Name: 14-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 5419 USD
Availability: InStock
Rating: 4.66 (148 reviews)

14-night caribbean cruise

$5,419

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

Oceanview From

$5,419

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 23, 2027 View Other Dates

Ports:

Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,051

14-night caribbean cruise

$4,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 23, 2027

Ports:

Departs Jan 23, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,919

7-night caribbean cruise

$3,067

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 30, 2027 View Other Dates

Ports:

Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,067

14-night caribbean cruise

$4,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Jan 30, 2027 View Other Dates

Ports:

Departs Jan 30, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,919

7-night caribbean cruise

$3,051

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

$3,051

14-night caribbean cruise

$4,919

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

$4,919

7-night caribbean cruise

$3,167

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

$3,167

14-night caribbean cruise

$5,019

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

$5,019

7-night caribbean cruise

$3,151

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 20, 2027 View Other Dates

Ports:

Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,151

14-night caribbean cruise

$5,119

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 20, 2027

Ports:

Departs Feb 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,119

7-night caribbean cruise

$3,267

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 27, 2027

Ports:

Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,267

14-night caribbean cruise

$5,019

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Feb 27, 2027

Ports:

Departs Feb 27, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$5,019

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 06, 2027 View Other Dates

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,051

14-night caribbean cruise

$4,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 06, 2027 View Other Dates

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,919

7-night caribbean cruise

$3,067

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 13, 2027 View Other Dates

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,067

14-night caribbean cruise

$4,919

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 13, 2027 View Other Dates

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,919

7-night caribbean cruise

$3,051

Windstar Cruises – Wind Surf

4.7 (148)

Date:

Mar 20, 2027 View Other Dates

Ports:

Departs Mar 20, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$3,051

7-night caribbean cruise

$7,312

Windstar Cruises – Star Seeker

Date:

Feb 06, 2026 View Other Dates

Ports:

Departs Feb 06, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Balcony From

$7,312

7-night caribbean cruise

$4,360

Windstar Cruises – Wind Spirit

4.8 (100)

Date:

Feb 14, 2026

Ports:

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

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$4,360

24-night caribbean cruise

$15,438

Windstar Cruises – Star Seeker

Date:

Mar 27, 2026

Ports:

Departs Mar 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$15,438

49-night caribbean cruise

$28,243

Windstar Cruises – Star Seeker

Date:

Mar 27, 2026

Ports:

Departs Mar 27, 2026 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

View Details

Oceanview From

$28,243

28-night caribbean cruise

$15,895

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

View Details

Oceanview From

$15,895

55-night caribbean cruise

$27,646

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

View Details

Oceanview From

$27,646

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

View Details

Oceanview From

$8,247

Windstar Cruises to Caribbean