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windstar cruises

cruises to caribbean

Windstar Cruises to Caribbean

Showing 126-140 of 140 results

Showing 126-140 of 140 results

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Meet Natalie Thompson, one of Avoya's trusted travel advisors.

Our team has helped more than 2.5 million travelers save time, save money, and book their perfect vacation.

Choose your adventure and let us handle the rest.

Your dedicated Personal Travel Advisor is here to help you plan the vacation of your dreams. From finding the best price to answering every question, we are with you every step of the way at no extra cost.

Help Me Plan

Meet Natalie Thompson, one of Avoya's trusted travel advisors.

Our team has helped more than 2.5 million travelers save time, save money, and book their perfect vacation.

Choose your adventure and let us handle the rest.

Your dedicated Personal Travel Advisor is here to help you plan the vacation of your dreams. From finding the best price to answering every question, we are with you every step of the way at no extra cost.

Help Me Plan

14-night caribbean cruise

$4,893

Windstar Cruises – Star Legend

4.5 (86)

5 Star

73%

4 Star

9%

3 Star

10%

2 Star

3%

1 Star

3%

Date:

Feb 14, 2028 View Other Dates

Ports:

San Juan → Saint John → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Basse Terre) → Jost Van Dyke → Virgin Gorda → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

San Juan → Saint John → Saint Maarten (Phillipsburg) → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Basse Terre) → Jost Van Dyke → Virgin Gorda → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Feb 14, 2028 from San Juan, Puerto Rico

Oceanview From

$4,893

Top Picks Rank:

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Feb 20, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Philipsburg

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Philipsburg

Departs Feb 20, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$3,051

Top Picks Rank:

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Feb 20, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Falmouth Harbour → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Philipsburg

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Falmouth Harbour → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Philipsburg

Departs Feb 20, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$4,819

Top Picks Rank:

7-night caribbean cruise

$3,030

Windstar Cruises – Star Legend

4.5 (86)

5 Star

73%

4 Star

9%

3 Star

10%

2 Star

3%

1 Star

3%

Date:

Feb 21, 2028 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Feb 21, 2028 from San Juan, Puerto Rico

Oceanview From

$3,030

Top Picks Rank:

7-night caribbean cruise

$2,967

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Feb 27, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → Falmouth Harbour → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Philipsburg

Saint Maarten (Phillipsburg) → Falmouth Harbour → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Philipsburg

Departs Feb 27, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$2,967

Top Picks Rank:

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Feb 27, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → Falmouth Harbour → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Philipsburg

Saint Maarten (Phillipsburg) → Falmouth Harbour → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Philipsburg

Departs Feb 27, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$4,819

Top Picks Rank:

7-night caribbean cruise

$3,365

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Feb 28, 2028

Ports:

Balboa → Panama Canal → Bocas Del Toro → San Blas Island → Cartagena → Oranjestad

Departs Feb 28, 2028 from Balboa, Panama

Oceanview From

$3,365

Top Picks Rank:

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 05, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Philipsburg

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Philipsburg

Departs Mar 05, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$3,051

Top Picks Rank:

14-night caribbean cruise

$4,819

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 05, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Philipsburg

Saint Maarten (Phillipsburg) → Saint Kitts And Nevis (Charlestown) → Roseau → Mayreau Island → Isle De Saintes → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → San Jose → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Philipsburg

Departs Mar 05, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$4,819

Top Picks Rank:

7-night caribbean cruise

$2,967

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 12, 2028 View Other Dates

Ports:

Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Philipsburg

Saint Maarten (Phillipsburg) → San Jose → Road Bay → Jost Van Dyke → Sopers Hole → Virgin Gorda → Saint Barthelemy (Gustavia) → Philipsburg

Departs Mar 12, 2028 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$2,967

Top Picks Rank:

7-night caribbean cruise

$3,030

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 13, 2028 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Mar 13, 2028 from San Juan, Puerto Rico

Oceanview From

$3,030

Top Picks Rank:

14-night caribbean cruise

$4,893

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 13, 2028 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

Departs Mar 13, 2028 from San Juan, Puerto Rico

Oceanview From

$4,893

Top Picks Rank:

7-night caribbean cruise

$3,062

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 20, 2028 View Other Dates

Ports:

San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → San Juan

Departs Mar 20, 2028 from San Juan, Puerto Rico

Oceanview From

$3,062

Top Picks Rank:

14-night caribbean cruise

$4,893

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 20, 2028 View Other Dates

Ports:

San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

San Juan → Saint John → Saint Kitts And Nevis (Basse Terre) → Saint Barthelemy (Gustavia) → Saint Maarten (Phillipsburg) → Jost Van Dyke → Virgin Gorda → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Mar 20, 2028 from San Juan, Puerto Rico

Oceanview From

$4,893

Top Picks Rank:

7-night caribbean cruise

$3,030

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

7%

2 Star

1%

1 Star

1%

Date:

Mar 27, 2028 View Other Dates

Ports:

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

San Juan → Saint George's → Saint Vincent And Grenadines (Bequia) → Mayreau Island → Isle De Saintes → Saint Martin (Marigot) → San Juan

Departs Mar 27, 2028 from San Juan, Puerto Rico

Oceanview From

$3,030

Top Picks Rank:

Showing 25 of 140 results

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