Name: 8-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 3427 USD
Availability: InStock
Rating: 4.52 (95 reviews)

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8-night caribbean cruise

$3,427

Windstar Cruises – Star Pride

4.5 (95)

Date:

Oct 20, 2026

Ports:

Boston → Hamilton → Saint George's → San Juan

Departs Oct 20, 2026 from Boston, Massachusetts

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$3,427

7-night caribbean cruise

$3,224

Windstar Cruises – Star Legend

4.5 (86)

Date:

Nov 27, 2026

Ports:

Departs Nov 27, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$3,224

15-night caribbean cruise

$5,455

Windstar Cruises – Star Legend

4.5 (86)

Date:

Nov 27, 2026

Ports:

Departs Nov 27, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,455

14-night caribbean cruise

$5,750

Windstar Cruises – Star Pride

4.5 (95)

Date:

Nov 29, 2026 View Other Dates

Ports:

Departs Nov 29, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$5,750

8-night caribbean cruise

$3,100

Windstar Cruises – Star Legend

4.5 (86)

Date:

Dec 04, 2026

Ports:

Departs Dec 04, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

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Oceanview From

$3,100

16-night caribbean cruise

$6,462

Windstar Cruises – Star Legend

4.5 (86)

Date:

Dec 04, 2026

Ports:

Departs Dec 04, 2026 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,462

7-night caribbean cruise

$3,741

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 06, 2026 View Other Dates

Ports:

Departs Dec 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,741

14-night caribbean cruise

$5,022

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 06, 2026 View Other Dates

Ports:

Departs Dec 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,022

14-night caribbean cruise

$5,608

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 19, 2026

Ports:

Departs Dec 19, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,608

7-night caribbean cruise

$2,866

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 20, 2026 View Other Dates

Ports:

Departs Dec 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$2,866

14-night caribbean cruise

$5,638

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 20, 2026 View Other Dates

Ports:

Departs Dec 20, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,638

7-night caribbean cruise

$3,832

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Dec 26, 2026

Ports:

Departs Dec 26, 2026 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,832

7-night caribbean cruise

$3,913

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,913

14-night caribbean cruise

$6,142

Windstar Cruises – Star Pride

4.5 (95)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,142

7-night caribbean cruise

$3,076

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 03, 2027 View Other Dates

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,076

7-night caribbean cruise

$5,383

Windstar Cruises – Star Pride

4.5 (95)

Date:

Jan 10, 2027 View Other Dates

Ports:

Departs Jan 10, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,383

7-night caribbean cruise

$6,228

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 16, 2027 View Other Dates

Ports:

Departs Jan 16, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Suite From

$6,228

14-night caribbean cruise

$6,420

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 06, 2027 View Other Dates

Ports:

Departs Feb 06, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$6,420

7-night caribbean cruise

$3,848

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 13, 2027 View Other Dates

Ports:

Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,848

14-night caribbean cruise

$5,720

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 13, 2027 View Other Dates

Ports:

Departs Feb 13, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,720

8-night caribbean cruise

$6,740

Windstar Cruises – Star Legend

4.5 (86)

Date:

Feb 22, 2027

Ports:

Departs Feb 22, 2027 from Oranjestad, Aruba

Up to 1 deal

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Oceanview From

$6,740

7-night caribbean cruise

$2,443

Windstar Cruises – Star Legend

4.5 (86)

Date:

Dec 20, 2027

Ports:

Departs Dec 20, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$2,443

14-night caribbean cruise

$3,902

Windstar Cruises – Star Legend

4.5 (86)

Date:

Dec 20, 2027

Ports:

Departs Dec 20, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$3,902

7-night caribbean cruise

$2,411

Windstar Cruises – Star Legend

4.5 (86)

Date:

Dec 27, 2027 View Other Dates

Ports:

Departs Dec 27, 2027 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Inside From

$2,411

11-night caribbean cruise

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Windstar Cruises – Star Pride

4.5 (95)

Date:

Oct 28, 2026

Ports:

Departs Oct 28, 2026 from San Juan, Puerto Rico

Up to 3 deals including an Avoya Exclusive

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Balcony From

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Windstar Cruises to Caribbean