7-night caribbean cruise

$2,208

Windstar Cruises – Star Pride

4.5 (93)

Date:

Oct 26, 2025 View Other Dates

Ports:

Departs Oct 26, 2025 from San Juan, Puerto Rico

Up to 3 deals including Avoya Exclusives

Suite From

$2,208

7-night caribbean cruise

$2,799

Windstar Cruises – Star Pride

4.5 (93)

Date:

Nov 02, 2025 View Other Dates

Ports:

Departs Nov 02, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$2,799

14-night caribbean cruise

$4,599

Windstar Cruises – Star Pride

4.5 (93)

Date:

Nov 02, 2025 View Other Dates

Ports:

Departs Nov 02, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$4,599

14-night caribbean cruise

$4,099

Windstar Cruises – Star Pride

4.5 (92)

Date:

Nov 09, 2025

Ports:

Departs Nov 09, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$4,099

7-night caribbean cruise

$2,599

Windstar Cruises – Star Pride

4.5 (92)

Date:

Nov 16, 2025 View Other Dates

Ports:

Departs Nov 16, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$2,599

14-night caribbean cruise

$4,099

Windstar Cruises – Star Pride

4.5 (92)

Date:

Nov 16, 2025 View Other Dates

Ports:

Departs Nov 16, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$4,099

14-night caribbean cruise

$4,099

Windstar Cruises – Star Pride

4.5 (91)

Date:

Nov 23, 2025

Ports:

Departs Nov 23, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$4,099

7-night caribbean cruise

$2,599

Windstar Cruises – Star Pride

4.5 (91)

Date:

Nov 30, 2025

Ports:

Departs Nov 30, 2025 from San Juan, Puerto Rico

Up to 2 deals including an Avoya Exclusive

Suite From

$2,599

13-night caribbean cruise

$3,999

Windstar Cruises – Star Pride

4.5 (93)

Date:

Nov 30, 2025

Ports:

Departs Nov 30, 2025 from San Juan, Puerto Rico

Suite From

$3,999

5-night caribbean cruise

$2,099

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 02, 2025

Ports:

Departs Dec 02, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$2,099

12-night caribbean cruise

$3,399

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 02, 2025

Ports:

Departs Dec 02, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$3,399

7-night caribbean cruise

$2,299

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 07, 2025 View Other Dates

Ports:

Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$2,299

14-night caribbean cruise

$3,699

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 07, 2025 View Other Dates

Ports:

Departs Dec 07, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$3,699

6-night caribbean cruise

$2,399

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 14, 2025 View Other Dates

Ports:

Departs Dec 14, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$2,399

14-night caribbean cruise

$4,499

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 14, 2025 View Other Dates

Ports:

Departs Dec 14, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$4,499

8-night caribbean cruise

$2,899

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Dec 20, 2025

Ports:

Departs Dec 20, 2025 from Oranjestad, Aruba

Up to 1 deal including an Avoya Exclusive

Oceanview From

$2,899

7-night caribbean cruise

$2,899

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 21, 2025 View Other Dates

Ports:

Departs Dec 21, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$2,899

14-night caribbean cruise

$4,899

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 21, 2025 View Other Dates

Ports:

Departs Dec 21, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$4,899

6-night caribbean cruise

$2,899

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Dec 28, 2025 View Other Dates

Ports:

Departs Dec 28, 2025 from Saint Maarten (Phillipsburg), Netherlands Antilles

Up to 1 deal

Oceanview From

$2,899

7-night caribbean cruise

$3,099

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Dec 28, 2025

Ports:

Departs Dec 28, 2025 from Bridgetown, Barbados

Up to 2 deals including an Avoya Exclusive

Oceanview From

$3,099

6-night caribbean cruise

$2,599

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Jan 04, 2026 View Other Dates

Ports:

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

Up to 1 deal

Oceanview From

$2,599

10-night caribbean cruise

$3,399

Windstar Cruises – Wind Spirit

4.8 (98)

Date:

Jan 04, 2026

Ports:

Departs Jan 04, 2026 from Bridgetown, Barbados

Up to 1 deal including an Avoya Exclusive

Oceanview From

$3,399

14-night caribbean cruise

$4,199

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Jan 04, 2026

Ports:

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

Up to 1 deal

Oceanview From

$4,199

21-night caribbean cruise

$6,299

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Jan 04, 2026

Ports:

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

Up to 1 deal

Oceanview From

$6,299

28-night caribbean cruise

$9,099

Windstar Cruises – Wind Surf

4.7 (146)

Date:

Jan 04, 2026

Ports:

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

Up to 2 deals including an Avoya Exclusive

Oceanview From

$9,099

Windstar Cruises to Caribbean