Name: 10-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 5020 USD
Availability: InStock
Rating: 4.76 (100 reviews)

10-night caribbean cruise

$5,020

Windstar Cruises – Wind Spirit

4.8 (100)

Date:

Jan 04, 2026

Ports:

Departs Jan 04, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$5,020

7-night caribbean cruise

$6,910

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 04, 2026

Ports:

Departs Jan 04, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

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Suite From

$6,910

7-night caribbean cruise

$7,136

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 11, 2026

Ports:

Departs Jan 11, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

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Suite From

$7,136

8-night caribbean cruise

$6,796

Windstar Cruises – Star Seeker

Date:

Jan 15, 2026

Ports:

Miami → Puerto Plata → Samana → Jost Van Dyke → Virgin Gorda → Sopers Hole → San Juan

Departs Jan 15, 2026 from Miami, Florida

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$6,796

7-night caribbean cruise

$4,222

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 18, 2026

Ports:

Departs Jan 18, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$4,222

14-night caribbean cruise

$8,247

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 18, 2026

Ports:

Departs Jan 18, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$8,247

7-night caribbean cruise

$7,562

Windstar Cruises – Star Seeker

Date:

Jan 23, 2026 View Other Dates

Ports:

Departs Jan 23, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Balcony From

$7,562

7-night caribbean cruise

$4,424

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 25, 2026

Ports:

Departs Jan 25, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$4,424

15-night caribbean cruise

$7,766

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 25, 2026

Ports:

Departs Jan 25, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$7,766

7-night caribbean cruise

$8,427

Windstar Cruises – Star Seeker

Date:

Jan 30, 2026 View Other Dates

Ports:

Departs Jan 30, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Suite From

$8,427

7-night caribbean cruise

$5,927

Windstar Cruises – Star Seeker

Date:

Feb 13, 2026 View Other Dates

Ports:

Departs Feb 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$5,927

11-night caribbean cruise

$4,863

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 17, 2026

Ports:

Departs Feb 17, 2026 from Cozumel, Mexico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$4,863

18-night caribbean cruise

$8,965

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 17, 2026

Ports:

Departs Feb 17, 2026 from Cozumel, Mexico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$8,965

7-night caribbean cruise

$7,312

Windstar Cruises – Star Seeker

Date:

Feb 20, 2026

Ports:

Departs Feb 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Balcony From

$7,312

7-night caribbean cruise

$5,836

Windstar Cruises – Star Seeker

Date:

Feb 27, 2026

Ports:

Departs Feb 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$5,836

7-night caribbean cruise

$4,351

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 28, 2026

Ports:

Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$4,351

14-night caribbean cruise

$6,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 28, 2026

Ports:

Departs Feb 28, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,919

7-night caribbean cruise

$6,662

Windstar Cruises – Star Seeker

Date:

Mar 06, 2026 View Other Dates

Ports:

Departs Mar 06, 2026 from San Juan, Puerto Rico

Up to 1 deal

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Oceanview From

$6,662

7-night caribbean cruise

$3,867

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 07, 2026

Ports:

Departs Mar 07, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$3,867

8-night caribbean cruise

$4,716

Windstar Cruises – Wind Spirit

4.8 (100)

Date:

Mar 07, 2026

Ports:

Departs Mar 07, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$4,716

7-night caribbean cruise

$5,733

Windstar Cruises – Star Seeker

Date:

Mar 13, 2026

Ports:

Departs Mar 13, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$5,733

7-night caribbean cruise

$3,767

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 14, 2026

Ports:

Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,767

14-night caribbean cruise

$6,819

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 14, 2026

Ports:

Departs Mar 14, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$6,819

7-night caribbean cruise

$2,739

Windstar Cruises – Star Pride

4.5 (95)

Date:

Mar 15, 2026

Ports:

Departs Mar 15, 2026 from Oranjestad, Aruba

Up to 3 deals including Avoya Exclusives

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Oceanview From

$2,739

6-night caribbean cruise

$4,416

Windstar Cruises – Wind Spirit

4.8 (100)

Date:

Mar 15, 2026

Ports:

Departs Mar 15, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,416

Windstar Cruises to Caribbean