Name: 14-Night Caribbean Cruise
Brand: Windstar Cruises
Price: 4099 USD
Availability: InStock
Rating: 4.52 (93 reviews)

14-night caribbean cruise

$4,099

Windstar Cruises – Star Pride

4.5 (93)

Date:

Dec 13, 2026 View Other Dates

Ports:

Departs Dec 13, 2026 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$4,099

7-night caribbean cruise

$2,699

Windstar Cruises – Star Pride

4.5 (93)

Date:

Dec 20, 2026 View Other Dates

Ports:

Departs Dec 20, 2026 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$2,699

14-night caribbean cruise

$4,399

Windstar Cruises – Star Pride

4.5 (93)

Date:

Dec 20, 2026 View Other Dates

Ports:

Departs Dec 20, 2026 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$4,399

7-night caribbean cruise

$2,899

Windstar Cruises – Star Pride

4.5 (93)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$2,899

14-night caribbean cruise

$4,499

Windstar Cruises – Star Pride

4.5 (93)

Date:

Dec 27, 2026 View Other Dates

Ports:

Departs Dec 27, 2026 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$4,499

7-night caribbean cruise

$2,699

Windstar Cruises – Star Pride

4.5 (93)

Date:

Jan 03, 2027 View Other Dates

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$2,699

14-night caribbean cruise

$4,299

Windstar Cruises – Star Pride

4.5 (93)

Date:

Jan 03, 2027 View Other Dates

Ports:

Departs Jan 03, 2027 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$4,299

7-night caribbean cruise

$2,699

Windstar Cruises – Star Pride

4.5 (93)

Date:

Jan 10, 2027 View Other Dates

Ports:

Departs Jan 10, 2027 from San Juan, Puerto Rico

Up to 1 deal

Oceanview From

$2,699

8-night caribbean cruise

$7,949

Windstar Cruises – Star Seeker

Date:

Jan 15, 2026

Ports:

Miami → Puerto Plata → Samana → Jost Van Dyke → Virgin Gorda → Soper's Hole → San Juan

Departs Jan 15, 2026 from Miami, Florida

Balcony From

$7,949

7-night caribbean cruise

$2,599

Windstar Cruises – Star Legend

4.5 (86)

Date:

Nov 27, 2026

Ports:

Departs Nov 27, 2026 from Bridgetown, Barbados

Oceanview From

$2,599

7-night caribbean cruise

$2,699

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Dec 19, 2026

Ports:

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

Oceanview From

$2,699

14-night caribbean cruise

$4,299

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Dec 19, 2026

Ports:

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

Oceanview From

$4,299

7-night caribbean cruise

$2,699

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Dec 26, 2026

Ports:

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

Oceanview From

$2,699

14-night caribbean cruise

$4,099

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Dec 26, 2026

Ports:

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

Oceanview From

$4,099

7-night caribbean cruise

$2,499

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 02, 2027 View Other Dates

Ports:

Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$2,499

14-night caribbean cruise

$3,999

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 02, 2027

Ports:

Departs Jan 02, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$3,999

7-night caribbean cruise

$2,499

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 09, 2027

Ports:

Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$2,499

14-night caribbean cruise

$3,999

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 09, 2027

Ports:

Departs Jan 09, 2027 from Saint Maarten (Phillipsburg), Netherlands Antilles

Oceanview From

$3,999

7-night caribbean cruise

$2,499

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 16, 2027 View Other Dates

Ports:

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

Oceanview From

$2,499

14-night caribbean cruise

$3,999

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 16, 2027 View Other Dates

Ports:

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

Oceanview From

$3,999

7-night caribbean cruise

$2,599

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 23, 2027 View Other Dates

Ports:

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

Oceanview From

$2,599

14-night caribbean cruise

$4,099

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 23, 2027

Ports:

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

Oceanview From

$4,099

7-night caribbean cruise

$2,599

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 30, 2027 View Other Dates

Ports:

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

Oceanview From

$2,599

14-night caribbean cruise

$4,099

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Jan 30, 2027 View Other Dates

Ports:

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

Oceanview From

$4,099

7-night caribbean cruise

$2,599

Windstar Cruises – Wind Surf

4.7 (147)

Date:

Feb 06, 2027 View Other Dates

Ports:

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

Oceanview From

$2,599

Windstar Cruises to Caribbean