851*

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$6851*

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N/A

 

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$5609*

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$11119*

See Offers

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$5541*

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$11051*

 

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$5541*

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$11051*

 

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$5219*

N/A

$11519*

See Offers

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$5151*

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$11051*

 

N/A

$5151*

N/A

$11051*

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
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

$6019*

N/A

$11419*

See Offers

N/A

$6019*

N/A

$11419*

 

N/A

$6019*

N/A

$11419*

 

N/A

$3819*

N/A

$9519*

See Offers

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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*

N/A

$10119*

See Offers

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$4419*

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$10119*

 

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$4419*

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$10119*

1 - 10 of 396

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

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