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cruises to caribbean

Windstar Cruises to Caribbean

Name: 21-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 7995 USD
Availability: InStock
Rating: 4.52 (95 reviews)

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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.

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21-night caribbean cruise

$7,995

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

2 Star

1 Star

Date:

Mar 06, 2028

Ports:

Oranjestad → Willemstad → Kralendijk → Saint Barthelemy (Gustavia) → Jost Van Dyke → Virgin Gorda → 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 Maarten (Phillipsburg)

Departs Mar 06, 2028 from Oranjestad, Aruba

View Details

Oceanview From

$7,995

Top Picks Rank: 5

7-night caribbean cruise

$2,273

Windstar Cruises – Wind Surf

4.7 (148)

5 Star

78%

4 Star

12%

3 Star

2 Star

1 Star

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

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,273

Top Picks Rank: 5

7-night caribbean cruise

$2,341

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

2 Star

1 Star

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

Departs Mar 13, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,341

Top Picks Rank: 5

14-night caribbean cruise

$5,582

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

2 Star

1 Star

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

Departs Mar 13, 2028 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,582

Top Picks Rank: 5

7-night caribbean cruise

$2,373

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

2 Star

1 Star

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

Departs Mar 20, 2028 from San Juan, Puerto Rico

Up to 1 deal

View Details

Oceanview From

$2,373

Top Picks Rank: 5

14-night caribbean cruise

$5,582

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

2 Star

1 Star

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

Departs Mar 20, 2028 from San Juan, Puerto Rico

Up to 1 deal

View Details

Oceanview From

$5,582

Top Picks Rank: 5

7-night caribbean cruise

$2,341

Windstar Cruises – Star Pride

4.5 (95)

5 Star

64%

4 Star

26%

3 Star

2 Star

1 Star

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

Departs Mar 27, 2028 from San Juan, Puerto Rico

Up to 1 deal

View Details

Oceanview From

$2,341

Top Picks Rank: 5

Showing 25 of 132 results

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